Caribbean Sailing Charters

This stunning cruising ground is everything you would imagine and so much more. In the British Virgin Islands (BVIs), Caribbean sailing yacht charter guests can spend their days snorkelling vibrant coral reefs before visiting the famous Soggy Dollar Bar - known for its intoxicating Painkiller cocktail - for a night you’ll never forget.

Caribbean sailing charters

A sailing holiday in the Windward Islands makes for a bounty of wild experiences; allow the scent of exotic spice to enchant you as splash in Grenada’s crystal-clear waters, or discover real island living in Barbados.

In the Leeward Islands, St Kitts promises rugged adventure while Caribbean sailing holidays to Antigua offer a chic escape complete with Michelin-Star cuisine. The unspoiled Grenadines are the place to come if you seek undisturbed relaxation, the most untouched of all the Caribbean island groups.

Oyster offers sailing yacht charters exploring every one of these blissful regions. Read on to learn more.


The best time to visit the Caribbean by sailing yacht charter is between December and April. Although the region is known for having a permanently glorious climate, averaging between 24-29°C/75.2-84.2°F all year round, a visit during these months offers lower humidity and less chance of rainfall. It also falls outside of the June-November hurricane season. You can expect temperatures of around 26°C/78.8°F and blissfully calm waters, perfect for bathing away your troubles or getting your heart racing with some exhilarating watersports.

Some of the most popular times for crewed Caribbean sailing yacht charters include the Christmas and New Year’s period and the Easter weekend when the islands fill up with festivities. You will discover more secluded sailing destinations and deserted beaches outside of these peak holidays, but the festive magic is hard to beat. The choice is yours...

Maximising your island-hopping experience onboard a Carribean sailing yacht charter allows you to explore every little bay that takes your fancy. Drop anchor by tiny secluded coves and discover deserted islands where you really can get away from it all.

For skippered Caribbean sailing holidays, look no further than Oyster. Our beautiful boats are light and spacious with luxurious furnishings that prioritise comfort without compromising on practicality. Large windows below decks mean you’ll be able to spot every single palm tree that dots the horizon, while our highly-professional crew come equipped with a local’s knowledge of every part of the Caribbean.

Explore this stunning region on one of our luxury sailing yachts, or read on to learn about sailing the beautiful island groups of the Caribbean.

Sailing in the British Virgin Islands

An iconic cruising ground for Carribean sailing holidays, the BVIs are not to be missed. With nightlife that will have you dancing until dawn, seafood restaurants with fresh tuna and gin-clear waters offering perfect conditions for snorkelling and diving, this is the epitome of island living. Sail out to the caves at Norman Island to swim amongst exotic sea life and marvel at the vibrant colours. For charter guests who want nothing more than to lie on the sand and relax, cruise over to Anguilla, where the island’s flat topography makes for some truly phenomenal beaches. As the sun begins to set, head to The Rum Bar at Cooper Island, or for those who want to party all night, why not hop between the many lively bars on Jost Van Dyke.

The BVIs provide a delightful climate throughout the peak charter season: a perfect escape from the colder weather of the Northern Hemisphere.

Sailing in the Windward Islands

The Windward Islands deliver surprise after surprise on any Carribean sailing holiday, with each island full of its own unique character. St Lucia promises a vibrant history and rugged landscape - hike the Pitons for some truly incredible views across the islands and out to sea. Bequia is considered by some as the perfect Caribbean island, its difficult to get to by aeroplane meaning it has been protected from mass tourism, preserving all of its natural beauty. Glamourous Mustique is the favourite holiday spot of A-List celebrities and supermodels. However, despite its famous visitors, this three-mile haven is surprisingly low-key, with only one (extremely elegant) hotel on the island.

Authentic Caribbean living and jaw-dropping natural beauty await in the Grenadines - a 35-island region that lies within the Windwards. Snorkel in the Tobago Cays to meet friendly marine turtles and revel in the untouched landscape. Head to Mayreau for the wild nightlife and swim at best-kept-secret beach Salt Whistle Bay. Try your hand at kiteboarding on Union Island, and hang out with the locals in this laid-back set of villages. Caribbean sailing yacht charterers will love the variety of experiences that await in this cruising ground.

Head to the Windward Islands from December through to April to experience them at their best, with a multitude of fantastic events across all the islands. Look out for the Barbados Film Festival, now in its third edition and normally held in late January, or the lively Carriacou Carnival in mid-February. Also, visit in February to experience the yearly St. Vincent Yacht Club Regatta, or in March for the Saint Vincent’s Blues and Rhythms Festival.

Sailing in the Leeward islands

The Leeward Islands are famous for their good sailing winds, making them a must-visit destination for experienced sailors or those on skippered Caribbean sailing holidays, where the crew will guide your vessel while you simply relax. Head to Antigua, one of the most important superyacht hubs in the Caribbean, for unmatched glamour and a rich history. Don’t leave without touring Nelson’s Dockyard, the preserved 18th-century base of the British Fleet in the West Indies.

As the smallest landmass ever to be divided between two nations, St Martin/St Maarten offers a chance to experience both French and Dutch culture while revelling in the island’s majestic green peaks and crystal-clear waters. Heavenly St Barts has not one but fourteen gorgeous beaches at which to stretch out and do nothing or to get your pulse racing with some exhilarating water sports. Meanwhile, on St Kitts and Nevis, lose yourself in sugar plantation history at the UNESCO-protected Brimstone Hill Fortress National Park. This is an island group for those with an adventurous spirit, but it wouldn’t be a Caribbean sailing yacht charter destination without also being packed full of amazing beaches upon which you can soak up the sun.

In peak sailing season, the Leeward Islands offer the lowest humidity of all the Caribbean islands - perfect for keeping cool during those more challenging hikes - and temperatures average between 27°C/81°F and 35°C/95°F, ideal for lazy days on the beach.

Learn more about how to charter a sailing yacht in the Caribbean with Oyster. Discover Oyster luxury sailing yachts for charter or contact Oyster Charter Manager, Fiona McCarthy to begin planning your trip.