Caribbean

Leeward Islands

Create Your Dream Trip

Sail into paradise with the Leeward Islands—where steady 15-20 knot trade winds, 26°C (79°F) waters, and over 300 days of sunshine create the perfect sailing playground. Explore 15+ stunning islands, from Antigua’s 365 beaches to St. Barths’ chic harbors. Whether racing or cruising, adventure and luxury await in the Caribbean’s premier yachting destination!

Navigation:

Leeward Islands Yacht Charters

The Leeward Islands, a jewel of the Eastern Caribbean, are a sailor’s paradise. Stretching from the British Virgin Islands (BVI) and the U.S. Virgin Islands (USVI) in the north to Antigua and St. Kitts in the south, this region boasts crystal-clear waters, steady trade winds, and a wealth of tropical destinations to explore. Ideal for both seasoned sailors and first-time charterers, the Leeward Islands offer a mix of relaxed cruising and thrilling adventures.

The British Virgin Islands are often regarded as the sailing capital of the Caribbean. With more than 60 islands, the BVI features short passages, calm seas, and sheltered anchorages, making it perfect for leisurely island-hopping. Highlights include the iconic Baths at Virgin Gorda, the lively beach bars of Jost Van Dyke, and the pristine reefs of Anegada. The neighboring USVI, comprising St. Thomas, St. John, and St. Croix, offers a vibrant mix of American influence and Caribbean charm. St. John’s Virgin Islands National Park is a haven for nature lovers, while St. Thomas is renowned for its duty-free shopping and vibrant nightlife. The combination of easy navigation and well-equipped marinas makes the BVI and USVI a favorite destination for bareboat and crewed charters alike.

Further south, islands like Antigua, known for its 365 beaches, and St. Kitts & Nevis, with their lush volcanic landscapes, add diversity to your itinerary. Each destination offers something unique, whether it’s exploring historic forts, snorkeling in turquoise lagoons, or savoring the local cuisine. With a yacht charter in the Leeward Islands, you have the freedom to tailor your journey. From secluded beaches to bustling harbors, every stop reveals a new facet of this tropical paradise. Set sail and experience the magic of the BVI, USVI, and beyond

Get in touch

Sail the Leeward Islands

Available Yachts

Our Leeward Islands yacht charters offer tailored itineraries to match your preferences. With an expert crew on board, explore pristine beaches, crystal-clear waters, vibrant coral reefs, and the unique culture of the Leeward Islands for an unforgettable and memorable journey.

Lagoon Seventy7
Guest Cabins: 4
Sleep: 8
Crew: 4

SY Aeolus

Length: 23.28 m (76.38 ft)
Price starts from: $84,000
Brand & Model: Lagoon Seventy7
Sunreef Yachts 80 Sail
Guest Cabins: 5
Sleep: 12
Crew: 4

SY Mischievous

Length: 23.87 m (78.32 ft)
Price starts from: $93,000
Brand & Model: Sunreef Yachts 80 Sail
Sunreef Yachts 70 Sail
Guest Cabins: 4
Sleep: 8
Crew: 3

SY Ocean Vibes

Length: 22.76 m (74.68 ft)
Price starts from: $66,500
Brand & Model: Sunreef Yachts 70 Sail
Sunreef Yachts 80
Guest Cabins: 1
Sleep: 9
Crew: 4

SY Shades of Grey

Length: 23.99 m (78.71 ft)
Price starts from: €70.000
Brand & Model: Sunreef Yachts 80
Gun Boat 72V
Guest Cabins: 3
Sleep: 8
Crew: 3

SY Wonderful

Length: 22 m (72.18 ft)
Price starts from: $59,000
Brand & Model: Gun Boat 72V
Marsaudon ORC 57
Guest Cabins: 6
Sleep: 8
Crew: 2

SY Avel Vaez

Length: 17.56 m (57.61 ft)
Price starts from: €19,400
Brand & Model: Marsaudon ORC 57
Sunreef Yachts 80 Sail
Guest Cabins: 4
Sleep: 8
Crew: 4

SY Endless Horizon

Length: 23.87 m (78.32 ft)
Price starts from: $96,000
Brand & Model: Sunreef Yachts 80 Sail
Fountaine Pajot Aura 51
Guest Cabins: 4
Sleep: 8
Crew: 2

SY Beyond

Length: 15.91 m (52.2 ft)
Price starts from: $25,900
Brand & Model: Fountaine Pajot Aura 51
Fountaine Pajot Ipanema 58
Guest Cabins: 5
Sleep: 8
Crew: 2

SY Olivia Charles

Length: 17.81 m (58.43 ft)
Price starts from: $25,500
Brand & Model: Fountaine Pajot Ipanema 58

Leeward Islands Yacht Charter Attractions

The Leeward Islands offer a blend of unique cultures, from the French sophistication of St. Martin to the British colonial history of Antigua. Each island has its own character, charm, and traditions, making every stop a new cultural discovery.

Explore the Leeward Islands' rich history and breathtaking landscapes, from Antigua’s Nelson’s Dockyard to Saba’s Mount Scenery. Discover pristine beaches, vibrant marine life, and iconic coastal landmarks across the region.

Leeward Islands Sample Itinerary

Embark on an unforgettable sailing journey through the Leeward Islands, exploring pristine beaches, vibrant marine life, and charming island culture. This week-long itinerary from Antigua to St. Martin blends relaxation, adventure, and discovery. The following itinerary is just a sample; the captain may modify it depending on weather conditions or guest requests.

Start your adventure in Antigua, the “Land of 365 Beaches.”Board your yacht in English Harbour, a historic hub and UNESCO World Heritage Site. Explore Nelson’s Dockyard, a beautifully restored Georgian-era naval base. Sail to nearby Pigeon Beach or Carlisle Bay for a leisurely swim and snorkeling. Enjoy dinner ashore at a waterfront restaurant before anchoring in the serene harbor for the night.

Discover the Leeward Islands by Sea

Discover the Leeward Islands by Sea