St. Barths Luxury Crewed Motor Yacht Itinerary | 2026 & 2027
Discover the Caribbean Leeward Island Charm from St. Martin to Anguilla on the Ultimate 7-Day Luxury Crewed Motor Yacht Itinerary
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
Nestled into the northern Lesser Antilles and boasting an intricate blend of French, Dutch, British, and African cultures, the Leeward Islands invite you to embark on a luxury crewed motor yacht for a week of ultimate discovery. With short cruising distances and a series of unique islands, you will move easily between St. Martin, Anguilla, and St. Barths. Enjoy a massage in one harbor and boutique shopping in the next, with each stop offering its own Caribbean expression.
Beginning in St. Martin, your gateway to the Leewards, you will have easy access to its major international airport, and a quick cruise to Anguilla to begin your Caribbean journey. Over the course of a week, you will explore the tapestry of culture that makes up this unique region. From hiking mountainous terrains and discovering the islands' rich culture to diving in vibrant reefs and exploring the shores with water toys, your week will come together effortlessly, topped off with the impeccable service of an attentive crew. Additionally, chartering over Christmas and New Year places you within the Caribbean’s most sought-after season, when the islands become a seasonal home to a recognisable global crowd.
With over twenty years of experience curating bespoke charter itineraries, the Boatbookings team arranges every detail from the moment you place an enquiry to disembarkation. Our 7-day sample itinerary is completely customizable and will hopefully inspire you to begin planning your next trip to the Leeward Islands.
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Map of Your 7-Day St. Barths Crewed Motor Yacht Itinerary
Day 1: Grand Case
Step onto your luxury crewed motor yacht at the Fort Louis Marina in Marigot Bay on St. Martin, where your crew will greet you. After a morning spent indulging in the famous fresh-baked baguettes and pastries from Marigot's local bistros, you are invited to settle into the sun deck as your captain cruises toward Grand Case to begin your incredible week in the Leeward Islands.
Cruise to Grand Case: Known for its picturesque fishing village and quaint West Indian inspired buildings, Grand Case welcomes you with art galleries, charming boutiques, and gourmet restaurants. As you journey here, get to know your crew and chat with your group about your most anticipated activities of the week.
Water Toy Excursions: Once anchored in Grand Case, you can dive straight into the crystaline waters with a SeaBob or wander ashore to stroll along the beach. The year-round water temperature averages at 80°F (26 °C), perfect for exploring or simply viewing from the sand.
Welcome Dinner: As the sun begins to make its final descent, you can either head into town for dinner or dine on the aft deck of your private yacht. If you are celebrating an anniversary or honeymoon charter, we suggest heading ashore to La Shambhala, a romantic spot with an incredible menu and waterfront seating.
Day 2: Anguilla
Whether you like to sleep in or wake with the sun, day two will unfold at your own pace as you cruise to the dreamy coast of Anguilla. With a private, untouched Caribbean feel, this island offers ultra-clear waters, desert beaches, and quiet bays that invite you to unwind and revel in the quiet atmosphere.
Snorkel at Flat Cap Point: Along the rugged coast of Anguilla lies Flat Cap Point, where the island's dramatic rock formations take center stage. The unique structure means a variety of marine life can find a home in its craters. From schools of reef fish to the occasional ray, there are many opportunities to grab epic photos with your underwater camera.
Lunch at Savi Beach Club: For lunch, head to Savi Beach Club to try their grilled mahi mahi and mango salsa. Their menu is a melting pot of Caribbean flavors and locally sourced ingredients, making it a must-visit spot. After a bite to eat, stroll along their white-sand beach for an afternoon in the sand.
Guided Jet Ski Tours: For a thrilling afternoon, talk with your crew about a guided Jet Ski tour around Anguilla. With calm waters and an endless shore to explore, this will be an unforgettable part of your day. You can even plan it around the sunset and watch the last rays of the day from the seat of your Jet Ski.
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Day 3: Prickly Pear Cays
A short sail northwest of Anguilla brings you to the twin islets of Prickly Pear Cays. This scrub-covered land boasts powdery-white sands and sapphire seas for your dream beach day. They are completely uninhabited, making this a prized stop on your luxury charter to spot reef fish, corals, and the occasional sea turtle. From snorkeling to water skiing, the day is entirely yours.
Prickly Pear Cays: With shallow reefs peppering the area, drift snorkeling is a must. Grab a mask and snorkel and simply float in the water, catching glimpses of vibrant corals and fish along the way. You can also explore above the surface with a paddleboard or kayak.
Beach Picnic at Prickly Pear Cays: Around lunch, pick your favorite stretch of white sand for a beach picnic. Your crew will prepare a standout array of your favorite dishes and chilled drinks for a laidback afternoon, followed by some beach games. If you seek a bit of a thrill, your captain can prepare the tender for an afternoon of wakeboarding or water skiing.
Seal Island Reefs: As part of a designated marine park, Seal Island Reefs offer a look into the thriving corals and diverse marine life of the Caribbean. Take snorkeling to the next level as you dive to get a closer look at eagle rays and nurse sharks. Optionally, you can schedule a guided dive giving the proper weather conditions.
Day 4: Île de la Fourche
Welcome to the fourth day of your luxury yacht charter vacation, where time becomes irrelevant. Today you will cruise toward St. Barths, stopping along the way for some snorkeling and a leisurely lunch ashore. While you journey south, enjoy an attentive espresso service on the sun deck as the morning sun warms your skin.
Tintamarre: The wild, undeveloped beauty of Tintamarre welcomes you for a spot of swimming and snorkeling in its surrounding aquamarine waters. Along the shore lies a cinematic beach where the only footprints in the sand are yours. As you stroll hand in hand with your loved ones, spot the occasional driftwood sculpture, carved with love by the sea.
Pinel Island: Upon anchoring in the protected mooring field, step ashore to the beach. Dotted with a handful of waterfront restaurants, this is a great opportunity to enjoy a relaxed lunch as you look out to the crystal-clear waters. After a quick bite, grab a paddleboard or E-Foil for an afternoon of effortless exploration.
Île de la Fourche: Settled between St. Martin and St. Barths, Île de la Fourche is completely uninhabited, with a rugged coastline and striking waters. The water clarity provides exceptional snorkeling and diving. Around sunset, take a short but steep climb to the peak of the island for sweeping views over St. Barths.
St. Martin Crewed Motor Yachts
Day 5: St. Barths
Wake slowly and step out of your cabins to a full breakfast on the aft deck. As you sip your coffee, your captain will pull into Gustavia Harbor on St. Barths, a picturesque anchorage framed by red-roofed buildings and a parade of superyachts. St. Barths hums with luxury, where designer brands lie on every corner street and celebrities choose to vacation.
Dive the Wreck of Nonstop: For an early morning dive, anchor near the Nonstop wreck, where a 200-foot luxury motor yacht sank in 1989, becoming an artificial reef for corals and fish. The site sits about 50 meters below the surface making it an intermediate dive.
Explore the Island: After a morning dive, step ashore to browse the array of exclusive boutiques and beaches. You can also rent a car and take a tour of the island, hopping between beach bars and cafes all afternoon. As you drive by, look out for the fabulous homes carved out of the hillsides.
Experience St. Barths' Nightlife: The nightlife of St. Barths offers lively Caribbean music, strong drinks, and a full dance floor. Enjoy jazz, cognac, wine, and laughter as you dance the night away with your group. When you are ready, head back to the boat for a restful night sleep.
Day 6: Colombier
Sail around the harbour to Anse de Colombier, where you’ll find a splendid beach that is only accessible by sea. As one of the most protected anchorages on St. Barths, Colombier is an excellent anchorage for a peaceful retreat. With desert beaches and unique fine-dining expereinces, the day will be simple, yet flawless.
Colombier Nature Reserve: As you anchor in Colombier, head ashore to the crescent beach, where powder-white sands welcome you for a relaxed beach day. With beach games or your favorite novel, it promises to be the perfect start to your day.
Water Toy Excursions: With a landscape of rolling green hills and crystaline waters, Colombier offer the perfect conditions for an afternoon filled with water toys. Your captain can prepare the tender for a tour around the island as you relax in a towable toy behind the wake.
Dinner at Le Tamarin: For dinner, you can head ashore to Le Tamarin, where an immersive rainforest setting will take you to a whole new world. The outdoor setting invites you to rest beneath the shade of century-old Tamarin trees and observe the small turtles in the ylang-ylang pond as you dine on their French-Caribbean menu.
St. Martin Crewed Motor Yachts
Day 7: Philipsburg and Simpson Bay
You will begin the journey back to St. Martin today, and as you cruise north, enjoy a lovely breakfast on the aft deck. With nowhere to be and nothing to do, you can relax on your final full day, creating the exact itinerary you want. From water toys in calm bay to shopping in local boutiques, the day is yours.
Cruise to St. Martin: While you cruise to St. Martin, take the time to stretch out on the sundeck with your coffee and some board games. Take advantage of the journey to get some sun before a day of further exploring St. Martin.
Shopping in Philipsburg: The colorful town of Philipsburg was built for a seamless blend of cruising convenience and onshore exploration. With duty-free shopping, you can grab everything from jewelry and watches to local crafts and souvenirs. For lunch, stop at one of the waterfront dining locations for a drink and small plates.
Simpson Bay: If you enjoy a casino scene, there is no better place to indulge than Simpson Bay. With a collection of casinos and piano bars, you can spend the afternoon testing your skills at a poker table or simply enjoying some music and your favorite cocktail.
Day 8: St. Martin
After a hearty breakfast of all your favorite breads and pastries, jump into the water for one last dip before gathering your tokens and bags. You will disembark at noon for onward travel. After a week of pampering, you will leave already excited to book your next trip. If you connected with your crew, be sure to exchange contact information so you can come back and charter with the crew you know and love.
St. Martin Crewed Motor Yachts
Leeward Islands Charter Guide | St. Martin | St. Barths | Anguilla | Antigua and Barbuda | Windward Islands
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