Trade winds, turquoise water and a thousand anchorages — the Caribbean is where catamaran sailing was born to be.
The Caribbean is the world’s most complete sailing playground: a great arc of islands curving from the Bahamas down to the coast of South America, each with its own rhythm, culture and colour. Steady trade winds make for reliable, rewarding sailing; short hops between islands mean more time at anchor than under way; and the water — every shade of blue imaginable — is warm year-round. From the sheltered, beginner-friendly Virgin Islands to the wilder, windier Windwards, a private crewed catamaran lets you take the islands at your own pace, dropping anchor wherever the day leads.
Several of our crewed catamarans are based in the Caribbean through the winter season, ready to show you the islands from the deck.
A crewed catamaran is the definitive way to experience the Caribbean. The trade winds make for dependable sailing, the distances are forgiving, and a catamaran’s shallow draft opens up anchorages a monohull can’t reach. Your crew handles the sailing, the cooking and the local knowledge — which beach bar tonight, which reef at dawn — while you simply enjoy the islands.
Whether you want the gentle, sheltered Virgins or the breezier Windward chain, our Caribbean fleet pairs you with the right yacht and crew for your party and your season.
The Caribbean offers some of the most rewarding sailing in the world — steady trade winds, hundreds of islands within easy reach, and anchorages that range from buzzing beach bars to utterly deserted cays.
Swim and scramble through a surreal landscape of giant granite boulders and hidden grottoes, one of the Caribbean’s natural wonders.
Anchor in a marine park inside a horseshoe reef, snorkel with turtles, and lunch on lobster grilled on the beach.
Sail beneath the twin volcanic spires rising sheer from the sea, the most dramatic landmark in the Caribbean.
From Foxy’s to the Soggy Dollar, the Caribbean’s legendary anchorage bars are a cruise highlight in their own right.
Steady 15-20 knot easterlies and warm water make Caribbean sailing as good as it gets, season after season.
Each cruising ground suits a different trip. A quick guide to choosing — your team will tailor the detail.
Welcome aboard in Marigot, then a short crossing to St Barths. Anchor at Anse de Colombier for a first swim, then Gustavia for an evening ashore.
A morning sail south to St Kitts and a tour of the UNESCO Brimstone Hill Fortress, with the evening at anchor in Whitehouse Bay.
A relaxed crossing to Antigua’s English Harbour. Walk Nelson’s Dockyard before dinner among the restored Georgian arsenals.
Sail south to Guadeloupe — Pigeon Island for a snorkel in the Cousteau Reserve, then Pointe-à-Pitre for the night.
A short morning sail to the Saintes archipelago — one of the most beautiful bays in the Caribbean by many lists. Lunch ashore, afternoon at anchor.
Cross to Dominica — the wildest of the islands. Hike to Trafalgar Falls or simply enjoy the silence of Prince Rupert Bay.
A relaxed final passage to Le Marin, with one last swim stop along the way.
December to April is the prime season: reliable trade winds, warm sunny days and little rain. This is the Caribbean high season. May and late November are quieter shoulder months. The official hurricane season runs June to November, when most charter activity pauses.
It depends on your party and experience. The British Virgin Islands are ideal for families and first-timers — sheltered and forgiving. The Windward Islands suit confident sailors wanting drama and breeze. The Leewards offer variety, and the Bahamas are unmatched for clear water and seclusion. Our team will match you to the right islands.
Very much so, especially the British Virgin Islands, where short hops and calm, sheltered waters make sailing easy and safe for children. Warm water, gentle anchorages and plenty to do ashore make the Caribbean one of the best family sailing destinations in the world.
Most charters focus on one cruising ground per trip, since the islands are spread across a wide arc. You typically fly into a gateway (Tortola for the BVI, St Lucia or Martinique for the Windwards) where your yacht and crew await. Our team coordinates flights and transfers.
Trade-wind sailing: steady easterly winds of 15-20 knots and warm water. The Virgin Islands offer the calmest, most sheltered conditions; the Windward and Leeward chains have more open passages between islands and a livelier sail.
No. All our Caribbean catamarans are fully crewed, so an experienced skipper and crew handle everything. You simply enjoy the islands. The Virgin Islands in particular are wonderfully relaxed for those new to yachting.
A great deal: snorkelling and diving on coral reefs, paddleboarding in turquoise bays, beach-bar hopping, island hikes to volcanic peaks, visiting historic harbours, and simply swimming off the back of the yacht. Your crew tailors each day to your party.
Every journey begins with a conversation. Tell us what you have in mind — dates, destinations, group size, experiences — and your Odyssea agent will craft a proposal tailored precisely to you.
An invitation-led membership for travellers who choose the ocean often. Preferred rates on yachts and villas, early access to themed departures, and bespoke journey design from our concierge — reach out to find out more.
“The magic of the Eastern Caribbean was not lost on us! Captain Florian and chef Mike were amazing! They planned the perfect agenda for us, carefully listened to our preferences for food and activities, and executed a dream vacation in a time when we really needed to get away from the stresses back home. Florian’s knowledge and experience were evident from day one, and Mike’s culinary expertise was truly on par with any restaurant in the world. Don’t pass up the opportunity to sail on Purpose!”
