Antilles2027

6 countries · 15 jurisdictions · 19 regions · 35 days

Five weeks down the Antilles.
Two cabins are open.

from Saturday27 March 2027to Saturday1 May 2027

A Lagoon 43 in the eastern Caribbean · out of Le Marin, Martinique · skipper and cook aboard.

€12,500 a person for the whole trip · two sharing a cabin ↓ scroll

Two are taken. Two cabins are open, and I'm calling in friends.

The host and the skipper sitting together on the stern step of a boat, bare feet on the deck, deep blue water behind them.

Me and the skipper.

I have chartered a catamaran out of Le Marin, Martinique for five weeks next spring, hired a professional skipper and a cook, and spent a while planning a route that collects as much of the Caribbean as 35 days will physically allow. The boat has four double cabins. I am in one of them and a friend has taken another. Two are still open, so I am looking for two more parties. I am inviting people rather than advertising.

That is the whole pitch. If five weeks of Caribbean trade-wind sailing, fifteen countries and a different anchorage most nights sounds like your kind of spring, read the rest and tell me. If you count countries or NomadMania regions, the route was built for you specifically. If you have never set foot on a boat, that is fine too — there is a skipper aboard and nothing is asked of you.

The dates are fixed: Saturday 27 March to Saturday 1 May 2027, thirty-five days, out of Le Marin and back to Le Marin. What I want to fill first is a cabin for the whole trip. Take one and split it however you like: it is yours from the first day to the last, and who sleeps in it is your business. One person for the lot. A family handing it on. A company perk that sends a different colleague out at each handover. There are five handover ports along the way and every one of them is an island with a proper airport, so flying in and out is a ticket, not a project.

~970nautical miles

5handover ports

2cabins open

The marina at Le Marin, Martinique, in the evening: rows of moored catamarans, masts against a warm sky.

Le Marin, where the boat lives and where the first Saturday starts.

The deal

Take a whole cabin. Split it however you like.

This is what I want to fill first: a cabin for all thirty-five days, at one price, and who sleeps in it is your business. Hand it on at any of the five handover ports; every one of them is an island with a proper airport.

€12,500a person, all 35 days, two sharing

€25,000the whole cabin, both berths

For one, or two

The whole way

Five weeks, fifteen countries, one price. Take the cabin and decide later who else is in it.

For a family

Hand it on

Parents for the first stretch, then the grown-up kids, then the grandparents or the friends. Hand over at Grenada, Martinique, Guadeloupe, Antigua or Sint Maarten — all of them an island with an airport.

For a company

A different colleague at each handover

One cabin as a perk, three or four people over the spring, Starlink aboard for the ones who need to keep a working day. Book once, and the rota is yours.

Handovers: 27 Mar board at Le Marin · 3 Apr Grenada · 7 Apr Martinique · 13 Apr Guadeloupe · 16 Apr Antigua · 25 Apr Sint Maarten · 1 May back to Le Marin. The swap is a flight, not a project.

Take a cabin What the price includes →

The route

Down the chain, and back up it

Martinique to Grenada, north to Anguilla, then 269 nautical miles home — about 970 nautical miles in all, mostly day hops, with one overnight going south and a two-night passage coming back. Tap an island for what we do there; tap a leg or a number to jump to it. Press Weather for what late March and April actually do to this water.

Drawn for this page from published island positions and small-scale bathymetry, then simplified. Soundings in metres, dashed line is the 100-fathom contour. The weather layer is not drawn but measured: station thermometers and ERA5 rainfall over ten seasons, MERRA-2 wind, ECMWF sea temperature over three, all for 27 March to 1 May. Not for navigation.

What is on the chart

the 100-fathom line — inside it the boat has a bottom to anchor on
soundings in metres: Saba and Statia sit on seamounts with deep water right up to the rock
the ten dive sites in the table further down
the trade, east to east-north-east, every day of the five weeks
the gaps between the islands, where it accelerates
the wind shadow behind a high island: light, fluky, then a squeeze at each end
the north swell, which arrives from a gale two thousand miles away and empties a west-facing anchorage — about one day in thirty this late in the season, against one in twenty in January

Between Antigua and Anguilla — the top of the chart, and the slowest, densest stretch of the route — there are nine separate jurisdictions in 78 nautical miles. Three countries own pieces of it, one island is split between two of them, and you can usually see the next border from the anchorage you are in.

Five weeks

Thirty-five days, six legs

The route breaks into six legs, from three days to nine, and each one ends at an island with an international airport. The whole thing is what I am selling; the legs are how it is put together, and where a cabin can change hands.

Admiralty Bay, Bequia, from the hill: yachts at anchor and the town along the shore.

Leg 1Sat 27 Mar → Sat 3 AprFDFGND

Martinique to Grenada, down the Grenadines

Bequia, Mustique, Tobago Cays, Carriacou · 161 nm · 7 days · one night passage

Board at Le Marin on the Saturday evening, provision, and shake down along Martinique's west coast. Then an overnight passage south to Bequia — the one night sail of the trip and a good one: broad reach, warm, phosphorescence off the transom.

Admiralty Bay, Mustique, Canouan, then the Tobago Cays: a horseshoe reef with nothing behind it but open Atlantic, turtles on the inside, and the best snorkelling in the eastern Caribbean. Out through Mayreau and Union, then Carriacou and down to Grenada.

The longest leg in days and the shortest in miles — 23 nautical miles a day, with the trades abaft the beam nine days in ten. One thing to know going in: Easter Sunday falls on 28 March, the second day, and Easter week is when Bequia and the Tobago Cays are at their fullest of the year.

What it is — the classic Caribbean postcard leg, the easiest sailing of the route, and the only night passage going south.

Night sailing: the deck in darkness, red instrument light, a sail against a sky thick with stars.

Two or three boats lying to anchor in turquoise water off a small green Grenadines island.

An empty curving white beach on an uninhabited Grenadines island, palms leaning over clear shallows.

A fisherman alongside in a small open boat holding up lobsters to sell, the reef behind him.

🇲🇶 🇻🇨 🇬🇩 3 regions

The two Pitons of Saint Lucia from the water off Soufrière on a clear morning.

Leg 2Sat 3 → Wed 7 AprGNDFDF

Grenada back up to Martinique

Molinière, Chatham Bay, St Vincent, the Pitons · 157 nm · 4 days · upwind

Grenada first — the underwater sculpture park at Molinière, St George's, the south-coast anchorages — then we turn and work north. Chatham Bay on Union, back through the Grenadines by a different set of anchorages, then St Vincent itself, and St Lucia under the Pitons at Soufrière.

This is the shortest leg and the hardest-working one: 157 miles north in four days is 39 a day, and with the trade at 082° the course sits 63° off the wind — four days in ten are a genuine beat. It is the best stretch of the route to learn to actually sail rather than be a passenger, and the one with no slack in it for a bad forecast.

What it is — sailing properly, and the Pitons. Note that St Lucia is the leg that needs the visa.

St George’s, Grenada, from the water: the Carenage lined with pastel buildings and red roofs up the hill.

Concrete human figures standing on a shallow sandy seabed, encrusted with algae, divers’ bubbles above.

A Grenada market stall of nutmeg, mace, cinnamon bark and cocoa, a vendor’s hands sorting them.

Chatham Bay on Union Island: an empty anchorage, steep green hills, no buildings.

🇬🇩 🇻🇨 🇱🇨 🇲🇶 3 regions

A boatman rowing up the Indian River in Dominica beneath overhanging swamp bloodwood roots.

Leg 3Wed 7 → Tue 13 AprFDFPTP

Martinique to Guadeloupe, by Dominica

St Pierre, Indian River, Champagne Reef, Les Saintes · 117 nm · 6 days

North past Saint-Pierre, the town Mont Pelée destroyed in 1902, then across to Dominica — the island that still has an actual jungle. Prince Rupert Bay, a boatman rowing you up the Indian River, waterfalls and hot springs inland, Champagne Reef where volcanic gas bubbles up through the coral.

Then Les Saintes: French bakeries, a fort on a hill, and Pain de Sucre, which is the anchorage people still talk about years later.

Nineteen miles a day and the best-angled sailing on the route — 88% of days fall between 60° and 120° off the wind. It is also the wettest stretch, at roughly double the Grenadines’ rainfall, because Dominica and Guadeloupe make their own weather.

What it is — hiking, rainforest and diving. The greenest leg by a distance.

Saint-Pierre, Martinique, from the water with Mont Pelée rising behind the town in cloud.

A steaming hot spring pool in a rock basin in the Dominica rainforest, tree ferns closing over it.

A tall waterfall in the Dominica rainforest with two people at the plunge pool for scale.

The Pain de Sucre anchorage at Les Saintes from above, yachts in clear water beside a rounded headland.

🇲🇶 🇩🇲 🇬🇵 2 regions

Plymouth, Montserrat, half buried in grey ash, seen from the water with the volcano behind it.

Leg 4Tue 13 → Fri 16 AprPTPANU

Across the volcano gap to Antigua

The Montserrat exclusion zone, Nelson's Dockyard · 80 nm · 3 days

Three days and eighty miles, straight up the outside. North past Montserrat, where half the island is still a volcanic exclusion zone and you can see the buried capital of Plymouth from the water — the boat has to stand further off than the rhumb line, so the gap is longer than it looks on the chart.

Then Antigua: Nelson’s Dockyard, the Georgian pillars, and Nonsuch Bay. This is also the likeliest stretch of the whole route to run out of wind — one day in eight averages under ten knots, more than anywhere else on the chart.

What it is — the shortest leg, the biggest single sight, and the one where the engine most often goes on.

The Georgian pillars of the old sail loft at Nelson’s Dockyard with yacht masts directly behind them.

Nonsuch Bay, Antigua, from above: turquoise water inside a white reef line across the mouth of the bay.

Deshaies, Guadeloupe, at first light: yachts on moorings in a steep green bay with the village along the shore.

A catamaran under full sail on open water with the grey volcanic bulk of Montserrat on the horizon behind it.

🇬🇵 🇲🇸 🇦🇬 2 regions

An empty pink-sand beach on Barbuda running dead straight to the horizon.

Leg 5Fri 16 → Sun 25 AprANUSXM

Antigua to Sint Maarten, the densest stretch on the map

Barbuda, St Kitts, Nevis, Statia, Saba, St Barth · 184 nm · 9 days · 7 regions

Up to Barbuda first: seventeen miles of empty pink sand, and the frigate-bird colony in Codrington Lagoon. Then the run that makes this trip what it is — St Kitts, Nevis, Sint Eustatius, Saba and St Barth, five separate places within sight of one another, most a two-hour hop apart.

Saba is a single volcanic cone rising straight out of deep water with no harbour and no beach, one of the strangest islands in the Atlantic, and the diving off it is exceptional. Seven new regions in nine days.

Nine days for 184 miles is the loosest schedule of the route, and it wants to be: this is where the slack lives. Three-quarters of the days run abaft the beam, and by the second half of April the north swell that closes Saba and Statia in winter has all but gone.

What it is — the collector’s leg. Nothing else on the route comes close for countries per mile.

Frigate birds nesting in low mangrove in Codrington Lagoon, Barbuda, several males with scarlet pouches inflated.

Brimstone Hill Fortress on St Kitts from the sea: dark stone ramparts high on a green headland.

Nevis Peak from the sea: a symmetrical green cone with cloud on the summit.

Windwardside on Saba: white houses with red roofs on a steep green mountainside under low cloud.

🇦🇬 🇰🇳 🇧🇶 🇧🇱 🇸🇽 7 regions

Open ocean from the deck under sail: Atlantic swell running, no land, the boat working.

Leg 6Sun 25 Apr → Sat 1 MaySXMFDF

Sint Maarten to Martinique, the long way home

Saint-Martin, Anguilla, then the passage south · 269 nm · 6 days

The only island in the world split between two countries you can walk across in an afternoon: we clear into Dutch Sint Maarten and French Saint-Martin separately, because they separately are. Then Anguilla and Road Bay at the top of the chain, before turning south for the passage back to Martinique.

That passage is not the downwind slide people expect. Martinique sits two degrees of longitude east of Sint Maarten, so the course runs south-east into an easterly trade: 269 miles at an average 58° off the wind, with nearly half the days a beat. Two nights at sea, and the only genuinely offshore water of the trip.

What it is — the passage leg, and the one to be honest about: this is sailing, not sightseeing. Starlink runs email-only offshore.

The stone border marker on the road between Sint Maarten and Saint-Martin.

Shoal Bay, Anguilla: a long empty white beach meeting very pale turquoise water.

🇸🇽 🇲🇫 🇦🇮 🇲🇶 2 regions

The cove at Pain de Sucre, Les Saintes: pale sand between two green headlands, small boats at anchor.

Pinney’s Beach, Nevis: a long curve of pale sand under coconut palms with Nevis Peak behind.

Oranjestad, Sint Eustatius, from the water: lower-town ruins at the foot of the cliff, the Quill behind.

Gustavia harbour on St Barth in the evening, yachts moored stern-to along the quay.

Four more, larger: the cove at Pain de Sucre on leg 3, then three from the leg that collects seven regions — Pinney's Beach on Nevis, the lower town at Oranjestad on Statia, and Gustavia in the evening.

Weather moves things. Late March and April mean steady east to east-north-east trades at 11–18 knots — lighter and far steadier than the winter, with roughly one day in seventy over twenty knots and one in fifteen under ten. The long-period swell out of the North Atlantic that makes Saba and Statia unusable for a day or two is down to about one day in thirty, from one in twenty in January. When an anchorage does close we reorder within the leg. The handover dates are fixed, because people have flights; everything between them is not. Two to three of the 35 days are held as weather reserve.

The boat

A catamaran, not a yacht that leans

A Lagoon 43 built in 2026: two hulls, flat, 13.9 metres long and 7.7 wide. Nothing about five weeks aboard requires you to be brave.

A Lagoon 43 at anchor seen head-on from the water: two white hulls, the flat bridge deck between them, mast and furled sails above.

The cockpit table laid for a meal, seen from inside the saloon through the open door, with the sea and a green island beyond.

A double guest cabin in the hull: the berth under a long hull window, pale oak lining, a reading shelf above.

A Lagoon 43 at anchor photographed from the masthead looking straight down: both hulls, the cockpit, and the tender and paddleboards alongside in clear water.

Four double cabins, and every one of them has its own bathroom with a separate heads. Three of them are guest cabins; the skipper and the cook have the forepeak cabins, so nobody is sleeping in a corridor and no guest cabin is taken by crew.

The cockpit is the living room. It is shaded, outdoors, and big enough for ten of us to eat at the same table — most of the five weeks happens there rather than below.

Two 57 hp Yanmars for when the wind stops, a dinghy and outboard for reefs and getting ashore, and 1.3 m of draft, which is shallow enough to anchor close in. The 43 is certified CE category A — ocean — for up to twelve people, which is the box leg 6’s two hundred and seventy miles of open water has to tick. There will be at most ten of us.

Type: Lagoon 43 cruising catamaran, built 2026
Design: VPLP naval architecture, exterior by Patrick le Quément, interior by Nauta
Length: 13.9 m overall, 12.8 m hull
Beam: 7.7 m
Draft: 1.31 m
Cabins: Four doubles, each with its own bathroom and separate heads
Crew: Professional skipper and a cook, both in the forepeak cabins
Engines: Two 57 hp Yanmar diesels
Sail area: 105 m² upwind
Tanks: 630 L water, 570 L fuel
Certification: CE category A — ocean — for up to 12 people
Tender: Dinghy and outboard included
Aboard: Ten people: eight guests, skipper, cook

Three decks, one boat

Lagoon’s own drawing of the 43, cut at three levels. It is the same render every time — same boat, same angle, same frame — so the tabs peel a layer off rather than change the subject. Bow is to the right.

Deck & helm Saloon & cockpit Cabins

Lagoon 43 deck plan seen from directly above: the aft steps and cockpit with its table, the raised helm to port, side decks running forward, the forward lounging area and the trampolines at the bow.

The same Lagoon 43 with the coachroof cut away: the saloon on the bridge deck between the hulls, galley along the port side, dining settee to starboard, opening straight out to the cockpit at one level.

The same Lagoon 43 cut at hull level in the four-cabin version: two double cabins in each hull, one forward and one aft, each with its own bathroom.

Two teak sugar-scoops at the stern: that is how you get in and out of the dinghy and how you go swimming. Forward of them the cockpit sits under a fixed hardtop — shade from breakfast until sunset, which over five weeks matters more than almost anything else on the boat. The helm is raised on the port side — Lagoon calls it the flybridge — with every line led back to it, and a few steps come up to it from the saloon, so whoever is steering is still in the conversation rather than exiled to a corner. Past the mast there is a second, forward cockpit with its own cushions, and then the trampolines.

Lift the hardtop off. The galley runs along the port side of the saloon — fridge, four-burner hob, sink under a window — so whoever is cooking is in the room with everyone else rather than shut below. The dining settee is to starboard. And the bridge deck is one level: the door between saloon and cockpit slides away and the two become a single room, which is why almost every meal of the five weeks happens outside and the saloon is mostly somewhere to go when it rains. Lagoon also builds a version of this deck that folds saloon and cockpit into one table for twelve.

Cut at hull level. Two double cabins in each hull, one forward and one aft — four in all, and each has its own bathroom off it, with the toilet in a separate compartment from the shower on the forward pair. Between them the companionway comes down from the saloon with the hanging lockers and a washbasin. Nobody shares a bathroom, and nobody walks through anybody’s cabin to get anywhere. All four are guest cabins — I am in one, one is taken and two are still open — because the skipper and the cook sleep in the forepeaks, right forward at the bows.

Drawings: Lagoon, the builder of the boat. The hull plan is the four-cabin version, which is the one we have.

Saba from the sea: one steep volcanic island rising out of deep water, cliffs straight down, no beach, cloud on the summit.

Underwater

Snorkelling every day, diving if you want it

The route passes some of the best diving in the eastern Caribbean — Saba above all, a volcanic cone rising straight out of deep water with no harbour and no beach — and it passes it from the water: we arrive by boat at sites most visitors reach on a day trip from a hotel. If you dive, say so and we will fit it in. If you do not, the snorkelling is the better half of it anyway.

Two divers small against a deep pinnacle wall of sponge and soft coral, blue water behind them.

Columns of volcanic gas bubbles rising through the reef at Champagne, Dominica, shot from below toward the surface.

If you want to dive

There is no compressor and no tank storage aboard, so dives are booked with local operators island by island and the skipper arranges them — normal for a charter catamaran. Certified divers bring a card and logbook; beginners can do a Discover Scuba almost anywhere on the route.

Budget roughly €70–90 pp for a single tank with a local shop and €120–160 pp for a two-tank morning, gear included. That is out of pocket, not in the cabin price.

What is actually down there, and alongside

Spinner dolphins riding the bow wave, seen from the bow looking down at them breaking the surface.

A small pod of spotted dolphins in clear deep blue water with sunlight shafts from the surface.

A sperm whale at the surface in deep water off Dominica, its blow drifting, seen from a distance.

A hawksbill turtle swimming over a shallow reef, its shell patterning sharp, small fish around it.

A school of silver and yellow reef fish swirling over sea fans and brain coral in shallow water.

A southern stingray gliding low over rippled pale sand in shallow water.

A nurse shark resting under a coral ledge, photographed at a distance.

A green turtle grazing on seagrass in shallow clear water.

Dolphins on the bow wave and underwater, a sperm whale off Dominica, a hawksbill, a reef school, a stingray, a nurse shark, a green turtle in the Cays. None of this is scheduled and none of it is promised; it is what the water along this route has in it.

Snorkelling is included, and it is excellent here

Masks, snorkels and fins are aboard for everyone, and the dinghy exists precisely to drop people on a reef. Tobago Cays, Champagne Reef, Molinière and the Pillars of Hercules are all snorkel sites: the turtles, the bubbles and the sculptures do not require a certification card.

A shallow coral garden seen from just under the surface while snorkelling, the silver of the surface above.

People swimming and snorkelling beside the catamaran at anchor, one of them stepping in off the transom.

Left, two metres down off the dinghy. Right, the swimming that happens most afternoons without anyone planning it.

A humpback whale breaching almost clear of the water in open blue ocean, white water falling away from it, a hazy island on the horizon.

Whales

Sperm whales all year, humpbacks at the end of theirs

A family of sperm whales lives off Dominica permanently, and April finds them at close to the winter rate. The humpbacks that calve in these islands are on their way out by then: we catch the tail of that season, not the peak.

This is the part of the route I am least able to promise and most looking forward to. The Lesser Antilles sit on the humpback calving grounds: the animals that spend the summer feeding off Iceland and Newfoundland come south to give birth in warm shallow water, They are in these islands from December into May, the peak is February and March, and our first days are the last of it — so a humpback on this trip is luck rather than a schedule. The French islands — Martinique, Guadeloupe, Saint-Barthélemy, Saint-Martin — are covered by Sanctuaire Agoa, a marine mammal sanctuary in which twenty-three cetacean species have been recorded.

Off the west coast of Dominica there is something rarer, and far more dependable. A population of sperm whales lives there permanently rather than passing through — families of females and calves that stay in the same stretch of deep water year after year, which is why researchers have been able to study individual animals across decades. The island drops into deep ocean immediately offshore, so they are close in. Sightings peak from November to March and hold through April and May at close to the same rate. We are on that coast on leg 3.

Between the islands the everyday version is dolphins. Spinners, bottlenose and spotted dolphins turn up on the bow wave often enough that people stop putting their coffee down for it by week three. Short-finned pilot whales are regular in the deep water on the Atlantic side of the chain.

A humpback mother and her calf underwater in clear blue water, the calf tucked close above her head, sunlight coming down from the surface.

A small group of sperm whales hanging vertically in deep blue water, heads up and tails down, resting.

A whale's tail fluke lifting clear of a calm sea as it dives, water streaming off the trailing edge, a volcanic island silhouetted in evening light behind.

Spinner dolphins riding the bow wave of a sailing catamaran at sunset, seen looking down over the bow.

A mother and calf, sperm whales resting upright in the deep, a fluke going down at the end of the day, and the dolphins that turn up on the bow without being asked. Nothing here is scheduled and nothing is promised — this is what the season has in it.

What can actually be booked

From Roseau in Dominica, Dive Dominica runs a three-hour whale watch for US$69 a head, or about US$690 for the whole boat up to six people. They drop a hydrophone, listen for the clicks, and go to them. It is observation from the boat: nobody gets in the water.

Getting in the water with sperm whales is now a different proposition entirely. Dominica is turning its west coast into a sperm whale reserve of roughly 1,231 km²: the government announced parliamentary approval in October 2025, and later reporting says the law was then held up. The practical position is not in doubt either way — in-water encounters run only through a permitted operator. Those operators put the government permit at US$6,000 and sell it as a multi-day expedition from around US$5,500 a couple. Their seasons sell out a year ahead.

Which means it is not something we can bolt onto an afternoon at anchor. If swimming with sperm whales is the reason you are coming, say so early and plan it as its own trip — I would rather write that here than have you ask me somewhere off Dominica.

23cetacean species recorded in Sanctuaire Agoa

Dec–Mayhumpbacks in these islands; we arrive for the last weeks of it

1,231 km²Dominica's sperm whale reserve

One uncomfortable thing, left in

Bequia, our second stop, still holds an aboriginal-subsistence whaling quota under the International Whaling Commission: up to four humpbacks a year, taken with hand-thrown harpoons from open sailing boats. The limit is rarely reached and in some years there is no catch at all. On the Port Elizabeth waterfront the Whaleboner bar has an entrance arch built from two whale ribs and bar stools made of vertebrae.

You are entitled to whatever you think about that. It is part of what this island chain actually is, and on the first leg you will be standing in the middle of it.

And then

Everything else we could do, if you want to

Thirty-five days is a lot of days. None of this is in the price and none of it is compulsory — it is the menu for the days you want to be something.

The route was built around anchorages, not activities, which turns out to be the useful way round: almost everything below is something you walk to from a dinghy, and a handful of them are things you could not do at all if you were not arriving by sea. I have put the leg beside each one so you can see where on the route it falls.

Prices are what the operator published when this page was written, in their own currency, and they are out of pocket rather than in the cabin price. Some will have moved by the spring of 2027. Where something is not guaranteed — a volcano hazard level, an operator who may not be running that week — it says so on the card rather than in the small print.

One way

Full

The Boiling Lake on the Tuesday, a helicopter over a buried city on the Thursday, a distillery in full harvest on the Saturday. Five weeks is enough to do a serious thing every few days and still sail the whole chain. If that is what you want, tell me early — the guided walks and the aircraft are the two things that need booking ahead.

The other way

Empty

Or none of it. Swim off the transom, read, eat what the cook made, watch the light go, sleep. Several of the best days on a trip like this have nothing in them at all, and nobody aboard will think less of you for taking the whole five weeks that way.

Saba

Land on the shortest commercial runway in the world

Winair's Twin Otter drops onto a 400-metre strip cut into a clifftop, deep water off both ends. It is a scheduled passenger flight from Sint Maarten, not a stunt: fifteen minutes each way, and the landing is the point.

from US$112 one way

Leg 5

Looking down from a helicopter on the buried town of Plymouth, rooftops half swallowed by grey volcanic ash, the steaming volcano dome behind.

Montserrat

Fly over the exclusion zone

Soufrière Hills erupted in 1995 and buried Plymouth, the capital, in 1997; the southern half of the island has been closed by law ever since and nobody lives in it. From the air you get the town under the ash and the lava dome at the summit — the mound of stiff lava that piles up over the vent instead of flowing away. CalvinAir's six-seat H130 out of Antigua, forty-five minutes with the pilot talking. We pass Plymouth from the water too, but not this close and not from above.

US$355 pp, six seats

Leg 4

Saint Lucia

The Pitons from a helicopter

The Pitons are two volcanic plugs rising straight out of the sea beside Soufrière on the west coast of St Lucia — Gros Piton at 770 m and Petit Piton at 743 m, a UNESCO World Heritage site. Twenty minutes out of Castries over Marigot Bay, the rainforest and both of them. We will already have anchored under them; this is the other angle.

US$197 pp, four minimum

Leg 2

A tandem paraglider over a green Caribbean hillside, a turquoise bay and anchored boats far below.

Martinique

Tandem paraglide off the hills above the boat

Martinique Parapente launches from Morne Gommier and Morne Larcher, both within sight of where we start. Twenty to thirty minutes in the air, and the only flying on this list you can reach on foot from the anchorage.

around €70–100

Legs 1, 3, 6

A skydiver in freefall above a Caribbean headland, reef and open ocean below.

Guadeloupe

Jump out of a plane over Pointe des Châteaux

Caraïbe Parachutisme at Saint-François, exit at 3,000 m, about thirty seconds of freefall over the reef and the headland. It is the only drop zone on the entire route.

around €280–300

Legs 3–4

Dominica

Walk to the Boiling Lake

Eight to ten hours through the Valley of Desolation — bare sulphur ground, fumaroles, no shade — to the second-largest boiling lake on earth. A certified guide is required by law, and rightly.

US$100–150 pp guided Needs a night at Roseau: the trailhead is 90 minutes from our anchorage at Prince Rupert Bay.

Leg 3

Walkers on a steep rooted trail near the summit of a volcanic peak, the sea far below through the trees.

Saint Lucia

Climb Gros Piton

Four to six hours up the one you have been looking at all week. A certified guide at the gate is mandatory. Petit Piton is steeper, twice the price, and not a casual undertaking.

about US$50 pp plus guide

Leg 2

A street in an abandoned town buried to the first-floor windows in grey volcanic ash, a green volcano behind.

Montserrat

Walk into a buried capital

Plymouth has been under ash since 1997. Escorted visits run with a certified guide under permit, and only when the hazard level allows it.

about US$120 pp, full day Never guaranteed. The Volcano Observatory sets the hazard level and it can close the zone that week.

Leg 4

The ruined stone walls of a theatre in a Caribbean town with a large green volcano rising directly behind it.

Martinique

Mont Pelée, and the town it erased

Five to seven hours up the volcano that killed a town of twenty-eight thousand in about ninety seconds in 1902. The theatre ruins and the jail cell of the man who survived it are a walk from the water at Saint-Pierre.

guided summit around €85; museum €8

Leg 3

A steaming volcanic summit dome, bare grey rock and yellow sulphur, cloud below the trail.

Guadeloupe

The highest point in the Lesser Antilles

La Soufrière, 1,467 m, about an hour up from the Savane à Mulets car park to a steaming summit dome. Free, and no guide required on the summit trail — though the active craters themselves need an accredited guide.

free

Legs 3–4

A long stone staircase climbing through dripping cloud forest, tree ferns and mist on both sides.

Saba

1,064 steps to the top of the Kingdom of the Netherlands

Mount Scenery is a staircase through cloud forest to the highest point of the whole Dutch kingdom, on an island with no beach and no harbour.

US$3 trail fee; guides US$25–35

Leg 5

A hiker pulling up a steep muddy rainforest slope on a fixed rope.

Nevis

Nevis Peak, on ropes and roots

Four to five hours of hauling yourself up wet volcanic rock with fixed ropes. Muddy, steep, and one of the better views in the Leewards when the cloud lifts.

about US$60 pp guided

Leg 5

A kitesurfer carving across a shallow turquoise lagoon inside a reef, a bright kite high in a clear sky.

Union Island

Learn to kitesurf where we are already anchored

JT Pro Center sits on Clifton's kite beach with its own safety boat. Mid-November to July is the wind season, so we are well inside it — and the anchorage is the spot, which is not true anywhere else on this list.

from US$195 a half-day

Leg 1

A hydrophone going over the side of a small boat into deep water off a green volcanic coast.

Dominica

Listen for sperm whales on a hydrophone

Dive Dominica out of Roseau: three hours, they drop a hydrophone, find the clicks, and take you to them. Sightings peak November to March and hold through April at close to the same rate.

US$69 pp, or about US$690 for the boat Boat observation only. Getting in the water is permit-only and sells as a multi-day expedition — see the whale section above.

Leg 3

Sunken boat sculptures on pale sand in shallow turquoise water, a snorkeler at the surface above.

Grenada & Carriacou

Two underwater sculpture parks

Molière, the first one anybody built, 75 figures in 5–8 m of water since 2006, plus 27 added in 2023. And off Carriacou, A World Adrift — thirty sunken boat sculptures set down in 2024, shallow enough to snorkel.

US$7 park entry plus US$10 pp a day

Legs 1–2

A classic twelve-metre racing yacht heeling under full sail with crew hiking out along the rail.

Sint Maarten

Race an actual America's Cup twelve-metre

Stars & Stripes and Canada II still race out of Philipsburg with paying crew grinding the winches. Two and a half hours, and you are working, not watching.

US$99 adults

Legs 5–6

A diver’s torch lighting open coral polyps on a reef at night, black water all around.

Carriacou & Grenada

Dive it after dark

Meet at five, back by half eight. Lumbadive goes off Tyrrel Bay, Dive Grenada off Grand Anse. Everything on the reef changes shift at dusk.

US$75–120 pp

Legs 1–2

A sportfishing boat trolling a lure spread over deep blue ocean, a green island on the horizon.

Antigua

Fish the two months that matter

April opens the marlin season and is the peak of the yellowfin and blackfin tuna run, with mahi still about. Four-hour charters out of English Harbour and Jolly Harbour.

from about €520 a boat

Legs 4–5

A freediver descending head-down along a weighted line, the surface a bright disc far above.

Dominica

Freedive in Soufrière Bay

Blue Element run a training platform minutes off a protected bay where the bottom drops away fast. Two competitive world-class freedivers founded it; the water does not go below 26 °C and visibility is 20–30 m.

on request

Leg 3

A narrow-gauge double-deck railcar running through overgrown former cane fields towards a green volcano.

St Kitts

Ride the sugar railway

Eighteen miles of two-foot-six-inch gauge, laid between 1912 and 1926 to carry cane, now carrying double-deck railcars round the north of the island with a rum punch in your hand and the fields gone back to bush. Departures are timed to cruise-ship calls, so this one needs an email weeks ahead.

US$90–160 pp

Leg 5

An old wooden and iron water wheel turning at a working Caribbean rum distillery, cut cane stacked beside it.

Grenada

A distillery still driven by its water wheel

River Antoine crushes its cane with a working water wheel and boils in open coppers. You will see 1785 quoted for its founding — the estate's own trade body says only “17th century”, so take the date loosely and the machinery seriously. The overproof they make is above the strength an airline will carry, which tells you the rest.

small entry fee

Legs 1–2

Split cocoa pods and wet beans drying on a tray at a working plantation.

Grenada

Cocoa from the tree to the bar

Belmont Estate is a working plantation with lunch and a fermentary; the Grenada Chocolate Company is next door. Nutmeg processing stations on the same road north.

estate tour, small fee

Legs 1–2

A rum distillery under a large green volcano: copper still, stone chimney, barrels under a wooden roof.

Martinique

The only AOC rum in the world

Martinique's rhum agricole is made from cane juice, not molasses, and carries a controlled appellation like a wine. Depaz stands directly under Mont Pelée and is the one distillery on this route you can reach on foot from where the boat lies; Clément, Neisson and Saint James are a short drive.

free to walk round Depaz; €5 adds the château and a tasting The cane harvest runs February to June, so we are there mid-harvest — mills crushing, stills running, fermentation going. Rhum agricole can only be made in these four months, and this is the only time of year you can watch it happen.

Legs 1, 3, 6

Half-finished hand-carved model sailing boats on a workbench in an open harbourside workshop.

Bequia

Watch model boats being built by hand

Bequia builds real boats and miniature ones, and the workshops in Port Elizabeth will make you one. The Heritage Museum at St Hillary covers the boat-building and the whaling.

museum EC$25 Museum opens Monday, Wednesday and Friday, 10:00–13:00 only.

Leg 1

A frigate bird colony in low mangrove, several males with inflated scarlet throat pouches.

Barbuda

The frigate bird colony at Codrington Lagoon

One of the largest colonies in the world, reachable only by a local boat through the lagoon. The males inflate a scarlet throat pouch the size of a football. The season runs September to April, and we get there in its last fortnight.

local boat, negotiated

Leg 5

An eighteenth-century stone fortress with cannon on a volcanic outcrop high above the sea.

St Kitts

Brimstone Hill

A British fortress built by enslaved Africans over a century of work, on a volcanic outcrop nine hundred feet above the sea. UNESCO listed, and the walls are largely intact.

entry fee

Leg 5

A beach barbecue at dusk: grills and trestle tables under palms, dinghies pulled up on the sand.

Dominica

The PAYS beach barbecue at Portsmouth

The boat boys' association throws it on the beach every Wednesday and Sunday at seven — food, rum punch included, and the anchorage walks ashore together. It runs all year, and six days at Dominica means we catch at least one.

US$25 all in

Leg 3

A hilltop fort terrace above a harbour full of anchored yachts at sunset, a band playing on the ramparts.

Antigua

A whole week of English Harbour

The dockyard has something on most nights and all of it is within a mile of the mooring: Clarence House on Wednesday, Reggae Heights on Thursday, Rum in the Ruins and Seafood Friday on the Friday, and on Sunday the Shirley Heights party on the ramparts — steel band, then brass, with the whole UNESCO dockyard laid out below you. All of it runs year round, week in and week out.

Shirley Heights about US$10

Legs 4–5

A catamaran at anchor under a full moon, the moon path across the water and a dark island behind.

Everywhere

A full moon and a dark of the moon

The moon is new on Tuesday 6 April and full on Wednesday 21 April 2027. On a boat with no light pollution in any direction those are two genuinely different kinds of night — one for the stars, one for reading on deck at midnight.

free

Legs 3 and 5

A rider on a long zipline cable running down a steep green mountainside above a wide lagoon.

Sint Maarten

Drop 1,050 feet down a mountainside on a wire

The Flying Dutchman runs 2,800 feet of cable down Sentry Hill with a thousand-foot vertical drop. Fifteen minutes from the Simpson Bay dinghy dock.

US$109; the park runs 11:00–16:00 Billed by its operator as the steepest in the world. Guinness keeps no such category, so treat it as their claim, not a record.

Legs 5–6

A canopy zipline platform on an old cocoa plantation, the sharp forested cone of a volcanic peak behind.

Saint Lucia

Zipline over a working plantation under Petit Piton

Morne Coubaril is an eighteenth-century estate directly beneath the Piton, still growing cocoa and cassava. An hour on the canopy lines, ten minutes by taxi from the Soufrière mooring.

US$75

Leg 2

A rope suspension bridge high in the rainforest canopy, a walker halfway across.

Antigua

Antigua's rainforest canopy

Six to thirteen lines and a set of suspension bridges through the canopy on Fig Tree Drive, twenty minutes from Falmouth Harbour.

from US$74; Mon–Sat, 08:30–15:30

Legs 4–5

Shallow Amerindian rock carvings on the pale wall of a limestone cave, daylight coming in from the entrance.

Barbuda

Petroglyphs in a cave, and a sinkhole with a forest in it

Indian Cave at Two Foot Bay holds the only Amerindian rock carvings left on Barbuda. Darby Sink Hole is three hundred feet across with its own pocket of rainforest growing on the floor. Neither has a ticket office; both need a guide from Codrington.

guide negotiated locally

Leg 5

A restored stone fort above a harbour with a line of old cannon on the rampart and a tall ship anchored below.

Sint Eustatius

The first salute

On 16 November 1776 the guns of Fort Oranje answered a salute from the American brig Andrew Doria — the first time any foreign power acknowledged the United States existed. Roosevelt's 1939 plaque is still on the wall, a short walk up from the dinghy dock, on an island almost no yacht stops at.

free

Leg 5

Horses swimming chest-deep in clear turquoise water with their riders still on them.

Nevis & Anguilla

Ride a horse into the sea

Nevis Equestrian Centre does ninety minutes, Seaside Stables at Cove Bay on Anguilla does an hour. Both finish the same way, with the horses swimming and you still on them.

US$75–80

Legs 5–6

A small open tourist train running on narrow tracks through tall sugar cane towards a green mountain.

Martinique

A plantation train that still runs

The Petit Train des Plantations at Saint James in Sainte-Marie runs six days a week through the cane. It also quietly undoes the slogan on St Kitts's railway: this one is in the West Indies too, and it is working.

€8

Legs 1, 3, 6

There is no tourist submarine anywhere on this route. Atlantis runs Barbados, Cozumel and Aruba and nothing in the islands we visit; the old operators here have closed. And there is no bioluminescent bay of the sort Puerto Rico and Jamaica are known for — you get occasional plankton in a wake, which is lovely, and is not the same thing.

There is also no scheduled seaplane and no hot air balloon, and I could find only one skydiving drop zone on the whole chain. Several operators still advertised by the big booking sites shut down after Hurricane Irma in 2017 and never reopened; I checked, and they are not on this list.

What people actually carry home

A bottle of agricole rum and a glass on a wooden table, sugar cane and a volcano behind.

Rhum agricoleMartinique. Cane juice, not molasses, and the only appellation-controlled rum there is.

Whole nutmegs in red mace spilling from a burlap sack beside cocoa beans and a block of cocoa.

Nutmeg and cocoaGrenada. Bought at the processing station rather than the airport, for a fraction of it.

A finished hand-carved model schooner on a workbench, the harbour through the workshop door.

A model boatBequia. Built by hand in Port Elizabeth, and they will make one to order.

Hands working drawn-thread lace on white linen, finished pieces folded beside them.

Saba laceSaba. Drawn-thread work the island has been doing since the 1870s.

Customs note, learned the hard way by other people: Grenada's River Antoine overproof is above the strength airlines will carry. Drink it there.

Life aboard

Food, internet, and not much of a schedule

A single plated main course on the cockpit table: a thick grilled steak sliced open, charred courgette, pepper and spring onion, a bowl of salad and a glass of red wine, the anchorage just behind.

There is a cook aboard for all five weeks

This is not a self-catering charter where the guests take turns at the stove. Three meals a day are included, plus drinking water: breakfast in the cockpit, lunch usually at anchor, dinner aboard or ashore depending on where we are.

Half of this route is France — Martinique, Guadeloupe, Les Saintes, St Barth — which means real supermarkets, proper cheese, charcuterie and wine at French prices, in the Caribbean. The other half is markets: Dominica's produce, Grenadian spice, fish bought off the boat that caught it, lobster in the Tobago Cays. Six restocks, one per handover port, so the food changes as the islands do rather than being one supermarket run stretched over five weeks.

There is a grill on the stern rail, and meat gets its share of it: steaks, chops and chicken, not only fish. Evenings at anchor mostly end the same way — the grill going and a hookah in the cockpit.

A bakery counter in Les Saintes: baguettes upright in a basket, pastries under glass, a handwritten price card.

Les Saintes, on a Tuesday morning on leg 3.

Alcohol and soft drinks are not included: everyone buys their own ashore. Dietary requirements are handled if you tell me at booking.

An open laptop on the cockpit table with a game on the screen and a gaming mouse beside it, the sea directly behind.

You can work from this boat

Starlink Maritime is aboard for the whole trip: unlimited data within 12 nautical miles of shore, which is where the boat is almost all of the time. People who cannot take five weeks of leave can take five weeks of laptop.

The one exception is the leg 6 offshore passage, where coverage runs on a lower-priority mode. Treat those days as email, not calls.

The shape of a day

There is not much of a schedule, which is the point. We sail in the morning while the breeze is steady, arrive somewhere in the early afternoon, swim, go ashore or don't, eat in the cockpit and sleep at anchor. Two to four hours of actual sailing on most days, and nobody is required to do anything with a rope.

About seasickness

Catamarans do not heel; spring trade-wind sailing in the lee of the islands is flat water — lighter and steadier than the winter, and the sea a good 25 cm smaller; and there is exactly one genuinely open passage, leg 6, and it comes at the very end.

Two honest remarks from me

I am not much of a drinker, and this is not shaping up as a drinking trip. Adventures, a hookah in the cockpit, fishing off the stern, good stories and a good mood: all of that will have everyone's full support.

And it works in digital-nomad mode. Starlink is aboard, calls and a working day are fine, and a catamaran has enough tables and corners for everyone to sit properly and even get a bit of privacy. Paddleboards, the hookah, the grill, the fishing gear: all of it will be there.

People lying on the trampoline netting at the bow, the sea rushing past below the mesh.

Someone mid-air off the side deck into deep clear water, another person watching from the transom.

Sunset from the cockpit at anchor, two people sitting on the coachroof with drinks, backs to the camera.

The card

Fifteen jurisdictions, six countries, 19 regions, 35 days

Three different ways of counting, because different people aboard care about different ones. If you count UN countries, the southern half is where your value sits. If you count NomadMania regions, the north is.

Tap a tile to stamp it. Fifteen tiles, six of them UN member states, six Saturdays, one boat.

The argument, in one number

Nowhere else on earth packs sovereign borders this tightly. Between Antigua and Anguilla — a stretch you can cross in four days of two-hour hops — there are nine separate jurisdictions in 78 nautical miles: Antigua & Barbuda, St Kitts, Nevis, Sint Eustatius, Saba, Saint-Barthélemy, Sint Maarten, Saint-Martin and Anguilla.

Stops per 100 nautical miles, by stretch
Stretch	Distance	Density
Northern Leewards — Antigua → Anguilla	78 nm	11.5
Mid-chain — Martinique → Antigua	150 nm	2.0
Windwards & south — Martinique → Grenada	200 nm	2.0

Four of these countries are worth two regions each

Antigua & Barbuda, St Kitts & Nevis, St Vincent & the Grenadines and Grenada each split into two NomadMania regions — eight of the nineteen — and in three cases the second is a trivially short hop. Nevis is 10 nm from St Kitts. Carriacou is 12 nm from Union Island. Bequia is a normal Grenadines stop. Barbuda is 32 nm north of Antigua. The route deliberately picks up all four.

Worth knowing the other way round: Guadeloupe and all its dependencies — Les Saintes, Marie-Galante, La Désirade — are a single region however many of them you touch. Lovely islands; they just do not multiply.

How the numbers were checked

Every region name and ID on this page was pulled directly from the NomadMania API and checked against a real profile to confirm which are genuinely new. That is how we know Guadeloupe's dependencies are one region rather than four, and that Nevis and Carriacou score separately from their parent islands. Those two facts changed the route.

The tool that does it is wanderfill, an open-source project for working with NomadMania programmatically — region lookups, visit tracking, bulk operations the web interface cannot do: github.com/faeton/wanderfill.

6UN member states

15jurisdictions, flags and customs desks

19NomadMania regions

42days aboard

7regions on leg 5 alone

11.5stops per 100 nm in the Northern Leewards

The 15 jurisdictions and their NomadMania region IDs
Jurisdiction	Status	Reg.	ID
🇻🇨 St Vincent & the Grenadines	UN	2	1089 · 1090
🇬🇩 Grenada	UN	2	1074 · 1075
🇱🇨 Saint Lucia	UN	1	1088
🇩🇲 Dominica	UN	1	1067
🇦🇬 Antigua & Barbuda	UN	2	1058 · 1059
🇰🇳 St Kitts & Nevis	UN	2	1086 · 1087
🇲🇶 Martinique	France	1	1071
🇬🇵 Guadeloupe + Les Saintes	France	1	1070
🇲🇸 Montserrat	UK	1	1096
🇧🇶 Sint Eustatius	Netherlands	1	1084
🇧🇶 Saba	Netherlands	1	1083
🇧🇱 Saint-Barthélemy	France	1	1073
🇸🇽 Sint Maarten	Netherlands	1	1085
🇲🇫 Saint-Martin	France	1	1072
🇦🇮 Anguilla	UK	1	1093
Total	6 UN member states	19

Saba and Sint Eustatius share the 🇧🇶 Caribbean Netherlands flag but are separate regions. Region IDs and counts from the NomadMania API, checked August 2026.

Practicalities

Visas, flights, and the parts you would ask about anyway

Fifteen jurisdictions means fifteen sets of paperwork, and the boat clears in as a single vessel on one crew list — so everyone's documents need to work everywhere. That is why this section is long rather than folded away.

Every jurisdiction, two passports

Two positions per place, because those are the two passports the people I am asking actually hold. On a phone each jurisdiction is a card carrying both; on a wider screen they are two columns.

On an EU, EEA or Swiss passport, fourteen of the fifteen need nothing at all.The exception is one eTA for St Kitts & Nevis: an online form, US$17, approved in about a day.

On a Ukrainian biometric passport, eleven of the fifteen are visa-free.Two are online forms, one is satisfied by a US, UK or Canadian visa you may already hold, and one is a real consular visa — Saint Lucia, by post, started in October.

Nothing to do before you flyOne thing to do, and it is doable

Entry position for each of the fifteen jurisdictions, for a Ukrainian biometric passport and for an EU, EEA or Swiss passport
Where	Ukrainian biometric	EU / EEA / Swiss
Martinique France · legs 1, 3, 6	Visa-free 90 days in 180. Overseas France sits outside Schengen and Ukraine is exempt there in its own right.	EU territory. An outermost region: free movement, national ID card or passport. Not in Schengen, so there is still a border check.
St Vincent & the Grenadines UN · legs 1–2	Visa-free 3 months.	Visa-free. The EU treaty floor is 90 days in 180; the national list gives most EU passports 6 months. No online form — a paper card on arrival. Irish passports are listed separately: check your own line.
Grenada UN · legs 1–2	Visa-free 3 months.	Visa-free 3 months. Grenada launched an electronic E/D card at edcard.gov.gd in March 2026 — free, filled in before arrival.
Saint Lucia UN · leg 2	Consular visa. The one piece of paperwork on this route with a lead time. By post to the High Commission in London, no personal appearance, about a week. Start it in December.	Visa-free 90 days in 180 under the EU–Saint Lucia short-stay waiver of 2015. Nothing to apply for. Irish passports sit on a separate line — six weeks — so check yours.
Dominica UN · leg 3	Visa-free 90 days.	Visa-free. 90 days in 180 by treaty, 6 months on the national list. Online immigration and customs form at edcard.dominica.gov.dm.
Guadeloupe + Les Saintes France · legs 3–4	Visa-free 90 days in 180.	EU territory. Outermost region, same as Martinique: ID card or passport, border check on arrival.
Montserrat UK · leg 4	eVisa. immigration.ms, US$50, approved in about 24 hours, valid 12 months, multiple entry, credit card only. No US or UK substitution here.	Visa-free up to 6 months. The immigration.ms eVisa exists for passports that are not exempt, and an EU one is.
Antigua & Barbuda UN · legs 4–5	Visa-free 180 days.	Visa-free 180 days — but an electronic ED card at ArriveAntigua.com is now required of everyone, at least 24 hours before arrival. Paper cards are no longer accepted.
St Kitts & Nevis UN · leg 5	eTA. An online form at knatravelform.kn, not a consulate appointment. Doable a few days ahead from the anchorage.	eTA as well. Visa-free 90 days, but since 26 May 2025 every foreign traveller needs the eTA — knatravelform.kn, US$17, single entry, valid 90 days, approved in about a day. This is the one place the EU column is not easier than the Ukrainian one.
Sint Eustatius Netherlands · leg 5	Visa-free.	Visa-free 90 days. The Caribbean Netherlands run their own visa policy — a Schengen visa is not what is being checked here, and an EU passport does not need one.
Saba Netherlands · leg 5	Visa-free.	Visa-free 90 days, same policy as Statia.
Saint-Barthélemy France · leg 5	Visa-free 90 days in 180.	Visa-free. St Barth left outermost-region status on 1 January 2012 and is now an associated overseas country, but EU and Schengen nationals still enter on an ID card or passport with no stated limit.
Sint Maarten Netherlands · legs 5–6	Visa-free.	Visa-free 90 days, and a free digital ED card at entry.sx that explicitly covers yacht arrivals as well as flights. Fill it in before we clear in.
Saint-Martin France · leg 6	Visa-free 90 days in 180.	EU territory. Saint-Martin is still an outermost region even though St Barth is not — free movement, ID card or passport.
Anguilla UK · leg 6	A US, UK or Canadian visa substitutes. Ukraine is on Anguilla's visa list, but a valid US, UK or Canadian visa or green card stands in for one. Send me the expiry date.	Visa-free 3 months. No third-country visa needed.

Researched in September 2026; every position gets confirmed before departure, and where I could not pin one down the honest answer is to ask the consulate rather than guess.

On a Ukrainian biometric passport

Eleven of fifteen need nothing at all. Every French island and every Dutch one is visa-free for 90 days, and so are Dominica, Antigua & Barbuda, St Vincent & the Grenadines and Grenada, on 90-day-to-six-month stays.

Two forms, both online. St Kitts & Nevis needs an eTA. Montserrat needs an actual visa, and unlike Anguilla there is no substitution for a US or UK one — but it is an eVisa: immigration.ms, US$50, about 24 hours, valid 12 months, multiple entry, credit card only. Both can be done a few days ahead from the anchorage, and we will send the links and do them together as a crew.

Saint Lucia is the one with a lead time — start it in December. It is the single island on this route that asks Ukrainian citizens for a proper consular visa. Not difficult, not expensive, but it cannot be done last-minute: applications go by post to the Saint Lucia High Commission in London, 1 Collingham Gardens, SW5 0HW, you do not have to appear in person, five documents, about a week of processing. It is one UN country and one region. If you would rather not bother, say so early — we can sail past St Lucia without clearing in, and it costs the trip one stop rather than a problem at the dock.

Anguilla wants a US, UK or Canadian visa. Most people joining already hold at least one. If nobody does, Anguilla is the last stop on the chain and the easiest to drop; it costs one region and nothing else. Either way, tell me at booking and send the expiry date — a visa that lapses mid-trip is the same as not having one.

On an EU, EEA or Swiss passport

Shorter, but not empty. Nothing on this route needs a consulate, and no fee is over US$17 — but five jurisdictions now want something filled in online before you arrive, and one of them charges for it.

St Kitts & Nevis — eTA, US$17, knatravelform.kn. The only paid item in this column.
Antigua & Barbuda — electronic ED card, ArriveAntigua.com, free, at least 24 hours ahead.
Sint Maarten — digital ED card, entry.sx, free, and it covers arrival by yacht.
Grenada and Dominica — electronic arrival cards at edcard.gov.gd and edcard.dominica.gov.dm, free.

The French islands are the simple ones: Martinique, Guadeloupe and Saint-Martin are EU outermost regions, so an EU passport or national identity card is the whole answer. They are not in Schengen, so expect a border check anyway. Saint-Barthélemy became an associated overseas country in 2012 and is a shade more complicated on paper, but in practice it takes the same documents.

Vessel clearance is separate from your passport and it is the skipper's job, not yours — most of these islands accept an advance crew list through SailClear, which is why fifteen sets of formalities do not eat fifteen mornings. Clearance fees for all fifteen are already in the price.

Everyone, regardless of passport

Passport valid at least six months beyond 1 May 2027, with clear pages — you will collect a lot of stamps.
Travel and medical insurance that covers sailing. Not optional. Read the policy for an exclusion on being offshore; several standard ones have it.
A soft bag, not a suitcase. There is nowhere on a boat to put a hard case. Swim things, a light layer for night watches, reef-safe sunscreen, and less than you think.
Changeovers are Saturday mornings. Arrive the night before if you can — a delayed connection on the Saturday is the one thing that is genuinely hard to fix.

An open passport spread, both pages covered edge to edge with overlapping tropical entry and exit stamps in blue, green, purple and red ink.

Fifteen jurisdictions, and the boat clears in and out of every one of them. Bring pages.

Fly in, fly out, and how hard it is to get there
Week	In	Out	Connections
1	FDF	GND	FDF direct from Paris; GND needs a connection
2	GND	FDF	GND needs a connection; FDF direct from Paris
3	FDF	PTP	Both direct from Paris
4	PTP	ANU	PTP direct from Paris; ANU direct from London
5	ANU	SXM	ANU direct from London; SXM direct from Paris or Amsterdam
6	SXM	FDF	SXM direct from Paris or Amsterdam; FDF direct from Paris

FDF Fort-de-France, Martinique · GND Maurice Bishop, Grenada · PTP Pointe-à-Pitre, Guadeloupe · ANU V.C. Bird, Antigua · SXM Princess Juliana, Sint Maarten. For the whole 35 days: into FDF on 26 March or earlier, out of FDF from 1 May; connections via Paris, Miami or Panama City.

If you are bringing a drone, read this before you pack it

Drone law is the one area on this route where fifteen jurisdictions genuinely do not agree with each other. Two of them have no lawful category for a drone at all, one can take the aircraft off you at the border, and two free forms filed from home clear five of the rest.

A small folding camera drone on the deck of a catamaran, its controller and a phone beside it.

What it takes to fly a camera drone, jurisdiction by jurisdiction
Where	Before you fly
Martinique · Guadeloupe · Saint-Martin · Saint-BarthélemyFrance	AlphaTango operator registration, free, online, done before you leave. A separate préfecture declaration for anything over a populated area — allow five working days, and up to a month for Saint-Martin and St Barth. The core zone of the Guadeloupe national park is a flat no, with a fine attached.
St Vincent & the GrenadinesBequia, Mustique, Tobago Cays	Two forms, one to the NTRC and one to Civil Aviation. Both are free and both can be emailed from abroad, and they give you a 90-day temporary registration. The easiest paperwork on the route — do it in January.
Grenadaand Carriacou	Written permission from the Royal Grenada Police Force, applied for in advance with your passport and the aircraft's serial number. Reported to cost about EC$10.
Antigua & Barbudathe one to worry about	Registration and an Operator Certificate, and the certificate needs an Antiguan police record of good character. Under the 2019 regulations an imported drone goes into a customs-controlled area on arrival and is released on a declaration or on production of that certificate. Declare it, and be prepared to leave it in bond for the week.
St Kitts & Nevis	Customs registration on arrival plus permission from the airport authority.
Saint Lucia	Written permission from the Civil Aviation Department. Allow two to three weeks.
Sint Maarten	No permit for recreational flying outside the published no-fly zones — but the approach to Princess Juliana, Maho beach included, is one of them. That is the shot everybody wants and it is the one that is named.
Anguilla · MontserratUK territories	Nothing to file for basic line-of-sight flying under 400 g. Anything beyond that needs ASSI permission, and they want 28 days. Montserrat has a mapped no-fly box at the airport, and the volcano is not a place to try it.
Saba · Sint Eustatiusleave it in the cabin	There is no lawful category for a drone here and nobody to ask for permission. Not a hard permit — an absent one. Two of the most photogenic islands on the whole route, and you will be shooting them from the deck like everyone else.
Dominica	I could not establish the rule from an official source, and the aggregator sites are quoting Antigua's numbers on Dominica's page. Treat it as unknown and ask on arrival rather than guessing.

Four things that catch people out

Sub-250 g saves you nowhere on this route. France registers any camera drone whatever it weighs, the UK territories' threshold is 400 g rather than 250, and Antigua classifies by whether the aircraft can climb above 100 feet — which puts every Mini in the strict tier.
Two free jobs at home clear five jurisdictions. AlphaTango covers the four French islands; the SVG pair covers the Grenadines. Both are free, both are email, both take an evening.
The 300-metre rule around whales applies in the air. The French prefectoral order names drones explicitly. In the season we are sailing, that is not a hypothetical.
Mustique is privately administered. Nothing bans a drone outright, but its terms forbid publishing photographs featuring other people — and the other people are rather the point of Mustique.

Same footing as the visa table: this is a plan, not aviation advice, and every position gets confirmed before departure. If you are bringing an aircraft, tell me in the autumn and we will do the paperwork together — most of it has to be filed before anyone leaves home.

Getting to Le Marin

A traveller with a duffel bag walking out of a small tropical airport terminal into palms and warm afternoon light, seen from behind.

Fort-de-France, and then forty-five minutes south. This is the whole arrival.

The boat is in Le Marin, at the south-east tip of Martinique. You fly into Fort-de-France (FDF, Aimé Césaire airport), and Le Marin is about 45 minutes from there by taxi or rental car. Martinique is France: for an EU passport it is a domestic arrival, with no visa, euros, and the usual EU roaming.

When. Boarding is Saturday 27 March 2027 in the morning. Fly in on Thursday 25 or Friday 26 March; I will be in Le Marin from the Wednesday. Going home, fly out of FDF on Saturday 1 May or the Sunday. Flights to Europe leave in the evening and land the next morning.

The gateway is Paris. Air France, Air Caraïbes and Corsair fly nonstop from Paris to Fort-de-France every day, about eight and a half hours. Check which Paris airport your connection lands at: Orly and Charles de Gaulle are both used, and a transfer between them takes an hour and a half.

From Warsaw: LOT or Air France to Paris, then the nonstop. About 13 hours door to door with one connection. The other way round is LOT to Miami and American Airlines from Miami to Fort-de-France, which runs in winter.
From Cyprus: Larnaca to Paris with Cyprus Airways or Transavia, then the nonstop. One connection, about 14 hours; Larnaca departures are mostly in the morning, so an overnight in Paris is the comfortable version.
From London: Either the short hop to Paris and the nonstop, or British Airways nonstop from Gatwick to Saint Lucia and the ferry from Castries to Fort-de-France with L'Express des Îles, about an hour and a half on the water and a fine way to arrive. Virgin Atlantic also flies to Saint Lucia.

Rough money: a Paris to Fort-de-France return in late March is usually €600–900 if booked by the autumn, plus the feeder flight. Easter Sunday is 28 March, so the outbound sits in the school-holiday band and the return, a month later, does not — book the outbound early. Send me your flight times once you have them and I will sort the transfer from the airport.

What is included, and what is not

In the price

The boat
The skipper
The cook
All food and drinking water
Fuel
Moorings
Clearance fees for all fifteen jurisdictions
Masks, snorkels and fins, and the dinghy that gets you to the reef
The grill on the stern rail, the paddleboards, the hookah and the fishing gear

Not in the price

Flights
Alcohol and soft drinks — everyone buys their own ashore
Diving with local operators
Your visas
Travel insurance
What you do ashore

Do I need to know how to sail

No. There is a professional skipper aboard and nobody is required to do anything with a rope. If you do want to steer, navigate or learn to trim a sail, legs 2 and 6 are the ones where there is real sailing to be had. If you want to learn to helm, trim and navigate, there is no better way than five weeks of trade-wind sailing; if you would rather read in the shade and swim, that is equally fine.

The offer

What it costs

One number, then what it includes. Every price on this page is per person, two sharing a cabin — the whole cabin is twice it.

The whole trip first

All 35 days: €12,500 a person.

Two people sharing a cabin. The whole cabin, both berths, is €25,000.

This is the one I want to fill. Take a cabin and split it however you like: it is yours for the whole five weeks, and who is in it can change at any of the five handover ports. Keep it to yourself the whole way, hand it round a family, or run it as a company perk and send a different colleague out each time. One cabin, one price, and every handover is at an island with a proper airport, so the swaps are a flight, not a problem.

Two people sharing is the basis of every price on this page. One cabin to yourself is the €25,000, and it is yours.
Less than the whole trip? Tell me which legs and I will give you a number — but the whole trip goes first, and I would rather sell it that way.

In the price

Boat, skipper, cook
All food and water
Fuel and moorings
Clearance fees for all fifteen jurisdictions

Not in the price

Flights
Alcohol
Diving
Your visas
What you do ashore

No booking engine and no card details on this page. These are the numbers I am working from as a cost share among the people aboard; write to me and we will talk.

€12,500 a person, all 35 daysa whole cabin is €25,000

Ask about a cabin