Lush volcanic peaks, breezy passages and the Tobago Cays — the Windwards are the Caribbean at its most dramatic and wild.
The Windward Islands string south from St Lucia toward Grenada, named for lying more directly in the path of the trade winds. This is the Caribbean at its most lush and dramatic: rainforested volcanic peaks plunging to the sea, the iconic Pitons of St Lucia, and the marine wonderland of the Tobago Cays. The sailing here is livelier and more open than the sheltered Virgin Islands — longer, breezier passages between bigger islands — which makes it the ground of choice for confident sailors who want spectacle, culture and a genuine sense of adventure under sail.
Several of our crewed catamarans range through the Windward chain, ready to show you the wilder, greener side of the Caribbean.
External resources: Saint Lucia
A crewed catamaran is the ideal way to take on the Windwards. The passages are longer and breezier than the Virgins, so an experienced crew makes all the difference — handling the trade-wind sailing while you take in the scenery from the deck. In return you get the Caribbean’s most spectacular cruising: volcanic peaks, reef-fringed cays and islands with real culture and soul.
Lush, dramatic and authentic, the Windwards reward those who want their sailing with a sense of adventure.
Windward Islands offers some of the most rewarding sailing in the Caribbean — dramatic islands within reach, trade-wind passages, and anchorages from lively to utterly secluded.
Anchor beneath the twin volcanic spires rising sheer from the sea — the most iconic landmark in the Caribbean.
Anchor inside a horseshoe reef in a marine park, snorkel with turtles, and feast on lobster grilled on a deserted beach.
The loveliest of the Grenadines — a sleepy, characterful island of boatbuilders, beach bars and easy charm.
A hurricane-hole anchorage of jaw-dropping beauty, ringed by rainforest and once called the prettiest bay in the Caribbean.
Explore nutmeg plantations and old rum distilleries on the fragrant Spice Island at the chain’s southern end.
A classic southbound run through the heart of the Windward chain — breezier sailing and spectacular anchorages, tailored by your crew.
Boarding in Le Marin, then a quick crossing south to St Lucia. Anchor between the iconic Pitons of Soufrière — a UNESCO site — for the most cinematic first night of any Caribbean trip.
A short morning sail to St Vincent. Anchor at Wallilabou — the Pirates of the Caribbean filming village — and explore the rainforest waterfalls inland.
A downwind hop to Bequia, the most charming of the Grenadines. Lunch at anchor, afternoon ashore in Port Elizabeth’s small harbour.
Sail to Mustique — strictly private, but accessible by yacht. Anchor in Britannia Bay and dine at Basil’s Bar, the storied beach club.
A morning passage to the Tobago Cays Marine Park — a horseshoe of uninhabited islets ringed by a reef. Snorkel with turtles, lunch on the boat, swim until sunset.
A short sail to Union for a beach day at Happy Island — a tiny conch-shell bar built on a sandbar. Evening anchorage in Chatham Bay’s calm wilderness.
A final passage south to Grenada (or back north to Mustique by request). Disembark in St George’s after a closing brunch on deck.
The Windwards offer the Caribbean’s most dramatic scenery — the Pitons, the Tobago Cays, lush volcanic islands — and a livelier, breezier sail. The British Virgin Islands are calmer and more sheltered, better for first-timers and families. The Windwards suit confident sailors after spectacle and adventure.
They can be, with a fully crewed yacht, but the longer open passages and stronger trade winds make the Windwards better suited to those with some sailing experience or a sense of adventure. Families and first-timers often prefer the sheltered BVI. Our team will advise based on your party.
December to April is prime season: reliable trade winds, warm sun and little rain. The trade winds are stronger here than in the Virgins, making for exhilarating sailing. The June-November hurricane season is avoided.
Most begin in St Lucia (Rodney Bay) or Martinique, both with international airport connections. Our team coordinates flights and transfers, and can arrange private aviation.
The Tobago Cays are a protected marine park: a cluster of uninhabited islands sheltered behind a horseshoe reef, with turquoise water, snorkelling among turtles, and lobster grilled on the beach. It’s one of the Caribbean’s great anchorages.
Breezier and more open than the Virgin Islands: longer passages between larger islands, with steady-to-strong trade winds. Thrilling sailing, best enjoyed with an experienced crew at the helm.
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