The Best Places for Island Hopping in the Caribbean — From the BVI to the Bahamas
There’s something about island hopping in the Caribbean that feels like pure freedom. It’s the ease of waking up on one island, slipping onto a boat, and finding yourself somewhere entirely different by lunchtime. The air shifts. The sand feels new. The water looks the same but never really is. It’s part of the Caribbean fantasy that drives all of us.
This is a region built for movement. Ferries, water taxis, short hops and private charters make it easy to move between places that are close in distance but completely different in character. One day might mean barefoot lunches on an empty cay. The next could be sundowners in a historic harbor. These are the best places in the Caribbean to make the sea your itinerary.
Think of all these places as the perfect jumping off points for your island-hopping imagination. Each one is its own Caribbean universe, with an infinite number of vacation permutations.
British Virgin Islands
The British Virgin Islands are often called the sailing capital of the Caribbean — and for good reason. This archipelago was made for moving between islands. Tortola is the anchor, home to marinas and ferry terminals that make exploring effortless. A short sail or ferry ride takes you to Virgin Gorda and its famous natural boulders and beaches, or to Jost Van Dyke with its iconic barefoot beach bars and easygoing energy.
But the magic is in the details. Norman Island, long whispered about as the inspiration for Treasure Island, offers hidden coves and quiet anchorages. Cooper Island has its own eco-chic vibe with calm waters perfect for swimming and snorkeling. Scrub Island is refined and elegant, a stop for those who like their island hopping with a touch of polish. And then there’s Anegada, low, flat and wonderfully remote — a world away from the hills of Tortola. All of these islands are close enough to visit on the same trip, yet each feels entirely different. And yes, you can also explore all of the nearby USVI with ferries, too.
Karen Udler is the Deputy Travel Editor of Caribbean Journal. A graduate of Duke University, has been traveling across the Americas for three decades. First an expert on Latin American travel, Karen has been traveling with CJ for more than a decade. She likes to focus on wellness, luxury travel and food.
