Sail the Caribbean

The Caribbean is a significant topic for any vacation, especially sailing. Our suggestions focus on the areas easily accessible from St. Thomas, a popular Virgin Island charter base. Check out our recommendations for sailing the British Virgin Islands, the top Leeward Island sailing destination.

Let our crew handle all the details for you on one of our all-inclusive crewed catamaran charters; we offer these suggestions to help you plan a memorable Caribbean sailing vacation.

Our yachting destinations for yacht charters...

British Virgin Islands

  • Jost Van Dyke
  • Anegada
  • Virgin Gorda
  • Norman Island
  • Sandy Island
  • Salt Island
  • Cooper Island
  • Guana Island
  • Marina Cay
  • Peter Island

US Virgin Islands

  • St. John
  • St. Thomas
  • Water Island
  • St. Croix
  • Little Saint James Island
  • Buck Island
  • Hassel Island
  • Great Saint James Island

The Grenadines & Grenada

  • St. Vincent
  • Union Island
  • Tobago Cays
  • Palm Island
  • Carriacou Island
  • Mayreau Island
  • Baliceaux  Island
  • Petit St Vincent Island
  • Bequia
  • Mustique
  • Canouan

Other Islands & Hideaways

  • Saint Maarten/St Martin
  • Anguilla
  • St Barts
  • Antigua & Barbuda
  • Saint Kitts & Nevis
  • Salt Island
  • Montserrat
  • Guadeloupe
  • Dominica
  • Martinique
  • Trinidad
  • Saint Lucia
  • Barbados
pine island saint maarten, sint martin


This tranquil natural collection of sixty islands makes up a paradise for calm sailing in the British Virgin Islands.

crewed yacht chartering, aquanimity, sailing the virgin islands, st john


Explore St John and the Virgin Islands onboard our luxury yacht charter. We specialize in chartering the Caribbean and allowing our guests to explore at their leisure.

Experience the Caribbean when you sail aboard with our fun, experienced crew...

The Caribbean is a diverse and culturally rich region located in the western part of the Atlantic Ocean, southeast of the Gulf of Mexico. It comprises numerous islands, archipelagos, and mainland countries, and is known for its stunning natural beauty, warm tropical climate, and vibrant culture.

The Caribbean region comprises thousands of islands, large and small, along with some coastal areas of mainland countries. These islands are divided into several subregions, including the Greater Antilles (Cuba, Jamaica, Hispaniola, and Puerto Rico), the Lesser Antilles (a chain of smaller islands stretching from the Virgin Islands in the north to Trinidad and Tobago in the south), and the Bahamas.

The Caribbean enjoys a tropical climate characterized by warm temperatures year-round. It is known for its sunny weather, making it a popular destination for tourists seeking sun, sand, and sea. However, the region is susceptible to hurricanes during the Atlantic hurricane season, typically from June to November.

The Caribbean is a melting pot of cultures, with influences from Africa, Europe, Asia, and indigenous peoples. This cultural diversity is reflected in the region's music, dance, cuisine, and traditions. The primary languages spoken in the Caribbean are English, Spanish, French, and Dutch, depending on the specific island or country.

Caribbean cuisine is a fusion of flavors from various cultures. Common ingredients include rice, beans, tropical fruits, seafood, and spices like jerk seasoning. Popular dishes include rice, peas, roti, jerk chicken, and conch fritters.



Virgin Gorda Island

Experience the island of Virgin Gorda, home of the world-famous Baths. The Baths are as pristine as ever, including the famous pathway leading through the giant boulders to Devil’s Bay. Top of the Baths Restaurant is open with its delightful panoramic views and private pool; charter guests can swim at the Baths' private pool with a paid drink or dining.
The nearby marina at Virgin Gorda Yacht Harbor offers Wi-Fi, fuel, water, and ice, so the Captain and Chef may go and do some provisioning while you and your friends are exploring the area. The grocery store is a short walk, and some restaurants are open nearby that can be accessed by dinghy or taxi, including the all-new Snapper’s Bar & Grill and Coco Maya, which is a 10-minute walk from Spanish Town. Coco Maya (featured below) is a great spot to relax with a cocktail and meal. * A charter guest favorite!*
cocomaya virgin islands caribbean catamaran charters

Anegada Island

Take a taxi or scooter rental to Cow Wreck Beach Bar for lunch, where the locals are always friendly and the beaches are world-class. Don’t miss the nearby gift shops. Visit beautiful Loblolly Bay for excellent snorkeling, and stop at Big Bamboo for a cocktail or snack. Make reservations at Anegada Reef Hotel, Potter’s by the Sea (featured below), or Wonky Dog to tempt your taste buds with famous Anegada lobster for a delightful dinner ashore. Anegada Reef Hotel can also assist in organizing taxi transportation to make the most of your time on the island.

anegada island lobster haven