Leeward Islands Yacht Charter Overview
The Leeward Islands form one of the most iconic yacht charter regions in the Caribbean. Stretching from Anguilla in the north to Antigua in the south, this island chain offers short cruising distances, consistently good sailing conditions, and an exceptional diversity of landscapes and atmospheres.
From glamorous jet-set anchorages to quiet nature reserves and protected marine parks, the Leeward Islands are perfectly suited to luxury yacht charters designed around flexibility, comfort, and tailor-made itineraries.
Why Charter a Yacht in the Leeward Islands
The Leeward Islands are considered one of the most efficient and rewarding yacht charter regions in the Caribbean.
Ideal Cruising Distances & Conditions
Distances between islands are short, allowing guests to enjoy relaxed cruising days, frequent anchorage changes, and minimal passage times. The region benefits from reliable trade winds, calm anchorages, and year-round navigational comfort.
A Perfect Balance Between Luxury and Nature
The Leeward Islands combine high-end infrastructure—luxury marinas, refined dining, beach clubs and boutique shopping—with untouched bays, marine reserves, and protected coastlines accessible only by yacht.
A Region Built for Tailor-Made Yacht Itineraries
Whether guests are looking for a vibrant social scene, secluded anchorages, or a mix of both, the Leeward Islands allow itineraries to be adapted day by day, based on preferences, weather conditions, and pace.
Islands & Cruising Areas in the Leeward Islands
The Leeward Islands yacht charter region includes a wide variety of islands, each offering a distinct character and cruising experience.
Saint Barthélemy (St. Barth)
An international reference for luxury yacht charters. St. Barth combines spectacular anchorages, high-end restaurants, designer boutiques, and a vibrant social scene, particularly during the winter season.
Anguilla
Renowned for its pristine white-sand beaches, crystal-clear waters, and understated elegance. Anguilla offers relaxed cruising, excellent beach restaurants, and calm anchorages ideal for refined yacht charters.
Saint Martin / Sint Maarten
A unique dual-nation island offering lively marinas, provisioning facilities, international dining, and easy access to surrounding islands. A key logistical hub for many Caribbean yacht charters.
Antigua & Barbuda
One of the Caribbean’s great sailing destinations, with numerous bays, historic anchorages, and a strong maritime culture. Antigua also hosts world-class regattas and offers excellent marina infrastructure.
Saint Kitts & Nevis
A quieter, elegant cruising area featuring lush landscapes, protected bays, and Christophe Harbour Marina, one of the region’s premier luxury marinas.
Saba
A dramatic volcanic island known for some of the best diving in the Caribbean. Steep cliffs, marine reserves, and pristine underwater environments make Saba a standout stop for nature-focused charters.
Sint Eustatius (Statia)
A discreet destination rich in history and natural beauty, offering uncrowded anchorages, excellent diving, and preserved marine ecosystems.
British Virgin Islands (BVI)
Famous worldwide for easy cruising, sheltered waters, and iconic sites such as The Baths. The BVI are often combined with the northern Leeward Islands for extended itineraries.
United States Virgin Islands (USVI)
St. Thomas, St. John, and St. Croix offer a mix of protected national parks, vibrant ports, and relaxed cruising, often paired seamlessly with the British Virgin Islands.
A Luxury Yacht Charter Region Designed for Seamless Exploration
The Leeward Islands are particularly well-suited to crewed luxury yacht charters, allowing guests to explore multiple islands without ever repeating an anchorage. From glamorous ports to remote bays accessible only by sea, this region delivers one of the most complete yacht charter experiences in the Caribbean.
Whether combined with neighboring regions or explored on its own, the Leeward Islands remain a cornerstone destination for refined, flexible, and unforgettable luxury yacht charters.
