Leeward Islands Yacht Charters

The Leeward Islands yacht charters offer the perfect combination of luxury and adventure. This enchanting Caribbean archipelago boasts perfect white-sand beaches with crooked palms, celestial blue waters, and impeccable views.

Dotted with the remains of old military forts and sugar plantations, the Leeward Islands are bursting at the seams with an interesting history. Each of the Leeward Islands has unique features, making the islands a mosaic of diverse landscapes and cultures.

St Martin is known for its vibrant nightlife with nightclubs and casinos and duty-free shopping. St Barts is a hot spot with designer shops and high-end restaurants. On the other hand, Anguilla is quiet and serene with miles of sandy beaches. Saba is a diving paradise and St Kitts boasts one of the best golf courses in the Caribbean.

Leeward Islands Yacht Charter Highlights

  • Natural beauty
  • Varied cultural history
  • Exceptional diving and snorkeling
  • Luxury resorts and spas
  • Great party spots
Find Your Dream Yacht

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Most Popular Leeward Islands

St Maarten / St Martin

Two countries share the island of St Maarten /St Martin – France in the north and the Netherlands in the south. This island is known for its great restaurants, vibrant nightlife, and upscale resorts. Most yacht charters in the Leeward Islands start here.

St Barts

Also called the French Riviera of the Caribbean. This is the most exclusive of all the Leeward Islands and a destination frequented by celebrities and A-listers.


A quieter island in the Leeward Islands with beautiful sandy beaches and some of the best beach bars. If you are looking for a low-key island with amazing beaches and beautiful landscape, then Anguilla should be on your list.


Antigua is one of the two islands that make up the Caribbean nation of Antigua and Barbuda. The island is known for its historic sites and 365 sandy beaches.

St Kitts and Nevis

This dual-island nation is known for its old sugar plantations, wonderful beaches, and nature walks. St Kitts is the more developed of the two islands.

When to Go


Leeward Islands Yachting Season: mid-November through May

December through May is considered high season in the Leeward Islands, with Christmas and New Year being the most popular time for yacht charters. Most yachts charge a premium for Holiday charters because of high demand.

Many yachts relocate to other charter areas after May (from the Bahamas to New England to the Mediterranean) so the selection of charter yachts is limited in the summer months.

Why Charter a Yacht in The Leeward Islands?

Anguilla island sandy beach

Natural Beauty of the Leeward Islands

From the coastal beaches of Anguilla and St. Bart’s to the volcanoes of St. Kitts, the Leeward Islands feature lush tropical landscape and miles of sandy beaches. Lucky charter guests can explore this tropical paradise up close and personal.

Varied Cultural History

Though different in nature, the Leeward Islands all share a reverence for other cultures – especially considering their diverse origins. Take St. Maarten, for example, which houses two cultures in one; one half of the island is French, while the other is Dutch.

Exceptional Diving

With its vibrant corals and tropical fish, the Caribbean Sea is a prime spot for water sports enthusiasts; especially diving and snorkeling. With its translucent blue hues and mild temperatures, this revered body of water is the perfect place to spot the most surreal sea life – even those swimming miles and miles away.

Luxury Resorts and Spas

While some of the islands are simple in nature, others were seemingly designed to cater to the rich and famous.  While on your Leeward Islands yacht charter, head to St. Bart’s crystal coast for some of the world’s most desired haunts: like the Eden Roc, Nikki Beach and more.

Unspoiled Cruising

Floating seemingly off the radar in the Caribbean Sea, the Leeward Islands offer perfect breezes for smooth cruising among islands.

Leeward Islands Yacht Charters – Things to Do & See

  • Horseback ride along the cliffs of St Barts.
  • Jump in and swim with the dolphins at Dolphin Discovery on Anguilla.
  • Play with the pros at Anguilla’s new 18-hole, Greg Norman-designed Temenos golf course. It has ocean views at every tee.
  • Visit the historic Nelson’s Dockyard in Antigua.
  • Take a hike on the verdant island of Saba.
  • Indulge in an afternoon of blissful swimming at the secluded beach at Anse du Gouverneur overlooking St Kitts, Saba, and St Eustatius.