St. Martin Sailing Itinerary: A 7-Day Crewed Week with St. Barts

Your journey begins upon landing at Princess Juliana International Airport (SXM). A private transfer will bring you to IGY Simpson Bay Marina, where your captain and crew warmly welcome you aboard. Settle into your cabin, enjoy a refreshing champagne toast and chef-prepared welcome platter, and take in the first views of your floating home for the week.

Spend the afternoon unwinding as your yacht sets sail for a calm anchorage nearby. If you're up for an adventure, hop on a paddleboard or snorkel the warm waters of Simpson Bay.

As the sun dips below the horizon, enjoy a beautifully curated first dinner aboard, featuring fresh Caribbean seafood and tropical flavors. Those interested in exploring can take the tender ashore for an optional nightcap at Sint Maarten Yacht Club or the lively Soggy Dollar Bar.

Wake up to the scent of fresh coffee and breakfast prepared onboard, then set sail for St. Barts, the Caribbean's most exclusive island. The two-hour sail offers the perfect opportunity to relax on deck or try your hand at deep-sea fishing along the way.

Arriving in Gustavia, take time to explore the chic harbor, browse boutique shops, or enjoy a French pastry from a waterside café. In the afternoon, your yacht anchors off St. Jean Beach, where you can swim, paddleboard, or snorkel in the crystal-clear waters.

Dinner is served aboard under the stars, featuring a gourmet multi-course meal paired with fine wines. Those interested in a night out can take the tender ashore for an optional drink at Shellona Beach Club or the lively Le Ti St. Barth.

Start your morning with a leisurely breakfast on deck, then cruise to Colombier Beach, one of St. Barts' most secluded and breathtaking anchorages. Only accessible by boat or a scenic hiking trail, this pristine bay offers fantastic snorkeling and calm waters for paddleboarding.

Spend the day enjoying the peaceful surroundings, swimming in the turquoise waters, or lounging on the beach with a private picnic prepared by your chef. For those looking to stretch their legs, a short hike rewards you with breathtaking panoramic views of the island.

As the evening sets in, return to your yacht for another incredible meal on board, perfectly paired with a Caribbean sunset.

After breakfast, set sail for Tintamarre, a stunning uninhabited island and part of the St. Martin Marine Reserve. The shallow reefs here are teeming with marine life, making it one of the best snorkeling spots in the region.

Spend the morning snorkeling with sea turtles, stand-up paddleboarding, or exploring the pristine beaches. Enjoy a freshly prepared seafood lunch aboard, then sail to Orient Bay, one of St. Martin's most famous beaches, known for its crystal-clear waters and soft white sand.

Relax on the yacht, take the tender ashore for beachside cocktails, or stay aboard for a quiet evening dining under the stars.

Sail a short distance to Grand Case, the "Gourmet Capital of the Caribbean." Spend your morning snorkeling at Creole Rock, one of St. Martin's most famous underwater sites, where coral reefs and tropical fish create a stunning dive experience.

Back on board, enjoy a leisurely lunch while taking in the view of the picturesque village. The afternoon is yours to enjoy—kayak along the coastline, take the tender ashore for boutique shopping, or simply unwind on deck.

Dinner is another exquisite meal prepared by your onboard chef, though guests have the option to dine ashore at one of Grand Case's renowned French-Caribbean restaurants.

After breakfast, set sail for Anguilla, an island famed for its powdery white sand beaches, crystal-clear waters, and laid-back charm. Your captain will anchor at Road Bay, where you can take the tender to Sandy Island or Prickly Pear Cays, two stunning offshore islets perfect for snorkeling and beachcombing.

Spend the afternoon enjoying snorkeling straight from the yacht, stand-up paddleboarding, or simply lounging on deck with a cocktail in hand. For lunch, your chef will prepare a fresh seafood feast, best enjoyed alfresco on the aft deck as you soak in the Caribbean breeze.

As the sun begins to set, return to your private anchorage and enjoy a peaceful dinner aboard under the stars. For those who want to explore a bit of local nightlife, a short tender ride can take you to Elvis' Beach Bar, where the relaxed island vibes and live music make for a fun but easygoing evening ashore.

On your final full day, enjoy a relaxed morning swim and a final breakfast on deck before setting sail back toward Marina Fort Louis in Marigot, Saint Martin. The two-hour sail offers time to reflect on your incredible week while basking in the warm Caribbean sun.

Upon arrival, spend the afternoon at your leisure—explore the charming streets of Marigot, browse French boutiques, or sip coffee at a waterfront café. If you prefer to stay aboard, take advantage of the yacht's water toys for one last snorkel or paddleboarding session in the tranquil waters near the marina.

As the sun begins to set, enjoy one final toast with your crew, followed by a gourmet farewell dinner onboard, showcasing the best flavors of the Caribbean. Your captain will anchor in a peaceful bay, allowing for a final night of relaxation, stargazing, and reminiscing about an unforgettable voyage.

Your final morning aboard begins with a relaxed breakfast and coffee on deck, taking in the last views of the Caribbean waters.

By mid-morning, your crew will handle all final arrangements, ensuring a seamless transfer to Princess Juliana International Airport (SXM) or your next destination. As you step off the yacht, take with you unforgettable memories of a luxurious, adventure-filled week at sea.