The Leeward Islands are a beautiful chain of islands in the eastern Caribbean. They stretch from Puerto Rico to Martinique. And the gorgeous chain brushes up against the western Atlantic ocean. The stunning views of the mountainous islands are unmatched, and the white sand beaches are the perfect place to relax and unwind. We have plenty of yachts that will take you to any of these lovely places! Click here for a list of the boats we offer.

US Virgin Islands

The US Virgin Islands are some of the prettiest islands in the Caribbean. The USVI is made up of St. Croix, St. Thomas, and St. John. They are some of the more urbanized islands that offer great shopping, restaurants, and shore excursions. While city life on these islands is excellent, they also offer beautiful beaches. If you want to have a fantastic mix of shopping, eating out, and relaxing beachside, these islands are calling your name!

St John
Caring Crew with booking a yacht vacation

The British Virgin Islands

The British Virgin Islands are close neighbors to the USVI’s. The BVIs are comprised of TortolaVirgin GordaJost Van DykeCooper Islands, and many smaller islands. The British Virgin Islands are smaller and offer an incredibly relaxing experience. Tortola is the largest island and is home to the only airport in the BVIs. And Tortola provides a beautiful starting point for many of our charters. The BVIs are one of the most photographed places on earth! And they are home to one of the biggest New Year parties on the planet.


Anguilla is one of the northernmost Leeward Islands and is a close neighbor to St. Martin. Anguilla is a lesser-known island. But, the island is one of the hidden gems of the Caribbean. Anguilla is home to long stretching white sand beaches. And they are Famous for Rendezvous Bay, which overlooks St. Martin.

St. Martin

St. Martin is an incredibly unique island in the Leeward Islands. It is actually two different countries! So, one half is French-owned, and the Dutch own the other half. The beaches on St. Martin are gorgeous. The stunning island is home to an incredibly friendly and welcoming population. St. Martin is a must-see in the northern Leeward Islands, especially with Anguilla so close! Don’t forget to check out our blog entry on St. Martin here.

Caribbean Sailing Charter Boat

St. Kitts

The beautiful island of St. Kitts. St. Kitts is in the heart of the Leeward Islands. And it is home to a volcano! Mt. Liamuiga is a dormant volcano on the western side of the island. The Volcano brings in thousands of tourists annually and offers stunning island views. So, thrill-seekers welcome! Mt. Liamuigia provides a challenging hike but is well worth the workout.  And if volcanos aren’t your thing, St. Kitts also has dozens of stunning beaches.

Barbuda and Antigua

Barbuda and Antigua is the scuba diver and snorkeler’s dream. The island is famous for its reef-lined beaches. Coral reefs are home to thousands of fish and other aquatic animals. And if you prefer to stay dry, Barbuda is home to stunning pink sand beaches. The pink sand offers a fantastic contrast with the crystal clear blue waters of the Caribbean.

Barbuda Beaches


Guadeloupe is one of the best-kept secrets in the Caribbean. Jacques Cousteau himself feel in love with the scenery of this Leeward Island. The scenery both above and below the sea. Scuba diving on Guadeloupe in incredible. And the reefs are unlike anything else in the Caribbean. Click here for more information on this beautiful oasis.


Montserrat is one of the smallest islands in the Leeward Islands. The island is only 10 miles wide and holds a population just shy of 5,000. The island is the symbol of strength in the Caribbean. In 2010, a volcanic eruption destroyed much of the island’s key infrastructure. And now, the island is bringing in over 20k tourists a year! Due to the explosion, the island now has gorgeous black sand beaches that give it a unique feel.

What are you waiting for?

There are so many Leeward Islands worth visiting. Many of the islands are missing airports or impossible to access without a boat. So, why not charter a yacht and sail to these beautiful islands? Don’t miss the chance to see some of the world’s prettiest and well-kept secrets.