A Windward Islands yacht charter is defined by island-hopping, short Caribbean passages, clear-water bays and a blend of dramatic volcanic scenery and laid-back island culture that rewards those who take the time to explore it properly. From the green hills of Marigot Bay in St Lucia to the turtle sanctuary at Bequia, the exclusive shores of Mustique and the uninhabited islets of the Tobago Cays Marine Park, routes are shaped around your pace, whether that means vibrant harbour towns and dining ashore or quiet anchorages and unhurried swim days onboard.
Princess curates each luxury yacht charter in the Windward 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 Windward Islands are one of the Caribbean’s most rewarding cruising regions, where steady trade winds and short passages between volcanic islands mean more time swimming, exploring and unwinding at anchor.
The contrast between the lively harbours of St Lucia and the uninhabited islets of the Tobago Cays Marine Park allows itineraries to move naturally between energy and wilderness. The islands here are less crowded and more authentic than many Caribbean destinations, which is why those who know the region keep coming back.
Sample eight-day route through the Windward Islands
Lush Rainforests
Secluded Bays
Island Hopping
The main charter season runs from December to May, when the trade winds are steady, the skies are clear and temperatures sit between 27 and 29°C. The water is warm throughout and the anchorages at the Tobago Cays and Mustique are at their best during this window.
The quieter shoulder months of November and May offer excellent conditions with fewer boats at the popular stops. The hurricane season runs from June to November, which is why advance planning and local knowledge are essential for summer travel.
These luxury yachts are crafted for Windward Islands cruising, with outdoor living, swim stops and relaxed itineraries shaped around short Grenadine passages and the sheltered anchorages between St Lucia and Union Island.
December to April is peak season with the most settled trade winds. May and November offer quieter anchorages with excellent sailing conditions.
Typically 5–7 islands across the Grenadines, depending on pace and routing. The route from St Lucia to Union Island covers considerable variety within a comfortable week.
Yes. Short passages, calm water in the protected Grenadine anchorages and a high concentration of swim stops and turtle encounters make it very family-friendly.
Yes. The Leeward Islands lie to the north and are a natural continuation. Grenada and Carriacou lie to the south for those who want to extend further.
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