The Best Sailing in the Caribbean

Waypoints Annapolis® can put the pristine islands of the US and British Virgin Islands within reach. From our Virgin Islands affiliate base on the East End of St. Thomas at Compass Point Marina, you can take in the culture and natural beauty of these unique Caribbean destinations with an unforgettable charter experience. The British Virgin Islands are hailed as the best sailing destination in the Caribbean, and arguably the whole world. The consistent trade winds, year-round warm weather, and line of sight sailing make the Virgin Islands ideal for your cruising adventure. With dozens of unspoiled islands and cays, beautiful white sand beaches, bountiful marine life, and a unique, relaxed island culture, the Virgin Islands are perfect for your next cruising adventure.

Sample Itinerary
Top Virgin Islands Destinations

St. Thomas & St. John

From the beautiful harbor of St. Thomas to the tranquility of St. John, there are endless opportunities to explore.

Charlotte Amalie’s historic shopping district is home to a range of superb restaurants, shops, and nightlife.

The island of St. John, the smallest of the three US Virgin Islands, is home to Virgin Islands National Park, 22 nature trails, wildlife, and extraordinary beaches.

St. Martin & Anguilla

St. Martin offers gourmet food, world-class duty free shopping, nightlife, pristine beaches, and a cosmopolitan lifestyle. Ample opportunities for high-class entertainment or low key relaxation await.

St. Vincent & The Grenadines

Set sail and hop between the remote coves and luxurious hideaways of over 30 islands, each offering white sand beaches and crystal blue waters.

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