A Guide to Sailing in the Caribbean

 Petit Bateau is a popular sailing spot in St Vincent and The Grenadines
Petit Bateau is a popular sailing spot in St Vincent and The Grenadines | © Jon Arnold Images Ltd / Alamy
Photo of Damien Gabet
25 November 2021

For many, the Caribbean is where sailing begins and ends. Why? Those magical trade winds for a start. Here blows year-round balminess for smooth light-of-sight sailing. Next, countless marine parks are the playground of discerning divers and wide-eyed snorkelers. Then there’s the panoply of historical harbours. Just take one look at Puerto’s Rico’s enchanting Viejo San Juan (Old San Juan) and you’ll see what we mean. Add the heady mix of cultures that underpin its wildly colourful cuisine and you begin to understand why the Caribbean remains destination number one for superlative sailing holidays.

Re-enact your own version of Pirates of the Caribbean by chartering a yacht for the day with SamBoat. Alternatively, hire a vessel for a full week through Dream Yacht Charter.

What to see and do

How to choose the best diving in this reef-riddled wonderland? Isolated Glover’s Atoll, off the coast of Belize and surrounded by a Unesco-listed marine reserve, has waters so clean and clear that coral grows to depths of 90m (295ft). Expect manta rays, bottlenose dolphins, sponges of fantastic variety and thriving populations of reef fish.

For the luxury-minded, the colonial town of Soufrière on Saint Lucia offers anchorages equal to their stunning surroundings. From the water, they’re backed by the jungled volcanic plugs of the island’s twin Piton peaks. Take your tender to feel the fine sands of Sugar Bay between your toes, or even to hike up the forested flanks of the Pitons.

Petit Piton seen from Soufriere in St Lucia | © robertharding / Alamy

Don’t miss the endless party vibe of the Jamaica International Invitational (JAMIN) Regatta, which lights up Montego Bay each December. And the fun’s not limited to the racing. Cocktail parties, live performances and perfect pimento-smoked jerk make this the right time to visit.

Best mooring locations

How often can you moor at a Unesco-listed Georgian-era marina? Nelson’s Dockyard in Antigua’s English Harbour was built in the 1740s and gets seriously lively during yachting week. Open to public boats since the 60s, it offers a chandlery, supermarket, bars, restaurants and berthing for over 40 boats, including two for superyachts. Contact through VHF10 or by calling +1 268-481- 5035/5033.

Head for the Unesco-listed Tobago Cays for a dreamy anchorage in clear waters shared with sea turtles and parrotfish.

The Green Sea Turtle is something of a symbol of the Caribbean | © John Insull / Alamy

In need of next-level seclusion? Set sail for boat-access-only North Sound Beach in the British Virgin Isles. If you see anyone in these sedate waters, it’ll probably be an A-lister. Or a turtle.

Where to eat and drink

Take New-World ingredients – chillies, potatoes and corn – add the freshest seafood and apply the culinary traditions of the Americas, Africa, India, China and Europe. Now there’s a recipe for serious diversity. No two islands eat the same in the Caribbean: Jamaica is the home of smoky, pimento-spiced jerk, while Puerto Rico roasts up some of the finest hog anywhere on earth.

You must visit upscale Le Tamarin on Saint Barths, a garden haven serving French/Caribbean dishes such as scallop carpaccio with citrus and seaweed.

For beachside local flavour, eat grilled fish, curry and roti at D’Coalpot on Tortola in the British Virgin Islands.

Best charter option

Dream Yacht Charter is a trusted agent throughout the Caribbean. They can arrange whatever you want – bareboating on sail-powered catamarans or powered monohull yachts to crewed charters and by the cabin deals for solo travellers. Alternatively, explore the waters of the Caribbean by chartering a vessel for the day through SamBoat. They team up with local boat owners to offer the best rental rates on small zippy motorboats, right up to gleaming skippered superyachts.

Where to get groceries

If you’re mooring at Nelson’s Dockyard Marina in Antigua, there’s a good-for-essentials minimarket on site. But for a bigger range and lower prices, just walk 500m (1,640ft) north along Dockyard Drive to The Covent Garden Supermarket. Open every day, it’s the best-stocked supermarket in English Harbour.

Superyachts and cruisers berthed in Nelson’s Dockyard Marina, Antigua | © Jim Monk / Alamy

Key annual sailing events

Outside June to September (peak hurricane season) the Caribbean offers more regattas than you could poke a paddle at. The Royal Ocean Racing Club’s Caribbean 600 takes in 11 islands over a 965km (600mi) circuit out of Antigua in February. It’s open to boats of all sizes and attracts the pros.

Climate and weather

Generally, December to April is best. Warm, moist trade winds and average minimum temperatures of between 23C and 25C and maximums between 27C and 30C are perennial. But June to November is hurricane season when many charter companies shut up shop. The weather can get squally even if you do miss a big one. The danger of hurricanes drops as you head further south, meaning islands such as Trinidad and Tobago are safest of all.

How to get there

Jamaica’s Sangster (Montego Bay), Puerto Rico’s Luis Muñoz Marín (San Juan) and the Dominican Republic’s Punta Cana are the most obvious international airports for entry. You can head to nearby ports of departure from each of these gateways, or fly to your port on Caribbean Airlines.

A view over Montego Bay in Jamaica | © lucky-photographer / Alamy

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