Best Sailing Spots In The Caribbean

sailing boat

We have always said, to truly understand an island you have to go out in a boat as well as look back. Islands and Boating just go together — to see a place and really know it, you have to get away from it. It provides perspective on topography, foliage, and size and when you go to land, you explore what makes the island tick. Ask any pirate. Now, the best part of an island are the protected coves, hidden beaches, tiny villages and beach bars regularly unreachable other than via boat. Therefore countless unique places that only boaters know and are the only ones that can get to, whether on a Caribbean yacht charter, a pleasure boat or a sailboat. These are the best sailing spots in the Caribbean islands for boating.

The British Virgin Islands

Now you may call it the entire world sailing capital. The winds are really consistent, and the distance of the islands makes it such an alluring spot since you can island hop to suit your heart’s desire. That together with nearly 100 bars you could take a dinghy.


Due to its closeness to South Florida, it is easy to take a boat here, whether with flotillas of boats or you are on your own — and as soon as you get here, there're 700 islands to select from, starting from the Abacos chain to the Exumas to Eleuthera. This is sailing paradise. Now if you come without a boat here, you do not see the entire Bahamas.

United State Virgin Islands

St John is a good midway point between the BVI and St Thomas, and the island is the dream of a boater, with a host of private beaches and hidden coves, you can only reach by water. Also, there are a lot of uninhabited islands for you to explore and even surrounding islands such as Water Island.


It has been among the top Caribbean sailing spots for centuries now, all the way to Admiral Nelson. Right now, it has the most prestigious Caribbean's sailing week, it is a great charter spot, and the Falmouth Harbour is among the best Megayacht havens in the world.


Perhaps one of the best-kept secrets of Caribbean's boating, Guadeloupe has many inhabited islands, which are all full of delights for its sailors, none above the tiny archipelago-in-a-Les Saintes archipelago. Charter a boat and get to explore the French West Indies charms.

St Martin/St Maarten

One island, two countries, and an amazing boating spot, whether you would like to moor off French villages or just explore the lively beaches of Great Bay or the Snoopy megayacht marina Island. Of course, then take the dinghy to Pinel Island, having a population of zero persons and two beach bars.

Puerto Rico

This is the spot for sportfishing, and it is also an amazing stopping off point for those cruising via the Caribbean, whether you're in need of top quality marina or are just looking to go to Culebra and Vieques, the Spanish Virgin Islands as it's called.

Grand Cayman

Depending on its watersports as well as its diving, this is paradise for a lot of boaters who are in love of the world beneath the sea.


All in all, if you are a sailing enthusiast and decide to visit the Caribbean Islands you cannot really go wrong, wherever you go it is the right decision because the Caribbean Islands are full of extraordinary and beautiful things that are just waiting to be explored. Sailing in the Caribbean is a no-brainer and it I highly recommend it.

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