A Guide To Sailing In The Caribbean

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.

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.

Petit Piton seen from Soufriere in St Lucia

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

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.

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

Key annual sailing events

Outside June to September (peak hurricane season) the Caribbean offers more regattas than you could poke a paddle at.

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.

Did you know – Culture Trip now does bookable, small-group trips? Pick from authentic, immersive Epic Trips, compact and action-packed Mini Trips and sparkling, expansive Sailing Trips.

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.