Luxury Sailing yachts for charter Windward Islands

Sail the southern Caribbean, from St Lucia’s dramatic coastline to the islands of the Grenadines

The Windward Islands offer a wonderful mix of open-water sailing and intimate island discoveries. St Lucia’s Pitons rise steeply above the sea, while the Grenadines are dotted with small harbours, colourful fishing boats and inviting anchorages. Spend time in Bequia, where boatbuilding remains part of island life, or explore the reef-fringed lagoons of the Tobago Cays. Your choice of islands will depend on where your charter begins, the length of your trip and the sailing conditions.

A private luxury sailing yacht lets you enjoy the trade winds as you travel between islands, with plenty to look forward to once you drop anchor. Snorkel above the seagrass beds of the Tobago Cays, where sea turtles are often spotted, or enjoy a leisurely lunch prepared on board. Your crew can also help arrange visits to local markets and small waterfront communities, adding a personal connection to the islands beyond their beautiful beaches.