St Martin Sailing Itinerary For a Weeklong Crewed Yacht Charter
A private, crewed yacht charter through Saint Martin, St. Barts, and Anguilla is the perfect St Martin sailing itinerary for travelers seeking secluded anchorages, world-class snorkeling, vibrant island culture, and effortless relaxation.
With a professional captain handling every passage and a private chef preparing gourmet meals onboard, this itinerary offers the best of the Caribbean—equal parts adventure and indulgence. Whether you’re comparing private yacht charter St Martin experiences or simply dreaming of a stress-free escape at sea, this weeklong route delivers unforgettable moments from start to finish.
From chic afternoons in Gustavia to peaceful swims off uninhabited islands, this St Martin sailing itinerary is designed for guests who want the ultimate blend of luxury, freedom, and island-hopping beauty.
Marigo St Martin, near Simpson Bay
Day 1: Welcome to Saint Martin – Embark on Your Yacht Charter in St Martin (Simpson Bay)
Your journey begins upon landing at Princess Juliana International Airport (SXM). A private transfer brings 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—your first taste of what makes a yacht charter St Martin so special.
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.
Highlights of Your Day One St Martin Sailing Itinerary:
Private transfer to IGY Simpson Bay Marina
Cocktail welcome and chef-prepared meal aboard
Relaxing first sail and sunset at anchor
Optional post-dinner drinks ashore
Enjoy the stunning views of Gustavia Harbor in St. Barts, a vibrant destination
Day 2: Sail to St. Barts – Chic Vibes in Gustavia and St. Jean Beach
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—one of the great pleasures of a luxury yacht charter St Martin itinerary.
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 crystal-clear waters. Spend the day soaking up the glamour and energy that makes St. Barts such a highlight on many St Martin sailing charters.
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.
Highlights of Day 2:
Sail to St. Barts, relaxing on deck or fishing en route
Explore Gustavia’s boutique shops and harbor cafés
Swim and sip cocktails near St. Jean Beach
Chef-prepared dinner aboard under the stars
Optional drinks at Shellona Beach Club
Colombier Beach St Barts
Day 3: Secluded Snorkeling and Beach Picnic at Colombier Beach
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—exactly the kind of hidden gem guests dream of when booking a private yacht charter St Martin.
Spend the day enjoying peaceful surroundings, swimming in 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 panoramic views of the island.
As evening sets in, return to your yacht for another incredible meal onboard, perfectly paired with a Caribbean sunset.
Highlights of Day 3:
Snorkeling and sea turtle spotting at Colombier Beach
Paddleboarding, beachcombing, and calm waters
Chef-prepared beach picnic
Sunset cocktails and dinner aboard
Tintamarre, St. Martin
Day 4: St Martin Sailing Itinerary Highlight – Tintamarre Snorkeling Adventure
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 and a true centerpiece of any St Martin sailing itinerary.
Spend the morning snorkeling with sea turtles, stand-up paddleboarding, or exploring pristine beaches. Enjoy a freshly prepared seafood lunch aboard, then sail to Orient Bay, one of St. Martin’s most famous stretches of sand.
Highlights of Day 4:
Pristine snorkeling and marine encounters at Tintamarre
Lunch onboard, prepared with fresh local seafood
Beachside cocktails and relaxation at Orient Bay
Enjoying an epic sunset on the swim platform
Relax on the yacht, take the tender ashore for beachside cocktails, or stay aboard for a quiet evening dining under the stars.
Highlights of Day 4:
Pristine snorkeling and marine encounters at Tintamarre
Lunch onboard, prepared with fresh local seafood
Beachside cocktails and relaxation at Orient Bay
Grand Case is known as the Gourmet Capital of the Caribbean
Day 5: Culinary Indulgence in Grand Case
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 onboard, enjoy a leisurely lunch while taking in the view of the picturesque village. The afternoon is yours—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.
Highlights of Your Day 5 St Martin Sailing Itinerary
Snorkeling at Creole Rock, a vibrant underwater paradise
Afternoon exploring Grand Case or enjoying water sports
Gourmet dinner aboard, with an optional meal ashore
A typical setting of the outer cays that make up Anguilla.
Day 6: Anguilla – White Sands and Tranquil Cays
After breakfast, set sail for Anguilla, an island famed for 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, paddleboarding, or simply lounging on deck with a cocktail in hand.
For lunch, your chef prepares a fresh seafood feast, best enjoyed alfresco 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 a touch of nightlife, a short tender ride can take you to Elvis’ Beach Bar for relaxed island vibes and live music.
Highlights of Day 6:
Sail to Anguilla, anchoring at Road Bay
Snorkeling and beachcombing at Sandy Island or Prickly Pear Cays
Paddleboarding, kayaking, or swimming in calm waters
Freshly prepared seafood lunch aboard
Sunset dining onboard, with an optional visit to Elvis’ Beach Bar
Phillipsburg, St Martin - a charming French town with a vibrant waterfront and boutique shops.
Day 7: Return to Saint Martin – The Perfect Finish to Your St Martin Sailing Charter
On your final full day, enjoy a relaxed morning swim and one last breakfast on deck before sailing 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—one of the most peaceful moments in this St Martin sailing itinerary.
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 near the marina.
As the sun begins to set, enjoy one final toast with your crew, followed by a gourmet farewell dinner onboard. Your captain will anchor in a peaceful bay, allowing for a final night of relaxation and stargazing.
Highlights of Day 7:
Scenic return sail to Saint Martin
Explore Marigot’s French-inspired shops and cafés
One last paddleboard or snorkel session near the marina
Final chef-prepared dinner aboard with sunset cocktails
Day 8: Farewell to Paradise
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 handles 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 week at sea—an experience that captures the very best of a St Martin yacht charter vacation.
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