The Best Caribbean Islands to Visit by Boat

The Caribbean by boat: choosing the right islands

The Caribbean trade winds blow from the north-east at a steady 15–25 knots from November through to May, creating the most reliable sailing conditions on earth. Warm water, short island-hopping passages, consistently beautiful anchorages and a rum-soaked beach culture that has captivated sailors for three hundred years. The only question is which part of the Caribbean to sail.

Each island group has its own character, its own sailing challenges and its own distinct culture. Here's the honest breakdown.

British Virgin Islands

The case for: The BVI remains the world's benchmark charter destination for good reason. The Sir Francis Drake Channel is sheltered, shallow and glittering. Passages between islands take one to three hours. Mooring balls eliminate anchoring stress. The Soggy Dollar Bar, The Baths at Virgin Gorda and Anegada's lobster shacks are unmissable.

Sailing conditions: Trade winds 15–20 knots from the north-east. Fully sheltered in the Drake Channel. Suitable for beginners.

Best for: First-time Caribbean charterers, families, those wanting reliability and excellent infrastructure.

Costs: Bareboat 45ft catamaran from £3,500 per week (peak season). Add provisioning, mooring balls, customs and fuel.

Season: December to May. Hurricane season (June–November) — avoid.

The Grenadines

The case for: The chain of islands running from St Vincent south to Grenada is a step up in adventure from the BVI. The Tobago Cays Marine Park — five uninhabited islands encircled by the largest horseshoe reef in the Eastern Caribbean — is one of the finest snorkelling destinations on earth. Mustique brings private-island glamour. Bequia is the most charming sailing town in the Caribbean.

Sailing conditions: More exposed than the BVI. Open ocean passages between some islands, crossing the Atlantic swell. Not recommended for absolute beginners.

Best for: Experienced sailors looking for a genuine adventure with a more rugged, unspoilt feel. Fewer charter boats, more authentic village life.

Costs: Bareboat 40ft sailboat from £2,000 per week. Less infrastructure than the BVI means more provisioning planning required.

Season: December to May.

Martinique and Guadeloupe

The case for: French Caribbean at its most authentic. Martinique and Guadeloupe are French overseas territories — which means French supermarkets (remarkable provisioning), French cheese, French bread baked fresh every morning, and a culture entirely distinct from the Anglophone Caribbean. Le Marin in south Martinique is one of the Caribbean's largest charter bases. Guadeloupe's butterfly-shaped island offers extraordinary diversity — the rainforest peak of La Soufrière volcano to the east, flat coral beaches to the west.

Sailing conditions: Trade winds similar to the BVI. The passage between Martinique and Guadeloupe (past Dominica) can be bumpy. Strong local squalls in the lee of the islands — stay aware.

Best for: Sailors who want culture, gastronomy and scenery alongside the sailing. An underrated destination for repeat Caribbean charterers.

Costs: Bareboat catamaran from £2,000 per week. Lower prices than the BVI for comparable boats.

Saint Martin/Sint Maarten

The case for: The world's smallest land mass divided between two countries (French Saint Martin to the north, Dutch Sint Maarten to the south). The French side offers excellent provisioning and patisseries; the Dutch side offers duty-free shopping and casinos. The anchorage at Simpson Bay is a Caribbean institution. Maho Beach, where aircraft land over sunbathers' heads on final approach to Princess Juliana Airport, is one of the Caribbean's most surreal spectacles.

Sailing conditions: The passages from Saint Martin to Anguilla (north) or Saint Barths (south-east) are straightforward in settled trade wind conditions. The island provides excellent shelter in most anchorages.

Best for: Those who want a cosmopolitan base with good charter infrastructure and easy access to Saint Barths and Anguilla.

Costs: Bareboat 40ft sailboat from £1,800 per week. Strong competition between charter operators keeps prices competitive.

The Bahamas

The case for: A completely different sailing experience from the trade wind islands. The Exumas — a 120-mile chain of cays in the Great Bahama Bank — offer some of the most extraordinary water on the planet: crystal flats over white sand in water so shallow and clear you can see every starfish from the helm. The swimming pigs of Staniel Cay are a genuine natural wonder. The blue holes, the bonefishing and the emptiness are unlike anything in the Caribbean proper.

Sailing conditions: Lighter and more variable than the Eastern Caribbean trade winds. Strong currents in the ocean passages between the Bahamas and Florida. The Bahamas Bank is shallow — draft matters. A catamaran under 1.2m draft is strongly recommended.

Best for: Experienced sailors seeking a unique, off-the-beaten-track experience. Less established charter infrastructure than the BVI or Martinique.

Costs: Bareboat 45ft catamaran from £2,500 per week (US-based pricing). Provisioning expensive — stock up in Nassau before heading out into the Exumas.

Season: November to May. Summer hurricane risk significant.

US Virgin Islands

The case for: St Thomas (Charlotte Amalie) is one of the Caribbean's best provisioning and duty-free shopping centres. St John — two-thirds National Park — has some of the most spectacular snorkelling in the US Caribbean. Close proximity to the BVI (45 minutes by ferry) makes a US-BVI combination itinerary one of the great Caribbean cruises.

Best for: Those wanting the BVI experience with easy US formalities, duty-free provisioning and flights direct from major US hubs.

Costs: Comparable to the BVI.

A word on hurricane season

Do not charter in the Caribbean between June and November unless you are an experienced offshore sailor with appropriate insurance and a detailed hurricane preparedness plan. The statistics are not kind to recreational charter boats caught in a hurricane track.

The season runs approximately June 1st to November 30th, with peak risk in August and September. Some operators run discounted charters in early June and late November — approach these with caution and check hurricane tracking carefully.

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