A Leeward Islands yacht charter is defined by island-hopping, short Caribbean passages, clear-water bays and a blend of culture and coastline that shifts from French sophistication to untouched volcanic wilderness within a single day’s sailing. From Nelson’s Dockyard in Antigua to the natural swimming pools of Chaudiere and the windmill-studded shores of Marie Galante, routes are shaped around your pace, whether that means vibrant harbours and dining ashore or quiet anchorages and unhurried swim days onboard.
Princess curates each luxury yacht charter in the Leeward Islands around your timing and preferences, carefully matching yacht, crew and itinerary to your group so the experience feels seamless from embarkation to return.
The Leeward Islands are one of the Caribbean’s most rewarding cruising regions, where steady trade winds, warm temperatures between 24 and 29°C and short passages between contrasting islands mean more time exploring, swimming and unwinding at anchor.
The contrast between the lively marinas of Antigua and the remote natural pools of Dominica allows itineraries to move naturally between culture and wilderness. In peak season, the most popular anchorages fill quickly, which is why local insight and thoughtful planning are essential.
Sample eight-day route from Christophe Harbour
Colourful quaysides
Turquoise bays
Island living
The main charter season runs from December to May, when the trade winds are at their most reliable and the weather is settled and sunny. Temperatures average between 24 and 29°C throughout, with warm, calm water ideal for sailing and watersports.
The quieter shoulder months of November and May offer excellent conditions with fewer boats at the popular anchorages. The hurricane season runs from June to November, which is why advance planning is essential for summer travel.
These luxury yachts are crafted for Leeward Islands cruising, with outdoor living, swim stops and relaxed itineraries shaped around short Caribbean passages and the sheltered anchorages between Antigua and Guadeloupe.
December to April is peak season with the most settled conditions. May and November offer good sailing with quieter anchorages and more availability across the popular stops.
Typically 4–6 islands, depending on pace and routing. The route from Antigua through Guadeloupe and Dominica covers considerable variety within a comfortable week.
Yes. Short passages, warm calm water and a mix of beaches, nature stops and cultural visits make it well-suited to groups travelling across different ages.
Yes. The Windward Islands lie to the south and are a natural continuation. The US Virgin Islands and British Virgin Islands are within reach for longer charters.
View All
