The Caribbean is a dream for sailors. Warm trade winds, line-of-sight navigation and hundreds of anchorages make it perfect for both first-timers and experienced skippers. From chic islands with designer boutiques to wild anchorages where turtles glide under your hull, there is a route for every style and budget. This guide highlights eight of the best Caribbean sailing destinations, from classic one-week itineraries to longer island-hopping adventures. You will find ideas for families, couples and groups of friends, plus links to help you plan your next charter with Click&Boat.
1. British Virgin Islands (BVI)
The British Virgin Islands are often called the sailing capital of the Caribbean. Short distances, steady trade winds and well-protected bays make the BVI ideal for a first charter. Hop from Norman Island to Jost Van Dyke, snorkel at The Indians and anchor off the famous Willy T. There is a wide choice of marinas, mooring buoys and beach bars, so logistics stay easy and fun. To plan a route and see what to expect, check out our detailed guide to a BVI sailing vacation.
2. Saint Martin, Anguilla and Saint Barth
This trio of islands mixes French flair, Dutch efficiency and laid-back Caribbean charm. Start in Saint Martin, a great base with marinas, provisioning and many charter options. From there you can sail to quiet coves in Anguilla or drop anchor off the chic beaches of Saint Barth. The sailing is varied, with short hops and a few livelier crossings that reward you with turquoise bays and soft sand. A catamaran is perfect here for comfort and space.
3. Antigua and Barbuda
With “a beach for every day of the year”, Antigua and Barbuda are a paradise for sailors who love long stretches of sand. Historic English Harbour and Nelson’s Dockyard provide a beautiful, sheltered base with real maritime character. From there you can explore Half Moon Bay, Green Island and the quiet anchorages off Barbuda’s pink-tinged beaches. Trade winds are reliable and there is good protection behind surrounding reefs. Whether you enjoy regatta vibes or relaxed cruising, Antigua works for both.
4. The Grenadines
The Grenadines feel like the Caribbean of postcards: small, low-key islands scattered in bright turquoise water. Sail from Saint Vincent down to Bequia, Mustique and Canouan, then continue to the famous Tobago Cays, where turtles graze on the sea grass around your boat. Anchorages are often set behind coral reefs, giving calm, clear lagoons that are ideal for snorkeling. Distances are short but you still feel pleasantly far from mass tourism. The Grenadines are perfect for sailors who want an authentic, slightly wilder atmosphere and do not mind a bit more breeze and open-water sailing between islands.
5. Saint Lucia
Saint Lucia is known for the majestic Pitons that rise straight from the sea, creating one of the most dramatic anchorages in the Caribbean. Many itineraries combine Saint Lucia with the Grenadines, but the island itself already offers a lot. You can anchor in Rodney Bay, explore quiet coves down the west coast and spend a night under the Pitons at Soufrière. On shore, there are hot springs, rainforests and viewpoints to explore. Saint Lucia works well for couples and groups who like a mix of sailing, hiking and local culture, with slightly more lively nightlife than smaller islands.
6. Martinique
Martinique is a fantastic starting point for a Caribbean sailing holiday thanks to its modern marinas, good flight connections and French-Caribbean culture. The south coast offers many sheltered bays such as Le Marin, Sainte-Anne and Les Anses d’Arlet, all linked by easy day sails. You can snorkel with turtles, enjoy creole cuisine and, if you have more time, sail further south towards Saint Lucia and the Grenadines. The island suits both beginners and more experienced crews.
7. Guadeloupe
Guadeloupe is shaped like a butterfly, with mountainous Basse-Terre on one side and beach-rich Grande-Terre on the other. It is a great base for a varied cruise that combines rainforest hikes, waterfalls and relaxed anchorages. Many sailors set course for the nearby archipelago of Les Saintes, famous for its sheltered bay, colorful village and panoramic viewpoints. You can also include Marie-Galante for quieter anchorages and wide sandy beaches. Distances stay short, but each stop feels different. Guadeloupe is perfect if you want a mix of French influence, local Caribbean life and flexible itineraries for one or two weeks.
8. The Bahamas
Although technically in the Atlantic, the Bahamas are often included in Caribbean sailing dreams. With hundreds of cays and sandbars, they offer shallow, clear waters that are ideal for catamarans and families. The Exumas are particularly popular, with blue holes, sandbanks and famous Pig Beach. For timing your cruise, see our guide to the best time to sail to the Bahamas. If swimming with the pigs is on your bucket list, learn more about swimming with pigs in the Bahamas and plan a stop at Big Major Cay.
FAQ
The main season runs from December to April, with steady trade winds and little rain. Hurricane season generally lasts from June to November.
The BVI, Martinique and the Bahamas are ideal for first-time sailors thanks to short hops, good shelter and clear navigation.
It depends on the country and the type of boat. In many places a good sailing résumé is enough, but always check local rules and charter requirements.
One week is ideal for a first itinerary around a single island group. Ten days or two weeks give you time to combine several islands at a relaxed pace.
