We have often said, to really understand an island you must go out in a boat and look back. Boating and Islands just go together — to really see a place and know a place you must get away from it. It gives perspective to size, topography and foliage, and when you go to land, you really explore what makes an island tick. Just ask any pirate. The best part of any island are the hidden beaches, protected coves, tiny villages and little beach bars often unreachable other than by boat. There are countless special places only boaters know about and only boaters can get to, whether on a yacht, a sailboat or a pleasure boat. These are the best Caribbean islands for boating.
Bahamas
Because of its proximity to South Florida, it’s easy to take your boat here, whether on your own or with flotillas of boats — and once you get here, there are 700 islands to choose from, from the Abacos chain to Eleuthera to the Exumas. This is boating paradise. If you come here without a boat, you’re not seeing the whole Bahamas.
The British Virgin Islands
You might call it the sailing capital of the whole world. The winds are consistent and the distance between the islands makes this such an alluring destination, because you can island hop to your heart’s desire. That along with almost 100 bars you can take a dinghy to.
Grenada and St Vincent and the Grenadines
The Grenadines are what you dream about, from the color of the water to the Tobago Cays — this is paradise found by you on your boat. Grenada is a great launching point to enjoy the whole chain.
US Virgin Islands
St John is a great midway point between St Thomas and the BVI, and the island itself is a boater’s dream, with a host of hidden coves and private beaches you can only get to by water. There are also many uninhabited islands to explore and surrounding islands like Water Island.
Antigua
Antigua’s has been one of the Caribbean’s top sailing destinations for centuries, all the way back to Admiral Nelson. Today, it has the most prestigious sailing week in the Caribbean, it’s a great charter destination and its Falmouth Harbour is one of the world’s best Megayacht havens.
Guadeloupe
Perhaps the best-kept boating secret in the Caribbean, Guadeloupe has inhabited islands, all of which are full of delights for sailors, none more than the tiny archipelago-within-an-archipelago of Les Saintes. Charter a boat and explore the charms of the French West Indies.
St Martin/St Maarten
Two countries, one island, and an incredible boating destination, whether you want to moor off small French villages or explore the bustling beaches of Great Bay or even the Snoopy Island megayacht marina. Of course, then just take your dinghy to Pinel Island, with a population of zero people and two beach bars. And you can head to Anguilla for the day, or, if you’ re braver, St Barth.
Puerto Rico
This is the place for sportfishing, and it’s also a great stopping off point for people cruising through the Caribbean, whether you need a high-quality marina or are looking to head to Vieques and Culebra, the so-called Spanish Virgin Islands.
Turks and Caicos
You’ve got many islands in the vicinity of Providenciales, from Pine Cay to Salt Cay to Middle and North Caicos, and the diving and snorkeling are great, right off your boat.
Belize
This is a great place to charter a sailboat and simply go explore — from the beautiful beaches of Ambergris Caye to the 200-some islands and cays that dot the coast, like Moho Cay, above.
Grand Cayman
Based on its watersports and its diving (and its fishing) this is paradise for boaters who love the world beneath the sea.