8 Days in St. Martin/St. Maarten, Anguilla, and St. Barts/ St. Barths

The Leeward Islands, St. Martin, Anguilla, and St. Barts, offer an elegant blend of French sophistication, Dutch charm, and barefoot Caribbean beauty. With steady trade winds and turquoise waters, this region is ideal for a relaxing yet adventure-filled charter. Explore gourmet dining in St. Martin, unwind on Anguilla’s endless white beaches, and soak up the chic allure of St. Barts. This round-trip 8-day itinerary will guide you on an unforgettable journey through some of the Caribbean’s most iconic and diverse destinations, from lively beach clubs and glamorous harbors to secluded coves and coral reefs teeming with marine life.

Day 1: St. Martin to Grand Case

Begin your charter with a short sail up the coast to Grand Case, known as the Gourmet Capital of the Caribbean. Anchor off the beach and take a tender ashore to enjoy boutique shopping or a sunset cocktail at a beachfront café. Dinner options range from fine French dining to relaxed “lolos” serving local barbecue. Grand Case is the perfect introduction to St. Martin’s French flair, culinary excellence, and warm island spirit.

Day 2: Grand Case to Tintamarre & Pinel Island

After breakfast, cruise a few miles to Tintamarre, an uninhabited island within a marine reserve. Snorkel among turtles and rays, then stroll along its untouched beach. Enjoy lunch aboard and then swim in the island’s calm turquoise waters before a short sail to Pinel Island, where rustic beach restaurants and shallow lagoons await. Spend the night at anchor nearby, with dinner served aboard under a blanket of stars.

Day 3: Pinel Island to Anguilla

Sail across the channel to Anguilla, a serene island known for its long white-sand beaches and tranquil anchorages. Drop anchor at Rendezvous Bay, one of the island’s most stunning stretches of shoreline. Go ashore for a swim, beach walk, or lunch at a chic seaside restaurant such as The Dune Preserve or CuisinArt Beach Club. Enjoy a relaxed evening aboard, watching the sunset paint the bay in hues of gold and pink.

Day 4: Anguilla

Cruise along Anguilla’s southern coast to Meads Bay, where calm waters and luxury resorts line the beach. Enjoy snorkeling, paddleboarding , and some relaxation. In the afternoon, head offshore to Sandy Island, a small coral cay surrounded by shimmering turquoise waters, ideal for swimming and sunbathing. Savor a beachside rum punch and grilled lobster before returning to your yacht for a peaceful night at anchor.

Day 5: Anguilla to St. Barts (Gustavia)

Set sail early for the scenic passage to St. Barts, a favorite destination for sailors and jet-setters alike. Enter Gustavia Harbor, lined with luxury yachts, designer boutiques, and elegant cafés. Explore the town’s charming streets, visit Fort Gustav, or enjoy an afternoon of shopping. Dine ashore at one of Gustavia’s renowned restaurants, such as Bonito or Bagatelle, before returning to your yacht for a restful night in the harbor.

Day 6: St. Barts (Colombier Bay & Shell Beach)

Cruise around to Colombier Bay, accessible only by boat or hiking trail. This secluded anchorage offers pristine snorkeling, calm waters for paddleboarding, and spectacular coastal views. Spend the afternoon swimming and relaxing on deck before returning to Gustavia. In the evening, enjoy sunset cocktails at Shell Beach followed by a starlit meal prepared by your chef.

Day 7: St. Barts to St. Martin (Simpson Bay)

Sail back toward St. Martin, anchoring in Simpson Bay, the yachting hub of the Dutch side. Enjoy lunch on board before going ashore to explore the marina village. Simpson Bay offers excellent restaurants, lively nightlife, casinos, and beach bars such as Karakter and The Greenhouse. Spend your final evening celebrating your week aboard with a farewell dinner and tropical cocktails overlooking the lagoon.

Day 8: Disembark St. Martin

Enjoy a relaxed breakfast on deck as you cruise to your final anchorage or marina. Take a morning swim or stroll along Simpson Bay Beach before saying farewell to your crew. If you’re flying home, Princess Juliana International Airport (SXM) is just minutes away. Depart with sun-kissed memories of fine dining, turquoise seas, and the perfect blend of French elegance and Caribbean adventure.