The best time to visit the Caribbean depends on how hot you want the weather and if you want to escape the crowds. The sailing season in the Caribbean peaks February to April and in December, particularly over Christmas and the New Year. The mid season is January, May to June and November. The low season is July to October.


If you love watersports, you’ll find the best snorkelling and paddle boarding in the Caribbean. Read our blog, What’s SUP? What water toys do you need for your yacht charter? or find out about the exotic wildlife in our blog The creatures you’ll encounter on your Caribbean adventure. If you’re sailing with beginners then the Caribbean is a great destination choice, check out our guide Sailing with first timers.


Antigua sailing can include itinerary highlights such as St. Kitts, Nevis, Montserrat and Guadeloupe. Don’t forget the Caribbean’s most exciting event in the racing calendar, Antigua Sailing Week. Sail lively Jolly Harbour, snorkel in North Sound, relax on beautiful beaches at Dickenson Bay or wander around Nelson’s English Harbour.


Charter a yacht in the Bahamas and discover the coral reef across two impressive island chains, the Exumas from Nassau or Abacos from Marsh Harbour. Enjoy shallow waters in the Abacos, perfect for catamarans, and hop between Tahiti Beach on Elbow Cay, Man O’ War Cay, explore pirate history on Green Turtle Cay and drink at Nipper’s Bar on Great Guana Cay.


Discover the world’s second largest barrier reef in Belize, a Caribbean sailing bucket list destination for those who love diving, snorkelling and swimming. Hundreds of cays are ripe for exploring, including South Water Cay’s barrier reef drop off, Tobacco Cay’s turtles and Queen Cay’s beaches. Or hop ashore for the wildlife on Monkey River, uncover ancient Mayan history and tour the staggering cave network.


Sail the British Virgin Islands’ cays and islets and enjoy lobster on Anegada, the Baths on Virgin Gorda’s, Jost Van Dyke’s Painkiller punch and the relaxed vibe in some of the Caribbean’s most famous sailor bars. If you are planning a yacht charter in the BVIs, read our blog First time sailing bareboat in the BVI – 1 week itinerary. For ideas on where to eat out in the BVIs, read LateSail sailor reviews BVI dining post-Irma. For BVI marina fees, cruising tax and national park costs, provisioning advice and BVI sailing conditions, read the LateSail BVI Charter Guide.


A catamaran charter in St. Martin has a special place in the hearts of Caribbean sailing fans. Enjoy gentle sailing and stop offs at Grand Case’s bars, boutiques on St. Barts, St. Kitts’ historical port, Nevis’ Fort Charles, the restaurants at Gustavia and the waterfront at St. Eustatius.


Explore the Virgin Islands National park on St. John with a bareboat yacht charter in the US Virgin Islands. Snorkel Buck Island with its coral reefs and turtles off St. Croix, or enjoy the beaches on St, Thomas, including Lindquist Beach, Lindbergh Bay and Brewer’s Bay.


Get to know the ‘Galapagos of the Caribbean’, the archipelago of Jardines de la Reina, with a catamaran charter in Cuba, just 60 miles off the coast. Sail the marine reserve and uninhabited Cayo Blanco, known for its amazing diving, and Cayo Bretón. You’ll find mangrove islands, pillar coral, sponges, plenty of tropical fish, nurse sharks, American crocodiles and turtles. Or head to the Canarreos archipelago where the coral is thriving.


Plan your Caribbean yacht charter experience from Grenada, St. Lucia, Martinique and St. Vincent to explore the Grenadines and its chain of exciting islands, including Carriacou, Petit St. Vincent and Union. Sail Mayreau’s romantic Salt Whistle Bay and the glorious archipelago of Tobago Cays with its five islets and marine park with some of the best snorkelling in the Caribbean. Dive the Bat Cave and Anchor Reef on St. Vincent, mingle with the jet set on Mustique or go turtle watching on Bequia.


Sail a catamaran in Guadeloupe and explore the magical underwater world of Jacques Cousteau on Pigeon Island, a Caribbean diving paradise. Snorkel at Gosier Islet’s shipwreck, taste the rum on Marie-Galente, hike Dominica’s national park and cruise Les Saintes archipelago. Make time to stroll the volcanic landscape of Basse-Terre and Grande-Terre’s fantastic sandy beaches.

Across the water from the BVIs, you’ll find an authentic Caribbean sailing experience in Puerto Rico. Snorkel Culebra’s Flamenco beach, explore wildlife on the coral island of Culebrita and Isla de Vieques, kayak Ensenada Honda’s mangroves and sail the 12 islands in La Cordillera nature reserve, off the Fajardo coast.

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