The Caribbean

Yacht expeditions > Destinations > The Caribbean

Beyond the white-sand good looks

One-off carnivals in Cuba, remote sandbar beach parties and submersible dives – we take Caribbean charters to the next level. Think multi-helicopter and support yachts, providing special access.

Expect everything from volcanic heli tours in Montserrat and rum tastings in privatised heritage distilleries to joining pro crews for a private regatta in Antigua and monitoring ray habitats with conservationists in the Bahamas. We’ve also got the contacts to permit special destinations, including among Cuba’s diverse European charms.

Wherever your interests lie, we’ll put together a route that matches your group’s passions – focused on less-touristed anchorages and hard-to-access destinations. Often that also means bringing in experts, whether that’s a championship-winning windsurfer or a marine biologist to bring your dives to life.

Featuring imagery taken on Cookson Adventures trips

We’re always aware of how precious our client’s down time is. They don’t need more stuff. The luxury is time outside of their normal life. Time with their partner and their children. Our goal is always to maximise the quality of this time. That is why we also love to incorporate yachts into our adventures, as you travel in a bubble of comfort that you are familiar with but then you can dip into different places and explore further.

Henry Cookson on Cookson Adventures May, 2025

Special setups

We organise gourmet setups around your tastes – masseuse tents on white sands, a private-chef barbecue with your fresh catch or even a full banquet, paired with live jazz. We’ll scout out the best locations, whether a remote lagoon to efoil from or a pristine, undisturbed sandbar for the ultimate in relaxation.

Hands on conservation

Go behind the scenes of non-profits that have re-introduced manatees into the Dominican Republic. Join researchers in sampling coral reefs in Turks and Caicos. And lend a hand in monitoring shark nursery areas with international conservation organisations.

Underwater adventure

Perhaps learn to freedive with yogi-taught breathing techniques, before getting up close to playful turtles undisturbed by bubbles. Or, dive with rays and mantas – we know the best spots.

Experts

A marine archaeologist to bring Les Saintes’ historic wrecks to life, championship-winning sailors to show you the ropes or top actors to create an immersive treasure hunt for your family – we’ll bring in the experts to bring your trip to the next level.

We know how to get the most out of the Caribbean. With short sailing distances, multi-island itineraries are perfectly smooth and offer surprising diversity – from chic St. Barts to volcanic Guadeloupe. We can also see you enjoy special access to the region’s celebrated calendar of events, such as New Year’s Eve in Gustavia or Antigua Sailing Week.

Here’s a few sample experiences in different destinations:

Windward Isles – amongst lush, rugged landscapes and richer trade winds, swim with majestic sperm whales in Dominica, let an authored historian take you around Martinique’s 17th-century forts or kitesurf with pros in St. Vincent and the Grenadines. There are also anchorages among St. Lucia’s iconic, green-carpeted Pitons.

Cuba, Dominican Republic & Jamaica – let us open up Cuba’s historic charms, having permitted superyacht trips here alongside private festivals and after-hours access to museums. Then, enjoy exclusive access to Jamaica’s historic music studios and coffee estates alike, while our heli trips in the Dominican Republic bring you to private musical performances held in petroglyph-dotted caves.

Belize & Honduras – whether soaring over Belize’s iconic Blue Hole in helis or diving among its black-tip sharks, we’ve explored this pristine region extensively. Honduras’s Bay of Islands, too, rewards with pristine beauty, and the chance to get involved with turtle tagging and reef surveys alongside conservationists.

Cayman Islands – there’s plenty of icons here, from swimming with stingrays and relaxing on Seven Mile Beach’s pristine sands to WWII wreck dives in year-round clear waters.

Virgin Islands – learn about the Caribbean’s piratical past with an immersive, actor-led treasure hunt spanning multiple islands with cryptic clues. Rock pools, swims with spotted eagle rays and vibey beach bears add to the intrigue.

The Bahamas and Exumas – we’ve brought guests to dive among sharks, swim with pigs and contribute to biologist-led reef work. We can also see you access James Bond’s stunning Thunderball Grotto after hours and swim with nurse sharks at Compass Cay.