The Caribbean charter scene ranges from the glamorous anchorages of St. Barths and the British Virgin Islands to the quieter, untouched beauty of the Grenadines and the Exumas.
The high season, from December to April, brings reliable north-east trade winds, warm sunny days and the liveliest social scene - steady breezes also make it a wonderful season for sailing yachts. November and May offer lighter winds and a quieter alternative. Hurricane season runs from June to November, peaking in August and September with the year's strongest, most unpredictable winds, so captains typically avoid the region at its height, repositioning yachts further south or to the Mediterranean.
The Caribbean is a kaleidoscopic yacht route: from the vibrant bird sanctuaries of Barbuda to the volcanic drama of Saba. English Harbour and Nelson’s Dockyard breathe naval history, Saint Martin pairs French chic with Dutch flair, while Montserrat reveals a raw beauty shaped by its volcanic past. St Kitts & Nevis charm with colonial towns, St Eustatius keeps its quiet heritage, and Dog Island, Big Spring Cave and Little Bay uncover Anguilla’s wild, untouched side - all crowned by the glamour of St Barths, where luxury and sea merge in perfect harmony.
If you want to step away from the glitz and glamour and enjoy nature at its best, then Antigua`s little sister, Barbuda, is the perfect stop on your charter. After being destroyed by Hurricane Irma in 2017, where the entire population was evacuated to Antigua, the island is returning to its former self, and relies heavily on tourism. As the island is largely underdeveloped, it is the perfect habitat for hundreds of species of birds and animals. As Barbuda is composed of Limestone, it has amazing caves and sink holes for you to explore, if you can tear yourself away from the crystal clear waters & soft pink sand beaches.
Best for: nature, birdwatching, pink-sand beaches, snorkelling & seclusion
In the deep south of Antigua, English Harbour has carried its name since the 18th century when the Royal Navy set up its base on these balmy Caribbean shores. It is the epicenter of yachting in Antigua and home to Nelson's Dockyard, a UNESCO-listed site that captures the island's history with real atmosphere.
The old stores have become museums, shops and delightful restaurants - a perfect place to spend an afternoon exploring, sipping something special and gazing at the boats in the marina. Nearby, climb Shirley Heights for jaw-dropping views or relax at Pigeon Point and Galleon Beach. During Sailing Week, charter guests can join the lively ocean-centric fete.
Best for: history, sailing, views & regatta festivities
In the Leeward chain of the Caribbean Sea, close to St Martin lies Anguilla, which offers natural beauty and a more relaxed atmosphere, with the island generally less developed and one of the best kept secrets of the area. The locals have kept this pristine paradise from developers and Anguilla therefore attracts a high end clientele.
This Caribbean paradise is known for its ecologically important coral reefs, which are perfect for snorkeling, pristine palm lined beaches where you can enjoy a bbq and cocktail at one of the many vibrant beach bars, or anchor off one of the island`s quiet coves.
Best for: snorkelling, pristine beaches, beach bars & quiet anchorages
Steeped in history and the world's only working Georgian Dockyard, it's no wonder Nelson's Dockyard is a UNESCO wonder. Lovingly restored, this 18th century marina is pure magic and a welcoming gateway to Antigua's fabled folklore. Proud columns, warm stone, fascinating museums and impressive forts set the scene for exploration. Charter guests will fall in love with the period-style buildings and impressive ships. A decade of careful restoration brought the Dockyard back to its golden years - strolling here feels like walking through a living museum. Nearby you'll find plenty of dining, hiking trails in Nelson's Dockyard National Park and the scenic Shirley Heights for jaw-dropping views.
Best for: history, dining & scenic hikes
Montserrat is known for its active volcano which erupted and destroyed the island's capital, Plymouth, in 1995. There has since been an exclusion zone on the island, where thankfully, nature now flourishes and the landscape has completely transformed. A guided visit can be arranged to this carefully monitored area to learn more about this important part of the island's history.
Beaches on the island are rugged and feature the usual dark sand that volcanic islands are known for. Except one beach, Rendezvous Beach, which features pure white sands surrounded by lush green hills and the smoking volcano as a backdrop. A visit to Montserrat will certainly be a unique, once in a lifetime experience.
Best for: volcanology, unique landscapes & atmospheric photo sessions
St Kitts and its neighbouring island, Nevis are known for their historic, cultural and architectural importance. Despite relying heavily on tourism, the islands are less dense in hotel resorts and are amongst the most enchanting and picturesque in the entire Caribbean.
The preservation of their ecosystems is a paradise to nature lovers, and the gentle hike up Nevis Peak, the active volcano which makes up the island, will spoil you with amazing views. The capital of the islands is the bustling Basse-Terre, located on Saint Kitts where you can brush up on the island`s history at the National Museum or enjoy one of the many outdoor bars & duty free shopping.
Best for: history, culture, trekking & shopping
Delightfully named as the Caribbean`s hidden gem, Sint Eustatius was once one of the busiest seaports in the whole of the bright blue sea. This was where American and European colonies would turn to for exporting goods, especially as Sint Eustatius was a tax free haven owned by the Dutch. In the late 18th century, the French took hold and the ships all sailed away as heavy taxes were imposed.
Now, Sint Eustatius has a wild and organic vibe that has yet to be devoured by tourism. The beaches are narrow and volcanic and flanked by blue waters, the forests are tropical and laden with fruits, and there's old world forts to explore. Of course, there's plenty of snorkeling and beach combing and the chance to taste eclectic flavours in the island's eateries.
Best for: snorkeling, wild nature, historic forts & secluded beaches
A tiny island, Saba sits in the pocket of the West Indies that forms part of the Leeward Islands chain. This Dutch owned piece of heaven is called an unspoilt paradise. Abundant in marine life, studded by dramatic peaks, an oasis of green and blue, Saba Island has so much to offer for the nature lover.
A world class diving destination, Saba invites you to plunge beneath the surface and explore its kaleidoscopic colours. The whole coastline is a marine national park ensuring encounters with sea turtles, parrot fish, barracuda, and even whale sharks. Outside of the water there's rainforest trails, small museums, lace making workshops, and spa afternoons. For those exploring the Leeward Islands, Saba makes for a sensational stop.
Best for: diving, nature & spa
Believed to have earned its name from resembling a canine shape, Dog Island is just 6 miles out from the mainland of Anguilla. A private island of just over 500 acres, it lies just beyond Prickly Pear Cay and Seal Island, making it a great stop in the yacht charter chain.
Mangroves, cacti, sea grapes and prickly pear cloak the island in varying shades of flora, but what truly makes it stand out is the sky full of seabirds: over a hundred thousand pairs and 43 different species. Snorkelers around the protected marine park reefs may glimpse endangered turtles, including the Leatherback, the Hawksbill and the Green Sea Turtle. Bright white sands and turquoise seas set the scene for the ultimate beach experience.
Best for: birdwatching, snorkeling & secluded beaches
Anguilla is a vision of sleepy white sand beaches, swaying palms, and coconut kisses - but it is also steeped in history too. Big Spring is sure to ignite your fascination as you step back in time and discover a different side of island life. The Big Spring Cave is etched with prehistoric carvings that are believed to date back to Amerindian usage as far back as 600 AD. Once used as a water source, now the Big Spring is all dried up but still creates a cooling oasis thanks to the canopy of the rocks and trees. Oozing with mystical vibes, visiting the cave and seeing the petroglyphs adorning the walls is a must-have experience when visiting the island harbor area.
Best for: history & mystical atmosphere
On Anguilla’s northern shoreline lies a tiny gem - Little Bay with a silvery ribbon of sand dwarfed on either side by soaring golden cliffs and flanked by topaz waters.
This is one of Anguilla’s rare treasures: accessible only by boat, it’s free of crowds and any signs of civilization. Surrounded by coral and cliffs, the beach offers a chance to spot pelicans flying in and out of nearby caves. Those who love watching darting fish, marine life, and sea urchins can don a mask and spend hours exploring the shallows. The most adventurous can swim to the nearby rock - a popular spot for climbing and diving into the sparkling blue.
Best for: nature, secluded relaxation & snorkeling
St Barthélemy is named after Bartholomew, Christopher Columbus’s younger brother. It’s world‑renowned as a luxury charter destination. You’re sure to find the perfect beach here: there are over 20 to choose from along with excellent sailing opportunities.
This volcanic island is surrounded by shallow reefs, with its Capital Gustavia being home to the main harbour. Rich in corals and vulnerable habitats, the waters surrounding the island have been a protected area since 1996. Everything about the island is distinctively French despite belonging to Sweden for a good century. The island`s natural beauty seemlessly intertwines with the luxury resort vibe, lively nightlife and wonderful shopping and restaurants.Best for: beaches, nature & luxury getaway
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