Caribbean, Leeward Islands
Saint Martin is the hub of the northern Leewards: Marina Fort Louis in Marigot on the French side, Oyster Pond and Simpson Bay on the Dutch, with Anguilla 10 NM north, Saint-Barthélemy 15 NM south-east and Saba, Statia and Saint Kitts within a two-week loop; direct flights from Paris and the US and the best provisioning in the Leewards.

YACHT TYPES
Catamarans 40 to 50 ft dominate the fleets at Marigot and Oyster Pond; sailing yachts 40 to 50 ft; crewed catamarans and motor yachts from Simpson Bay on the Dutch side.
A typical week from Marigot
Saturday to Saturday. Saint-Barth first, upwind while the crew is fresh, then downwind to the Dutch side and Anguilla.
Day 1, Marigot to Tintamarre (9 NM). Round the north coast past Grand Case and Anse Marcel to the uninhabited island of Tintamarre: nature-reserve buoys, turtles, a beach and nobody living on it.
Day 2, to Saint-Barthélemy (14 NM). A close reach to Gustavia: the harbour buoys and stern-to berths cost what you expect; the anchorage at Anse de Colombier, 2 NM west, costs a park buoy and a walk to the beach.
Day 3, Colombier and Île Fourchue (4 NM). The horseshoe bay of Fourchue on buoys for the snorkelling, then back to Colombier or Gustavia for the evening.
Day 4, to Philipsburg or Simpson Bay (15 NM). Downwind to the Dutch side: the Simpson Bay lagoon through the bridge for the marinas and restaurants, or the anchorage off Philipsburg.
Day 5, to Anguilla, Road Bay (12 NM). Clear in at Sandy Ground: customs, immigration and the cruising permit, then the beach bars of Road Bay.
Day 6, Prickly Pear and Sandy Island (6 NM). The cays north-west of Anguilla on marine-park buoys; Sandy Island's one restaurant, Prickly Pear's reef.
Day 7, to Marigot (10 NM). Across the Anguilla channel and back to Fort Louis for the check-in, with time for the Marigot market.
Two weeks add Saba (28 NM from Simpson Bay, buoys only), Statia and Saint Kitts and Nevis (45 NM from Saint-Barth), a loop that comes back downwind. Both are in our Saint Martin itineraries.
Practical points for a Saint Martin charter
Licences and clearance
The French side asks for no licence in law but the operators want a sailing CV and, for bareboat, a recognised licence; a VHF certificate helps. Clearance is the week's paperwork: Saint-Martin (France, EU) and Sint Maarten (Netherlands) are two customs on one island, Saint-Barth is French but clears separately, Anguilla is British with customs, immigration and a cruising permit at Road Bay. Do not stop at Sandy Island or Prickly Pear before clearing in.
Wind and sea
Trade winds from the east to east-north-east, 15 to 25 knots from December to April, stronger in the Christmas winds of December and January; a north swell in winter makes the north-facing anchorages (Grand Case, Anguilla's north coast) roll for a few days at a time. Squalls pass in twenty minutes. The Saint-Barth leg is the upwind one; the rest of the week is reaching.
Moorings and fees
Gustavia's harbour buoys and berths are 60 to 200 euros a night for a catamaran in season and are booked ahead; the Colombier and Fourchue buoys carry a marine-reserve fee; Anguilla charges a cruising permit and marine-park fees per boat, a few hundred dollars for two days; the Simpson Bay bridge charges a fee to enter the lagoon; anchorages on the French side are free outside the reserve. Provisioning in Marigot and Simpson Bay is the best of the Leewards, with French supermarkets and a Saturday market.
Getting there
Princess Juliana airport (SXM) has direct flights from Paris, Amsterdam, New York and Miami and is 20 minutes from Marigot and Simpson Bay; Grand Case (SFG) takes the regional flights from Guadeloupe and Martinique. Taxis are fixed-price; a hire car is useful for the provisioning run.
Saint Martin or the BVI?
BVI for a first Caribbean charter: short legs, no clearance, buoys everywhere. Saint Martin for better food and flights, real trade-wind sailing and Saint-Barth and Anguilla, with more open water between stops.
Can we anchor at Saint-Barth in season?
Gustavia fills by noon in February; Colombier and Gros Îlets take the overflow on buoys. Book the harbour ahead for a Saturday night.
How much time do the formalities take?
Anguilla is an hour at Road Bay; Saint-Barth and Sint Maarten twenty minutes each with the forms prepared online. Plan the clearances for the mornings.
What does Seeksail need to advise us?
Dates, cabins, licence held, skipper or not, Saint-Barth or Saint Kitts as the goal, and we shortlist three yachts from Marigot, Oyster Pond or Simpson Bay with a recommendation.
PLAN WITH CONFIDENCE
More destination-specific guides are being prepared.
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