Leeward Islands

Experience the exotic cultures of both France and the Netherlands, including extreme dining, nightlife and relaxation.

St. Maarten is undoubtedly the world’s most popular winter cruising destination, and for good reason. Split equally between the culturally rich nations of France and the Netherlands, St. Maarten’s character is unlike any other in the Caribbean.

On the French side, enjoy decadent dining, boutique shopping or nude sunbathing on beautiful Orient Beach. On Wednesdays, Air France operates a jumbo jet that lands at Princess Juliana Airport, bringing with it France’s tastiest treats— including fresh mussels and a variety of yummy cheeses. Make sure to secure a spot at the Sunset Beach Bar before it lands, and watch in amazement as the giant plane lands precariously close to the ocean.

On the Dutch side, you’ll find discotheques filled with revelers dressed in high fashion, casinos for gambling and duty-free shopping. It’s also home to Simpson Bay Lagoon, the winter home of choice for yachts of all shapes and sizes. With access through “the bridge” spanning only 55 feet in width, during bridge openings the entertainment is marveling as captains expertly squeeze their multi-million dollar vessels through without garnering a scratch.

From St. Maarten, cruise south to what is hands-down the most luxurious Caribbean island, St. Barths. Many of the world’s wealthiest and most famous socialites frequent beautiful Saline Beach, as well as wine and dine at the ever-popular Nikki Beach Club. With high society glam sprinkled amongst the warm sunshine and gentle ocean breezes, it’s no wonder this island is the darling of the yachting community.

In Saba, a short cruise northwest from St Barths, enjoy a hike up Mount Scenery or scuba dive above a coral reef teeming with sea life. At dusk, marvel as your captain expertly anchors alongside Saba’s rugged cliffs for another beautiful evening on the sea.

And finally, another popular cruising destination is Anguilla, a flat, low-lying island of coral and limestone situated just a few miles north of St. Martin. Anguilla boasts several five-star resorts, including the Cuisinart, Maliouhana and Cap Jaluca all offering exceptional resort and fine-dining experiences. Go for an afternoon cruise around the island, taking in breathtaking views of white sandy beaches and soaring palm trees, or curl up on the aft deck with your personal copy of A Trip To The Beach, the charming true story behind one of the island’s most well known-restaurants, Blanchard’s. If you have time, tender ashore and stop in for a lobster dinner and their famous Cracked Coconut dessert. It’s a scrumptious treat of semi-sweet chocolate, homemade coconut ice cream and Kahlua custard sauce. Are you hungry yet? Anguilla offers something for everyone and should not be missed during your Caribbean charter vacation!

Sample itinerary

Day 1: St. Maarten

Begin your yacht charter vacation by boarding on the Dutch side of St. Maarten at the beautiful Simpson Bay Marina, located just minutes from the international airport and within walking distance to duty-free shopping and several restaurants. Relax onboard in the Caribbean sunshine, or venture along the waterfront enjoying the sights and sounds of the turquoise lagoon with its spectacular array of super yachts in various shapes and sizes.

Day 2: St. Barth’s

After breakfast, depart St. Maarten for a two-hour cruise south to the Caribbean’s most luxurious island, St Barth’s. Drop anchor in beautiful Anse de Colombier and take a refreshing dip in the ocean, marveling at the captivating resident sea turtles. In the afternoon head to the gorgeous sand dunes and crystal clear waters of Saline Beach.

Day 3: St. Barth’s

After breakfast, head to the main port and capital town of Gustavia for a day of shopping in its chic boutiques, duty-free shops and art galleries. Enjoy world famous restaurants offering everything from the best in French cuisine to open-air bars housed in buildings that date back to the early French settlers. Situated along the waterfront, make sure to stop by Le Select, the inspiration behind Jimmy Buffet’s “Cheeseburger In Paradise.” If you’re lucky, he may even stop in for an impromptu jam session.

Day 4: Saba

A short hop from St. Barth’s is the picturesque Dutch island of Saba. Enjoy an afternoon hike to the top of Mount Scenery, a potentially active volcano reaching almost 3,000 feet. The beautiful flora and fauna of the island will take your breath away. For lunch, stop in at one of the neighboring eateries offering the best in local seafood.

Day 5: Anguilla

Head to the beautiful low-lying island of Anguilla, known for its white sand beaches and beautiful palm trees. Curl up in a hammock and enjoy the balmy Caribbean breeze, or take a stroll along the sugar sand beaches and watch in awe as local fishermen bring in their daily catch.

Day 6: Anguilla

Head out for an afternoon trip to the beautiful Prickly Pear cays for a private lunch of grilled lobster and local caught fish. Swim in the turquoise water and snorkel with sea turtles, rays and tropical fish. These cays capture the true essence of the Caribbean.

Day 7: Grande Case, St. Maarten

On your final day of charter, spend the day at anchor in Grande Case, St. Maarten. Have the crew take you wakeboarding, or go paddleboard over the clear turquoise water. For dinner, head into town and enjoy the sights and sounds of this beautiful French-Caribbean city. With open-air restaurants, live music and beautiful art crafted by the locals, this gem of St. Maarten should not be missed.

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