7-Day St. Barths Luxury Crewed Catamaran Itinerary | 2026 & 2027
Charter a Luxury Crewed Catamaran and Explore the Unique Islands of St. Martin, St. Barths, and Anguilla
Day 1: Grand Case | Day 2: Anguilla | Day 3: Prickly Pear Cays | Day 4: Île de la Fourche | Day 5: St. Barths | Day 6: Colombier | Day 7: Philipsburg and Simpson Bay | Day 8: St. Martin
With the perfect blend of French, Dutch, British, and African cultures, the Leeward Islands welcome you for a week of adventure aboard a luxury crewed catamaran. Short cruising distances between St. Martin, Anguilla, and St. Barths encourage you to explore all the best the region has to offer. Anchor in Gustavia Harbor one morning for boutique shopping, then cruise over to Simpson Bay for a lively evening in town. However you like to spend your afternoons, each anchorage offers its own unique experiences.
Throughout your 7-day itinerary, witness the extraordinary blend of culture, geography, and cuisine. From hiking up to panoramic views to diving vibrant reefs, you can explore the rugged coastline however you like. With the care and attention of a professional crew, your birthday charter celebration or Christmas and New Year family reunion will leave you with nothing to do but enjoy time with loved ones. With a bespoke menu, your evenings will unfold effortlessly on the aft deck of your luxury catamaran as your private chef places each indulgent course in front of you.
The Boatbookings team is thrilled to help plan every detail of your luxury yacht charter. With over twenty years of experience in the yachting industry, we continue to create personalized itineraries filled with your must-see stops, hottest new water toys, and top activities. Our charter experts annually inspect each yacht, meet their crews, and sample their menus, ensuring we can match you with the best yacht possible. Whenever you are ready to begin planning your next trip, contact us for a proposal.
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Map of Your 7-Day St. Barths Crewed Catamaran Itinerary
Day 1: Grand Case
Your journey starts in the Fort Louis Marina in Marigot Bay on St. Martin at noon, where you will step onto your luxury catamaran and meet your crew. From the moment you step on board, they will handle every detail, allowing you to climb to the flybridge for panoramic views as you cruise toward Grand Case and begin your blissful week in the Leeward Islands.
Cruise to Grand Case: Begin with a short trip to Grand Case, where a small fishing village invites you to explore its array of local artisan shops and waterfront restaurants. As your captain steers the ship, sink into the trampolines and watch as the crystaline waters unfold before you.
Water Toy Excursions: Upon arrival, dive straight off the swim platform and into the water with a SeaBob or wander ashore to feel the sand between your toes. With 80°F (26 °C) water temperatures year-round, the water is perfect for a float or to admire from the beach.
Welcome Dinner: Your first night is a celebration of the week ahead. You can either head into town for dinner, or dine on the aft deck of your yacht as your professionally trained chef brings out your multi-course meal. For a romantic evening, La Shambhala is a fantastic option. Waterfront seating and fresh seafood make for the perfect spot to celebrate an anniversary or honeymoon charter.
Day 2: Anguilla
Enjoy a slow morning where you can wake early and watch the sunrise from the bow or sleep in before stepping out of your cabins for a gourmet breakfast and espresso. Today you will cruise to Anguilla, an island known for its secluded, unspoiled Caribbean charm. With crystal-clear waters, expansive sandy beaches, and quiet coves, you can fully relax and soak in the peaceful surroundings.
Snorkel at Flat Cap Point: Flat Cap Point is defined by striking rock formations that create a dramatic backdrop for your first snorkel session in the Leewards. Here you can find reef fish, and if you are lucky, the occasional ray. While you explore, your crew will stand by to capture incredible photos.
Lunch and Savi Beach Club: Around lunch time, make your way to Savi Beach Club for their grilled mahi mahi and mango salsa. With fresh, local ingredients and a Caribbean-inspired menu, you will leave feeling more than satisfied and energized for your continued adventures.
Tender Around Anguilla: Later in the afternoon, grab a mask and snorkel and hop in the tender for a guided tour along the coast of Anguilla. Your captain's local knowledge of the region will bring you to secluded coves only accessible by tender, meaning fewer crowds and more room to explore.
Day 3: Prickly Pear Cays
Day three of your luxury yacht charter brings you to the pristine shores of Prickly Pear Cays. With powdery-white sands and brilliant turquoise waters, the day is yours to spend exploring however you like. Drift snorkel over vibrant reefs and look out for reef fish, corals, and sea turtles. You can also speed across the water on your favorite water toy.
Prickly Pear Cays: While you cruise to Prickly Pear Cays, grab your favorite bathing suit so you can jump straight into the water for a drift snorkel when you arrive. The shallow waters make the perfect conditions for a peaceful float while you search for corals, fish, and shellfish. Alternatively, watch from above the surface on a paddleboard or kayak.
Beach Picnic at Prickly Pear Cays: For an afternoon at the beach, your crew can prepare a BBQ picnic with your favorite dishes. Settle into a shaded spot on the sand while the smell of the grill fills the air. The rest of the afternoon is yours to read your favorite novel, play some beach games, or simply soak up the sun.
Seal Island Reefs: As part of a protected marine park, Seal Island Reefs provide a glimpse into the Caribbean’s abundant marine life. Elevate your snorkeling experience by diving a little deeper for a closer encounter with eagle rays and nurse sharks. If conditions allow, you also have the option to arrange a guided dive.
Day 4: Île de la Fourche
Begin day four as you step out of your cabins to the stunning views of Prickly Pear Cays. Head to the flybridge for breakfast this morning while your captain cruises toward St. Barths. Along the way, you will stop for a bit of snorkeling and lunch ashore. The journey south gives you the opportunity to lounge on the sundeck of your Sunreef catamaran and take in the waters unfolding before you.
Tintamarre: Untouched and untamed, Tintamarre invites you to slip into its luminous turquoise waters for a refreshing E-Foil or Subwing session. Its shoreline feels almost otherworldly as you step onto its unspoiled stretch of sand, where you will be the only ones there. Wander along the coast with your loved ones and discover pieces of driftwood sculpted by the tides.
Pinel Island: Pinel Island welcomes you to its sandy shores, peppered with waterfront restaurants and boutiques. Your captain and crew will lead you to their favorite local spot for lunch, where you can enjoy your meal by the water with a perfect view of your yacht.
Île de la Fourche: Île de la Fourche lies between St. Martin and St. Barths, and is a dreamy spot for snorkeling and scuba diving. Completely uninhabited, the rugged coastline and impossibly clear waters provide extraordinary conditions. As the sun sets, take the path that leads to the island's lookout point for gorgeous views of St. Barths and the golden sky.
Day 5: St. Barths
Ease into the morning and emerge from your cabins to a freshly prepared breakfast on the aftdeck. With coffee in hand, watch as your captain glides into Gustavia Harbor in St. Barths. This postcard town offers a stunning landscape of red-roofed buildings and an impressive display of superyachts. The island excudes refinement, where high-end boutiques and cafes fill the streets.
Dive the Wreck of Nonstop: Begin your day with a dive at the wreck of Nonstop, a 200-foot luxury motor yacht that sank in 1989 and has since evolved into an artificial reef. About 50 meters below the surface, the side attracts vibrant marine life and is best suited for intermediate divers. Alternatively, you can ask your captain to prepare the tender for a wakeboarding or kiteboarding lesson.
Explore the Island: After your dive, head ashore to explore a mix of upscale shops and beautiful beaches. Consider renting a car to discover more of the island at your own pace, stopping at beach bars and cafes along the way. As you wind through the roads, take in the stunning villas built seamlessly into the hillsides.
Experience St. Barths' Nightlife: As evening falls, the island comes alive with Caribbean energy. Grab a cocktail and hit the dance floor of one of St. Barths' nightclubs while live music plays in the background. It promises to be a night of fine spirits and great company.
Day 6: Colombier
Take a morning cruise around the harbor to Anse de Colombier, a beautiful beach reachable only by boat. One of the most sheltered anchorages on St. Barths, Colombier offers a serene escape at sea. With secluded stretches of sand and a distinctive fine dining scene, the day will unfold effortlessly.
Colombier Nature Reserve: Once anchored in Colombier, step ashore to a sweeping crescent beach with soft white sand ideal for a slow, relaxed day. Whether enjoying beach games or paddleboarding, it sets an easy, unhurried tone for the day ahead.
Water Toy Excursions: Framed by green hills and clear, sparkling waters, Colombier provides ideal conditions for an afternoon on the water. Your captain can ready the tender for an island cruise while you experience the thrill of being pulled around on a towable toy for the afternoon.
Dinner at Le Tamarin: In the evening, head ashore to Le Tamarin, where a lush, rainforest-inspired setting creates a completely different atmosphere. Dine outdoors beneath the towering tamarind trees and watch small turtles glide through the ylang-ylang pond while enjoying a refined French-Caribbean menu.
Day 7: Philipsburg and Simpson Bay
Today marks the return journey toward Saint Martin, and as you head north, enjoy a leisurely breakfast served on the aft deck. With no set plans and no schedule to follow, your final day is entirely yours to shape. From playing with water toys in sheltered bays to browsing local boutiques, the choice is yours.
Cruise to St. Martin: As you sail toward St. Martin, relax on the sundeck with a coffee and a selection of board games. It's the perfect opportunity to soak up the sun and unwind before arriving for further island exploration.
Shopping in Philipsburg: The vibrant capital of Philipsburg is perfectly positioned for easy access from the harbour, making onshore exploration effortless. Duty-free shopping ranges from fine jewelry and watches to handcrafted souvenirs and locally produced art. For lunch, settle into a seat at one of the waterfront restaurants for a bite to eat.
Simpson Bay: For a livelier afternoon, head to Simpson Bay, known for its casinos and piano bars. Try your luck at the tables or simply relax with live music and a signature cocktail in hand as the afternoon drifts by.
Day 8: St. Martin
Your final morning on board will begin with a full breakfast on the aft deck, before you have the opportunity to jump off the swim platform for a dip in the warm Caribbean waters. At noon, your crew will assist you in gathering your things for disembarkation. You will step off the yacht feeling completely relaxed, if not a bit sad that the journey is over. However, if you particularly connected with your crew, exchange contact information so you can begin planning your next trip back and charter with the crew you know and love.
Leeward Islands Charter Guide | St. Martin | St. Barths | Anguilla | Antigua and Barbuda | Windward Islands
Caribbean Charter Guide | British Virgin Islands | US Virgin Islands | Caribbean
