Three islands within a short sail of each other — Anguilla to the north, St Barths to the south, and Sint Maarten in the middle. Anguilla’s quiet, reef-fringed beaches, Sint Maarten’s lagoon, marinas, food spots and nightlife — split between two countries, French and Dutch — and St Barths’ quieter harbour and hillside villas make for three distinct legs of one trip.
Sailing conditions
The trades blow steadily across all three islands through the charter season, and Sint Maarten sits at the edge of the main hurricane belt, with Simpson Bay Lagoon giving sheltered water for most of the marinas on the Dutch side. Anguilla is low and flat with reefs around much of its coastline. The crossings between the three are short, well under 20 nautical miles. St Barths itself has few truly sheltered anchorages, so stops there are chosen as much for what the wind is doing that day as for what’s ashore.
On the water and on shore
Anguilla’s pace is set by its beaches — Shoal Bay East and Meads Bay are the two everyone asks for, Road Bay and Sandy Ground serve as the main anchorage and harbour town, and Prickly Pear and Scilly Cay are the usual lunch stops. On Sint Maarten, Marigot on the French side has a market and Fort Louis above it, Grand Case is the place to go ashore for dinner, and Philipsburg on the Dutch side is the main cruise port and shopping street. Orient Bay is the better-known beach, and Simpson Bay holds most of the island’s restaurants and nightlife. As for St Barths, Gustavia’s harbourfront doubles as a run of boutiques (Hermès and Louis Vuitton among them), worth a stop for shopping as much as for the harbour; Corossol is still a working fishing village, and Anse de Grand Saline is one of the quieter beaches. Anse de Colombier and Île Fourchue, both inside St Barths’ marine reserve, are the two anchorages worth building a day around; moorings protect the reef.
Chartering Anguilla, Sint Maarten and St Barths with LV
Anguilla, Sint Maarten and St Barths sit close together but cross three different paces, so we plan the route around that rather than just plotting a straight line — how much time to give Anguilla’s beaches, Sint Maarten’s lagoon and marinas, and St Barths’ quieter anchorages — so the itinerary, yacht and crew suit the trip you actually want. Itineraries also don’t need to cover all three Islands, so we plan around your timings and how much you want to visit.
