St Martin Itineraries: Day Charters and Multi-Day Routes

Simpson Bay Lagoon to Grand Case

Board your yacht at Simpson Bay Marina or Isle de Sol by mid-morning. After a welcome champagne toast on the flybridge, exit the lagoon through the drawbridge and cruise north along the Dutch coast, rounding the island’s western tip past Baie Longue and Friar’s Bay. Anchor off Grand Case on the French north coast – roughly 10 nautical miles, an easy hour’s cruise. Spend the afternoon snorkelling Créole Rock and exploring the colourful village. In the evening, tender ashore for dinner on Grand Case’s restaurant row – Le Pressoir for classical French, Spiga for creative Italian, or one of the casual Creole lolos on the beach.

Tintamarre, Pinel Island and Orient Bay

Depart Grand Case early and cruise east to Tintamarre (roughly 6 nautical miles). Spend the morning snorkelling the nature reserve’s seagrass beds and rocky western shore – green turtles, rays and abundant fish life in crystal-clear water. Lunch on the aft deck with the uninhabited island as your backdrop. In the afternoon, cruise back to Pinel Island (3 nautical miles) for a relaxed swim and beach time on the marine reserve’s sand. Continue south to Orient Bay for an overnight anchorage – the reef-protected bay is calm and the beachfront bars offer a lively evening option if your group wants to go ashore.

Marigot, Maho Beach and Return to Simpson Bay

Cruise west to Marigot (roughly 8 nautical miles) for a morning ashore. Visit the open-air market (Wednesdays and Saturdays are the busiest and best), climb to Fort Louis for panoramic views over the harbour and across to Anguilla, and provision a few treats from the French bakeries and wine merchants. After lunch (on board or at one of Marigot’s waterfront restaurants), cruise south to Maho Beach for the afternoon jet-landing spectacle. Watch the heavies come in – KLM to Amsterdam, Air France to Paris, American to Miami – from the comfort of your aft deck with cold drinks in hand. Continue to Simpson Bay for a farewell dinner aboard or at one of the lagoon’s waterfront restaurants.

St Martin to Anguilla – Sandy Ground and Sandy Island

Depart Marigot or Simpson Bay mid-morning and set course north for Anguilla – roughly 10 nautical miles, under an hour at cruising speed. Clear customs at Road Bay (Sandy Ground) – the process is straightforward and typically takes under 30 minutes. Anchor in Road Bay and let your crew set up water toys in the calm, clear water. In the afternoon, cruise 15 minutes offshore to Sandy Island – a tiny cay surrounded by impossibly blue water, with a beach bar and some of the best swimming in the Leeward Islands. Return to Road Bay for dinner – tender ashore to Elvis’s Beach Bar for rum cocktails and local ribs, or try Veya for creative Caribbean fusion in a treehouse-style setting above Sandy Ground.

Prickly Pear Cays and Shoal Bay East

Cruise east from Road Bay to the Prickly Pear Cays – roughly 6 nautical miles, a 25-minute run. These twin cays offer crystal-clear water, vibrant living reef and outstanding snorkelling in shallow water that’s perfect for all abilities. The western cay is uninhabited and pristine; the eastern cay has two small beach restaurants. Lunch on the aft deck or ashore with your toes in the sand. In the afternoon, cruise to Shoal Bay East – Anguilla’s most celebrated beach, a long sweep of pinkish-white sand with turquoise shallows that extends for over a mile. Anchor offshore and swim in, or tender to Uncle Ernie’s Beach Bar for cold Heinekens and the view. Dinner at Blanchard’s on Meads Bay – one of the Caribbean’s finest restaurants, serving elevated Caribbean cuisine since 1994 – or the more casual Blanchard’s Beach Shack next door.

Little Bay, Maundays Bay and Rendezvous Bay

Cruise west along Anguilla’s south coast to Little Bay – a secluded cove accessible only by boat (or by rope descent from the cliffs above). The calm, glass-clear water is perfect for snorkelling and floating on inflatables. Your crew sets up a beach picnic on the small sand crescent. After lunch, continue to Maundays Bay – home to the Belmond Cap Juluca resort, its white Moorish arches curving along a half-moon of powder-white sand. Arrange a beachside lunch at Pimms (the resort’s oceanfront restaurant) or swim from the yacht. End the day at Rendezvous Bay – a 2-mile sweep of sand facing St Martin across the strait, with sunset views back towards the green mountains of the island you started from. Dinner at The Dune Preserve, Bankie Banx’s legendary beach bar on Rendezvous Bay, built from the hulls of old boats and driftwood – live reggae, rum punches and the stars coming out over the Caribbean.

Scilly Cay and Return to St Martin

Cruise east to Island Harbour on Anguilla’s north-east coast – a working fishing village with real Caribbean character. Wade across the shallows (or take a short tender ride) to Scilly Cay, a tiny private island with an open-air kitchen, cold rum punches and some of the best grilled lobster in the Caribbean. Spend the morning on the sand, then bid farewell to Anguilla and set course south for St Martin – roughly 10 nautical miles, arriving at Simpson Bay or Marigot by early afternoon. Time for a final provisioning stop, a sunset stroll through Philipsburg, or one last dinner at Grand Case before disembarking.

Guests looking for a longer voyage can combine the 3-day St Martin coast route with the 4-day Anguilla route for a comprehensive 7-day charter covering two islands, dozens of beaches and an extraordinary range of experiences – from French fine dining to British-Caribbean beach bars – without repeating a single stop. Add a few extra days and the 4-day St Barts route from the St Barts Itineraries section extends the voyage to a grand 8-day Leeward Islands circuit.