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Boats for Caribbean cruising

Practical Boat Owner

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February 2026

Phil Clandillon looks at the best second-hand yachts for crossing the Atlantic and sailing the Caribbean

- Phil Clandillon

Boats for Caribbean cruising

The Caribbean island chain stretches from Trinidad & Tobago in the southeast, all the way to The Bahamas in the northwest. Along the way, it takes in 13 independent countries and the same number of overseas territories. Outside the hurricane season, the trade winds blow steadily, the turquoise seas are warm, and there's a huge variety of beautiful cruising destinations to explore. In the north of the chain, the British and US Virgin Islands sit on their own shallow shelf, extending underwater from Puerto Rico. The islands and reefs on this bank offer protection from the swell, meaning yachts can cruise in shelter among the 90 or so islets and cays. Visiting the larger islands in the south means sailing in the true ocean. Most passages are possible in daylight, and others with one night at sea.

Pick up a buoy at Shoal Bay, Anguilla, and swim ashore to one of the world's best beaches. Anchor in Pitons Bay, St Lucia, beneath the famous twin volcanic peaks. Spend a night at Anse La Roche on Carriacou, and dine on fresh lobster and cocktails at Tim's Sunset Beach Bar. The Caribbean offers the perfect balance of open-water passages, idyllic anchorages and vibrant culture. But what boat should you choose to explore it in?

imageQualities to look for

Crossing the Atlantic from the UK is normally downwind, and many mainstream production boats make the journey every year.

A modern design with efficient ventilation, a spacious interior and a swim platform makes a lot of sense once you arrive. If you mean to sail back to the UK, however, it can be a tougher crossing, and you may prefer a more traditionally bluewater design. I've included models of each type, usually available in the UK or on the local used market.

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