7-Night Leeward Islands Yacht Charter Itinerary from St Maarten
St Martin, Anguilla and St Barts
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French, Dutch, British and the most glamorous harbour in the Caribbean, all within a morning's sail of each other
Three Islands, Three Flavours
A 7-night crewed yacht charter that starts and ends in St Maarten and takes in three islands that could not be more different. St Martin itself is the smallest island in the world shared by two nations, French on the north side and Dutch on the south, with 37 beaches, a lagoon full of yachts and the best restaurants in the Leewards. Anguilla, a short hop north, is British, flat, quiet and ringed with the whitest sand in the Caribbean. And St Barts, to the south-east, is the Caribbean’s answer to St-Tropez: a French island of red roofs and designer boutiques whose harbour, Gustavia, is the hub of the Caribbean superyacht season and the place the world’s largest yachts gather for New Year’s Eve, which is why berths and tables there are booked many months ahead. This is the natural next step for anyone who has done the British Virgin Islands and wants something new: the same trade winds and warm water, a few more miles between the islands, so more time under way with the sails up or the engines humming, and three flags, three cuisines and three kinds of beach in one week. It works equally well on a sailing yacht, a catamaran or a motor yacht; the crew handle the sailing, the meals, the moorings and the clearances, and shape every day around what you feel like doing.
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St Martin, Anguilla and St Barts Yacht Charter Itinerary
Total Distance: ~110nm Cruising Time: ~13 Hours
Route: Simpson Bay — Grand Case — Road Bay and Sandy Island (Anguilla) — Prickly Pear and Shoal Bay — Tintamarre and Pinel — Île Fourchue — Anse de Colombier — Gustavia — Simpson Bay
Vessel: Crewed Sailing Yacht, Catamaran or Motor Yacht
Saturday — Welcome aboard
Day 1: St Maarten to Grand Case | ~12nm
Boarding in St Maarten, usually in Simpson Bay on the Dutch side, ten minutes from Princess Juliana airport, where the big jets come in low over Maho Beach and the lagoon behind it holds more yachts than anywhere else in the Leewards. The crew meet you with a cold drink and a cooler of ideas, the luggage goes below, and the first leg is a gentle one: out through the bridge, round the western tip of the island past Cupecoy and Baie Longue, and along the French coast to Grand Case. The bay is calm, the village is one long street of Creole houses, and the street is the gourmet capital of the Caribbean, with a dozen French restaurants and a row of lolos, the open-air barbecue stands where ribs, lobster and johnny cakes come off the grill for a few dollars. First dinner ashore or on deck, and the first night at anchor with the lights of the village along the beach.
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Sunday — Sandy Island
Day 2: Grand Case to Anguilla | ~15nm
The crossing to Anguilla is the first proper passage of the week, two hours north across the Anguilla Channel with the trade wind on the beam, which on a sailing yacht is as good as it gets. The yacht clears in at Road Bay, Anguilla’s harbour, a crescent of sand with a handful of beach bars and a fleet of wooden racing boats pulled up on the beach; the crew take the passports ashore while you swim. Then it is a mile out to Sandy Island, which is exactly what it says: a spit of white sand with a few palms and a beach bar, in water so clear the anchor chain throws a shadow on the bottom. The afternoon is for snorkelling the reef, the paddleboards, and lobster at the bar’s long table with your feet in the sand. Night back in Road Bay, where the sunsets are the best in the Leewards.
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Monday — The whitest sand in the Caribbean
Day 3: Prickly Pear and Shoal Bay | ~12nm
A short run north-west to the Prickly Pear Cays, two uninhabited islets ringed by reef, with a lagoon between them where the snorkelling runs along a coral wall alive with parrotfish and rays; the beach on Prickly Pear East has a bar that opens when the boats arrive. After lunch the yacht works back along Anguilla’s north coast to Shoal Bay East, two miles of blinding white sand that regularly tops the lists of the world’s best beaches, with warm shallows for the children and a reef a short swim out for everyone else. Dinner can be on board or at one of the beach restaurants, where grilled crayfish and rum punch are the order of the evening. Night at anchor off Shoal Bay or back in Road Bay, depending on the swell.
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Tuesday — The nature reserve
Day 4: Anguilla to Tintamarre and Pinel | ~18nm
Back across the channel, clearing out of Anguilla in the morning, and round the north-east corner of St Martin into the marine reserve that protects the whole of this coast. Tintamarre is a flat, uninhabited island a mile offshore with a beach of pale sand on its western side, turtles grazing on the seagrass off it and the remains of a 1940s airstrip in the scrub behind; the yacht anchors for lunch and the water toys. In the afternoon she moves into the shelter of Pinel Island, a small green island off Cul-de-Sac with two beach restaurants, a trail round the back where the iguanas sunbathe, and a sand bar you can paddle to. Orient Bay, the long resort beach of the French side, is the next bay south for anyone who wants a sunset drink with more people around. Night at anchor behind Pinel.
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Wednesday — The passage to St Barts
Day 5: Pinel to Île Fourchue and Anse de Colombier | ~22nm
The longest and best sail of the week, two to three hours south-east across the open channel to St Barts, with the island rising ahead and the trade wind free. The first stop is Île Fourchue, a horseshoe of bare brown hills halfway across that encloses a bay of deep blue water, with nothing ashore but goats and a walk to the ridge for the view back to St Martin; the snorkelling along the rocky sides of the bay is the best of the week. From there it is a short run to the north-west tip of St Barts and Anse de Colombier, a bay with a white beach reached only by sea or by a footpath from the hills, which is why it is the quietest beach on an island famous for its beaches. Night on a mooring in Colombier, with the lights of Gustavia just round the headland.
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Thursday — The harbour of the famous
Day 6: Colombier to Gustavia | ~5nm
Into Gustavia, the capital of St Barts, a horseshoe harbour of red-roofed houses with the largest yachts in the world stern-to on its quays. The town was Swedish for a century, which explains the name and the neat grid of streets, and it is now the most elegant few blocks in the Caribbean: Hermès, Cartier and Louis Vuitton beside the fishing boats, cafés on the quay, and the Wall House museum for the history. A rented Mini Moke is the island way to see the rest: the lighthouse, the airstrip at St Jean where the planes drop over the hill onto one of the shortest runways in the world, the beaches of Saline and Gouverneur with no buildings behind them, and lunch at a beach restaurant at Flamands or St Jean. Dinner ashore in Gustavia, where the restaurants are French and the tables, in season, are booked well ahead. Night in the harbour or at anchor in the outer bay.
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Friday — Shell Beach and the sail home
Day 7: St Barts to St Maarten | ~20nm
A last morning in St Barts: a swim at Shell Beach, a five-minute walk from the harbour and carpeted, as the name says, with shells, or a run round to Grande Saline for the surf. Then the sail home, two to three hours downwind to St Maarten with the spinnaker up if the yacht carries one, which is the leg the sailors on board will remember. The afternoon is for Philipsburg, the Dutch capital, with its boardwalk along Great Bay and the duty-free shops of Front Street, or for a last quiet anchorage on the south coast at Baie Longue. The farewell dinner is on board, in the lagoon or at anchor off Simpson Bay, with the crew’s best dishes of the week.
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Saturday — Farewell
Day 8: St Maarten | Departure
Breakfast on board and disembarkation in Simpson Bay, at the time the yacht sets, with the airport ten minutes away. If the flights allow, keep a day: Marigot, the French capital, has a morning market on the waterfront and the ruins of Fort Louis above it, and the lolos of Grand Case are a 20-minute drive for one last lunch.
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Charter Costs
What a week like this costs
What the week costs depends on the yacht. Crewed catamarans in the Leewards are mostly all-inclusive, one weekly rate covering the yacht, crew, meals, bar and water toys; larger sailing and motor yachts quote a base rate plus an advance provisioning allowance for fuel, food, dockage and the rest. Rates are in US dollars or euros, St Barts carries its own port fees, and the Christmas and New Year weeks are priced above the rest of the season and booked a year ahead. The yachts below show real prices at every level.
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FAQ
BVI are best for the first time charteres and St Martin/ St Barts are a natural next step. The trade winds, the warm water and the easy anchorages are the same, but the islands are a little further apart, so there is more real sailing or cruising between them, and the three islands are three countries: French and Dutch St Martin, British Anguilla and French St Barts, each with its own food, beaches and feel. It suits sailing yachts, catamarans and motor yachts equally well.
No. Every itinerary is a plan, not a timetable, and it is always subject to the weather and to what you feel like doing. Most of these islands offer a lively harbour and a secluded bay within a few miles of each other, so the captain can stop at either, depending on the experience you are looking for that day.
For most of the season, a few months. For Christmas and New Year, a year or more: St Barts is the main hub for large-yacht New Year charters in the Caribbean, the harbour at Gustavia and the island’s restaurants fill well in advance, and the best yachts are reserved long before the summer.
December to April is the high season, with steady trade winds, little rain and the social calendar of St Barts in full swing; the St Barths Bucket regatta is in March. May, June and November are quieter with the same water temperature. Most yachts leave the area between August and October. The full season runs November through July.
The yacht clears in and out of each country on the way: Anguilla at Road Bay, St Barts at Gustavia, and St Martin on whichever side she returns to. The crew handle the paperwork; everyone aboard needs a valid passport.
Fly to Princess Juliana airport (SXM) on the Dutch side of St Maarten, which has direct flights from New York, Miami, Atlanta, Charlotte, Toronto, Paris and Amsterdam. Most yachts board in Simpson Bay, ten minutes from the terminal, or at Marigot or Anse Marcel on the French side, half an hour away.
St Martin, St Barts Yachts
Cleopatra
Caribbean Leewards, Caribbean Virgin Islands (BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (US/BVI)
54.00 ft ✦ 10 pax ✦ 5 cabins
$30,000 per week
+ expenses
ONE PLANET
Antarctica, W. Med – Spain/Balearics
77.10 ft ✦ 8 pax ✦ 4 cabins
€79,000 per week
+ expenses
My Marina
Caribbean Leewards, Caribbean Windwards, Caribbean Virgin Islands (US)
48.00 ft ✦ 4 pax ✦ 3 cabins
$9,000 per week
+ expenses
AVANTI
Caribbean Leewards, Caribbean Virgin Islands (BVI), Caribbean Windwards
74.50 ft ✦ 8 pax ✦ 4 cabins
$45,900 per week
+ expenses
Destiny Unbound
Caribbean Leewards, Caribbean Virgin Islands (BVI), Caribbean Virgin Islands (US), Caribbean Virgin Islands (US/BVI)
54.00 ft ✦ 12 pax ✦ 5 cabins
$30,000 per week
+ expenses
Our Pick 
VELA.
Caribbean Virgin Islands (BVI)
70.00 ft ✦ 8 pax ✦ 4 cabins
$79,000 per week
+ expenses
AQUA PANDA
Caribbean Leewards, Caribbean Windwards
38.22 ft ✦ 4 pax ✦ 2 cabins
$10,500 per week
+ expenses
EROS
USA – New England, USA – Florida East Coast, USA – Great Lakes, USA – South East, USA – North East, Caribbean Virgin Islands (US/BVI), Bahamas, Caribbean Leewards, Caribbean Windwards, Central America
115.00 ft ✦ 10 pax ✦ 4 cabins
$46,000 per week
+ expenses
Songbird
Caribbean Leewards, Caribbean Virgin Islands (US/BVI), Caribbean Windwards
57.00 ft ✦ 10 pax ✦ 5 cabins
$31,000 per week
+ expenses
RISK & REWARD
Bahamas, Caribbean Leewards, Caribbean Virgin Islands (US/BVI)
120.00 ft ✦ 9 pax ✦ 4 cabins
$80,000 per week
+ expenses
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