Sailing charters have seen a resurgence as more holidaymakers than ever want to reduce the environmental impact they have on the places they visit, and the Caribbean is one of the prime places to roam the seas in style. Leave the fast lane for an in-depth look at the amazing animals in environments that range from dense rainforest to coral-covered shipwrecks and be sure to pause on the powdery-soft white beaches for some well-earned rest in the sunshine.

When it comes to selecting a sailing yacht there is everything from the ambiance of a large traditional vessel to the modern luxuries and intimacy of a contemporary catamaran to suit your family group.

Wake up at your destination and be the first to explore landmarks before the crowds arrive – or be the last to leave when you have your accommodation and meals ready and waiting for your return. Best of all, your expert chef will create a variety of mouth-watering meals and the rest of the professional crew will keep adults and children alike entertained with hours of water sports.

In the vast Caribbean cruising grounds here are five destinations to consider for their attractions and favourable winds.

The British Virgin Islands

A favourite holiday destination in the Caribbean, the British Virgin Islands is easy cruising from one glorious beach to the next. You will be surrounded by gorgeous crescent beaches the moment you fly in but a short cruise over to Virgin Gorda will take you to The Baths, famed for its circular boulders and fantastic snorkelling in the shallows. The Dog Islands are a great place to dive for beginners and experienced guests alike, after which the group can stretch out on the sands and dine outdoors as the sun sinks over the horizon.

Dance the night away at the famous Foxy’s Bar and the Soggy Dollar Bar on Jost Van Dyke then wake up to the tranquil shores of Peter Island before diving the wreck of the R.M.S. RHONE, one of the most visited wrecks in the Caribbean. Sail back to Tortola for shopping, art and historic sites such as Smuggler’s Cove and the family-owned Callwood Rum Distillery, where they still use the same 400 year-old equipment.

St. Vincent & the Grenadines to Grenada

Travel through St. Vincent and the Grenadines and witness the incredible wildlife that migrates through this region as you kayak, snorkel or Scuba dive: The Tobago Cays marine reserve is filled with colourful fish and thriving corals, and dolphins, whales and turtles regularly pass through the region.

Only nine of the 32 islands in the Grenadines are inhabited, leaving the rest for you to discover for yourselves. Fort Charlotte was a filming location for The Pirates of the Caribbean and the volcanic beauty of the black sand beaches, La Soufrie Volcano and the Dark View Falls will make for breath-taking backdrops to your family photos. Bequia has great Scuba diving and snorkelling sites and Grenada, the Island of Spice offers the finest fresh ingredients for an unforgettable mouth-watering meal. End a perfect day on your sundeck over drinks and conversation with close friends and family in the fresh open air.


Basse-Terre, Grande-Terre, La Désirade, Les Saintes and Marie-Galante make up the five picturesque islands of Guadeloupe where soft sand beaches lead to waterfalls hidden within verdant rainforests. Marie-Galante produces some of the Caribbean’s best rum and you can stock up before sailing off to the uninhabited islands to have your own beach party under the stars.

The Jacques Cousteau Underwater Park is unmissable for its beautiful corals and spectacular wildlife where you can spot humpback whales and turtles. Use the trade winds to travel between your destinations and power on board water toys such as sailing dinghies, windsurfers and kite surfers, or simply lie back and savour the warm breeze.

St. Barthelemy

For sailing groups who want the perfect balance between nature and the luxuries of civilisation, St. Barthelemy is a classic destination filled with world-class restaurants, stylish boutiques and art galleries. The shallow beaches around Gustavia Port are ideal for families with young children and there are plenty of snorkelling and Scuba diving sites. Sailing yacht enthusiasts can witness some of the world’s highest performing sailing yachts compete in the yearly St. Barth’s Bucket before disappearing into the surrounding Saint Barthelemy Natural Reserves for complete peace and quiet away from the crowds.


Named ‘one of the world’s top countries for travel in 2020’ by Lonely Planet, Aruba is a year-round destination where there is a steady six knots of wind perfect for sailing yachts and wind-based water sports. Cruise from one white-sand beach to the next and delight in the incredible artificial reefs created from wrecks that both snorkelers and beginner Scuba divers can reach in the shallows. Kayakers and paddleboarders can observe sea turtles pass by through the crystal clear waters surrounding Mangel Halto while the sheltered lagoon at Arashi Beach is home to myriad colourful fish.

Concerts, festivals and exhibitions take place throughout the year across the island with a choice selection of events in Oranjestad: The Soul Beach Music Festival is a multi-day extravaganza and the Aruba Art Fair showcases the talents of local and international artists.

Across the other side of the island tracks lead away from the coast into the Arikok National Park, where your group might spot the endemic Aruban Burrowing Owl or the swift hummingbirds flitting between flowering cacti. The bountiful waters are excellent for sport fishing and mahi mahi, wahoo and tuna are among the many desirable species that could be delivered from your fishing line to your plate.

Sailing in the Caribbean offers that chance for adventure and leisure in equal measure with the unbeatable benefits to having your accommodation, entertainment and skilled crew at your service wherever you travel.

Trina Howes is a Director of CharterWorld America. CharterWorld is a luxury private yacht charter company that creates outstanding vacations with excellent yachts at amazing prices – worldwide.

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