Leeward Islands, Caribbean
Overview
Destination Overview: St. Barths & St. Martin
A yacht charter in St. Barths and St. Martin offers an unparalleled blend of Caribbean beauty, European sophistication, and vibrant island culture. This captivating corner of the Leeward Islands is a playground for the discerning traveler, where turquoise waters lap against pristine white-sand beaches, and lush green hillsides are dotted with luxurious villas and charming Creole villages. The unique dual-nation island of St. Martin, with its Dutch and French sides, provides a fascinating cultural contrast, while the nearby island of St. Barths exudes an air of exclusive glamour and refined elegance. The close proximity of these islands, along with the unspoiled natural beauty of Anguilla, makes this region the perfect destination for an unforgettable island-hopping adventure.
The Allure of a Dual-Nation Paradise
St. Martin, the smallest landmass in the world to be shared by two different nations, offers a captivating blend of cultures. The Dutch side, Sint Maarten, is a bustling hub of activity, with its vibrant capital, Philipsburg, offering duty-free shopping, lively casinos, and a vibrant nightlife scene. The French side, Saint-Martin, exudes a more relaxed and sophisticated atmosphere, with its charming capital, Marigot, boasting a chic marina, gourmet restaurants, and a colorful Creole market. This unique duality allows you to experience two distinct cultures in a single day, from the lively energy of the Dutch side to the refined elegance of the French.
Ideal For
Yacht Recommendation
A 45–70m motor yacht suits the St. Barths scene — think large sun decks, beach clubs, and a helipad for island transfers. The harbour at Gustavia accommodates yachts up to 60m.
Duration
7 Days
Total Distance
165 nautical miles
Best Season
December – May
Region
Leeward Islands, Caribbean
Ports of Call
7 destinations
Ideal For
Luxury Seekers, Couples, Foodies, Nightlife Lovers
Daily Sailing Distances
YOUR JOURNEY
165 nautical miles across 7 extraordinary destinations. This is a sample itinerary — your captain will tailor every detail to your preferences.

Day 1
Your journey begins as you touch down at Princess Juliana International Airport (SXM), where your private transfer will whisk you away to Simpson Bay, the pulsating heart of St. Martin's Dutch side. Step aboard your magnificent charter yacht, where the crew awaits with a warm welcome and chilled champagne. After a brief safety overview and a tour of your floating villa, a light, delicious lunch will be served on the aft deck, offering your first taste of Caribbean paradise.
With customs formalities seamlessly handled by your captain, your yacht will navigate through the iconic Simpson Bay Bridge and into the turquoise expanse of the Caribbean Sea. Drop anchor in a secluded cove, where you can take your first refreshing dip in the crystalline waters. The afternoon is yours to enjoy the yacht's water toys, from jet skis to paddleboards, or simply bask in the sun on the spacious sundeck.
As the sun begins its descent, casting a golden glow over the horizon, enjoy handcrafted cocktails and delectable canapés prepared by your private chef. For dinner, you have the choice of an exquisite meal aboard the yacht or venturing ashore to experience the vibrant nightlife and world-class restaurants of Simpson Bay. We recommend a reservation at La Samanna, a legendary resort with a restaurant offering refined French-Caribbean cuisine and breathtaking ocean views.
St. Barth is duty-free — luxury shopping here can save 20-30% compared to mainland prices.

Day 2
Awaken to the gentle lapping of waves and a sumptuous breakfast on deck. Today, we cruise to the French side of the island, a realm of chic boutiques, art galleries, and gourmet bistros. We'll anchor in the beautiful bay of Marigot, the charming capital of French St. Martin. Spend the morning exploring the vibrant Creole market, where you can find local crafts, spices, and the famous infused rums of the island.
After a delightful lunch at a waterfront café in Marigot, indulge in some retail therapy at the luxury boutiques of the Le West Indies Shopping Mall. For the more adventurous, a hike up to the historic Fort Louis offers panoramic views of the island and the neighboring islands of Anguilla and St. Barths. Later, we'll cruise to the nearby Grand Case, a picturesque fishing village renowned as the culinary capital of the Caribbean.
Grand Case comes alive at night with a dazzling array of restaurants, from casual beachside eateries to Michelin-starred establishments. We highly recommend Le Tropicana for its classic French cuisine with a tropical twist, or La Terrasse Rooftop Restaurant for its stunning views and creative cocktails. After dinner, enjoy a digestif at a local jazz club before returning to the tranquility of your yacht.

Day 3
Today we set sail for the enchanting island of Anguilla, a British overseas territory renowned for its pristine white-sand beaches and turquoise waters. Our first stop is Road Bay, the island's main port of entry. After clearing customs, take a tender ashore to explore the charming village of Sandy Ground, with its colorful beach bars and laid-back atmosphere.
After lunch on board, we'll cruise to the nearby Sandy Island, a tiny, idyllic cay that is the epitome of a deserted island paradise. Spend the afternoon snorkeling in the crystal-clear waters, which teem with colorful fish and vibrant coral reefs. Or, simply relax on the powdery white sand and soak up the Caribbean sun. For the more active, the nearby Prickly Pear Cays offer excellent diving and kayaking opportunities.
As the sun sets, we'll anchor in a secluded bay and enjoy a spectacular Caribbean barbecue on the beach, prepared by your crew. With the stars twinkling overhead and the sound of the waves as your soundtrack, this will be an evening to remember. For those seeking a more lively evening, the beach bars of Sandy Ground offer live music and dancing under the stars.
The planes landing over Maho-style St. Jean Beach are a St. Barth tradition — grab a table at La Plage and watch the show.

Day 4
Wake up in the tranquil beauty of Crocus Bay, one of Anguilla's most stunning beaches. Enjoy a leisurely breakfast on board before taking a tender ashore to explore the dramatic cliffs and hidden coves of this secluded bay. For the adventurous, a climb to the top of the cliffs offers breathtaking views of the entire island.
After a final swim in the turquoise waters of Anguilla, we'll set sail for the legendary island of St. Barths, the jewel of the Caribbean. The sail is a beautiful open-water passage, offering plenty of opportunities for sunbathing, relaxing with a good book, or even trying your hand at sailing the yacht under the guidance of the crew. We'll arrive in the iconic harbor of Gustavia in the late afternoon, just in time for a spectacular sunset.
Gustavia is the glamorous heart of St. Barths, a playground for the rich and famous. The harbor is lined with superyachts, designer boutiques, and world-class restaurants. For dinner, we recommend a reservation at Bonito, a chic restaurant offering stunning harbor views and a creative menu of French-Latin fusion cuisine. After dinner, experience the vibrant nightlife of Gustavia at one of its many exclusive clubs, such as the legendary Le Ti St Barth.
Île Fourchue is uninhabited and has no facilities — it feels like discovering a deserted island. The snorkeling is some of the best in the Caribbean.

Day 5
Spend the morning exploring the charming streets of Gustavia, with its distinctive red-roofed buildings and Swedish colonial architecture. Indulge in some duty-free shopping at the designer boutiques of the Carré d'Or, or visit the historical Wall House Museum to learn about the island's fascinating history. For a panoramic view of the harbor, take a short hike up to the ruins of Fort Gustave.
After lunch at a chic café in Gustavia, we'll cruise to the nearby Shell Beach, a unique and beautiful beach made entirely of tiny shells. Spend the afternoon swimming, snorkeling, or simply relaxing on this one-of-a-kind beach. For a truly memorable experience, enjoy a sunset cocktail at the famous Shellona beach club, which offers stunning views of the sunset over the Caribbean Sea.
For your final evening in St. Barths, we have a special treat in store. We'll anchor in a secluded bay and enjoy a gourmet dinner on board, prepared by your private chef. Or, if you prefer, we can arrange a reservation at L'Isola, one of the most exclusive and sought-after restaurants on the island, renowned for its authentic Italian cuisine.

Day 6
Today we explore the more secluded and natural side of St. Barths. We'll cruise to the stunning Anse de Colombier, a pristine, crescent-shaped bay that is only accessible by boat or a 20-minute hike. This is the perfect spot for a morning of swimming, snorkeling, and paddleboarding in complete tranquility. The bay is part of a protected marine reserve, so the underwater life is abundant and colorful.
After a delicious lunch on board, we'll set sail for the nearby Île Fourchue, a small, uninhabited island with a dramatic volcanic landscape. The island is a protected marine park and offers some of the best snorkeling and diving in the Caribbean. Explore the underwater world, where you can encounter sea turtles, rays, and a kaleidoscope of tropical fish. For the adventurous, a hike to the top of the island's peaks offers breathtaking 360-degree views of the surrounding islands.
We'll anchor in the sheltered bay of Île Fourchue for the night, a truly magical experience. Enjoy a gourmet dinner on the aft deck, surrounded by the raw, natural beauty of this volcanic island. With no light pollution, the stargazing here is simply spectacular. This is the perfect opportunity to disconnect from the world and reconnect with nature.
Le Select is where Jimmy Buffett wrote 'Cheeseburger in Paradise.' Order the famous cheeseburger — it's still on the menu.

Day 7
Enjoy a final leisurely breakfast in the idyllic setting of Île Fourchue. Take one last swim in the crystal-clear waters before we set sail for our return journey to St. Martin. The sail back is a wonderful opportunity to relax and reflect on the incredible experiences of the past week. Keep an eye out for dolphins, which are often spotted playing in the yacht's bow wave.
We'll arrive back in Simpson Bay in the early afternoon, giving you plenty of time for some last-minute souvenir shopping or a final stroll along the beach. Enjoy a farewell lunch on board, where you can savor the last of your chef's culinary creations.
As your unforgettable yacht charter journey comes to an end, your crew will arrange for your private transfer to Princess Juliana International Airport for your departure. You'll leave with a treasure trove of memories, already dreaming of your next luxury yacht charter adventure in the Caribbean.
Pick up a bottle of rhum arrangé (rum infused with local fruits and spices) as the perfect St. Barth souvenir.
COMPLETE ROUTE
165 nautical miles across 7 destinations. Click any marker to explore that day's details.
Real photos from the stunning locations on this itinerary.
PERFECT YACHTS FOR THIS ROUTE
These superyachts operate in the region and are ideal for this itinerary. Your charter specialist will match the perfect vessel to your requirements.
Crewed superyachts available for charter — prices are weekly starting rates












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YOUR VOYAGE AWAITS
This itinerary is a starting point. Your dedicated charter specialist will refine every anchorage, restaurant reservation, and shore excursion to create a voyage uniquely yours.
Selected Itinerary
St. Barths & Caribbean Chic
Leeward Islands, Caribbean · 7 Days