Experience an unparalleled journey with Sail La Vie(SLV), proudly certified by Sail Canada
Experience an unparalleled journey with Sail La Vie(SLV), proudly certified by Sail Canada
7-Day Sailing Adventure: St. Maarten – Anguilla – St. Maarten
Your Sailing Adventure Awaits!
Take off on a 7-day journey from St. Maarten to Anguilla and back, exploring some of the most stunning beaches, hidden cays, and peaceful bays in the Caribbean. With a perfect mix of adventure, relaxation, and exploration, this itinerary offers a unique way to experience the charm and beauty of both islands.
This itinerary highlights the natural beauty and serene vibe of Anguilla, paired with the vibrant culture of St. Maarten, creating a perfect balance for a Caribbean sailing adventure!
Flexible Itinerary: Please note that anchoring locations and activities may be adjusted based on weather conditions
and personal preferences, especially during inter-island passages.
Note: Itinerary options may vary depending on weather conditions.
- START HERE: Simpson Bay, St. Maarten (Dutch Side) Begin your journey in Simpson Bay, the lively heart of St. Maarten. This is the ideal place to enjoy water sports, stroll around the busy streets, and relax on the beach. In the evening, enjoy the famous nightlife, dine at waterfront restaurants, or visit Maho Beach to witness planes landing dramatically close to the beach. Prepare to set sail to Anguilla the next day.
- 1st Stop: Sail to Road Bay, Anguilla Set sail from St. Maarten to Anguilla, a short but exciting passage across turquoise waters. Anchor at Road Bay, Anguilla’s main port, known for its charming beachfront village and tranquil waters. Spend the afternoon exploring the local restaurants, relaxing on Sandy Ground Beach, or simply taking in the peaceful island vibe. Don’t miss the chance to enjoy a local seafood dinner at one of the island’s beachside restaurants.
- 2nd Stop: Shoal Bay, Anguilla Sail to Shoal Bay, often considered one of the most beautiful beaches in the Caribbean. This two-mile stretch of powdery white sand and crystal-clear waters is ideal for swimming, snorkeling, and sunbathing. The nearby coral reefs are home to vibrant marine life, making it a perfect spot for underwater exploration. Spend the day lounging on the beach or enjoying the calm, inviting waters.
- 3rd Stop: Meads Bay & Rendezvous Bay, Anguilla Continue to the breathtaking Meads Bay, where luxury meets serenity. Known for its calm waters and upscale beach resorts, it’s the perfect place to relax and enjoy Anguilla’s refined atmosphere. Afterward, sail to Rendezvous Bay, another pristine stretch of white sand, perfect for swimming and walking along the beach. The shallow waters here are ideal for a leisurely swim, and the views of St. Martin in the distance are spectacular.
- 4th Stop: Prickly Pear Cays Sail to the remote Prickly Pear Cays, two small uninhabited islands just off the coast of Anguilla. This hidden gem is a snorkeling paradise, with coral reefs teeming with tropical fish and vibrant underwater life. Spend the day snorkeling, swimming in the shallow waters, or relaxing on the deserted beaches. Enjoy a picnic lunch on board or on the beach, surrounded by stunning natural beauty.
- 5th Stop: Crocus Bay & Little Bay, Anguilla Anchor at Crocus Bay, a secluded beach surrounded by towering cliffs, perfect for a relaxing morning swim. Take a short hike up the cliffs for breathtaking views of the surrounding coastline. Then, sail to Little Bay, one of Anguilla’s most serene and secluded beaches, accessible only by boat. The calm waters are ideal for swimming and snorkeling, and the towering cliffs provide a stunning backdrop for a peaceful day on the water.
- FINISH HERE: Return to St. Maarten – Marigot Bay & Grand Case Sail back to St. Maarten and anchor at Marigot Bay on the French side. Explore the charming town of Marigot, with its French-Caribbean flair, local markets, and excellent restaurants. Then, make your way to Grand Case, known as the culinary capital of the Caribbean. Enjoy a gourmet dinner at a beachfront restaurant, stroll through the artistic Creole village, and reflect on your incredible journey before heading back to Simpson Bay.
Interested in learning more? Contact SLV at +1 647-261-9316
or feel free
And Here's The Best Part!
Discover How You Can Sail for Free from Your New Beautiful Florida Home
As a special gift to my clients, you can enjoy all these incredible experiences for FREE as part of our complimentary bonuses when you become a client of FloridianHome.ca. Conditions apply.
Don't miss this chance to create lasting memories on the waters of paradise—where luxury meets adventure!
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