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.
U.S. Virgin Islands
St Thomas, St John and St Croix (along with places like Water Island and Buck Island) make up one of the most accessible island-hopping regions in the Caribbean. St Thomas has the busy harbor, historic streets and flight connections. St John offers a softer, quieter feel, with national park beaches and waters that seem untouched. St Croix is larger and more laid back, where sugar mill ruins meet protected reefs — and a buzzing food scene.
What makes this region special is how easily it extends into the British Virgin Islands. From St Thomas, ferries and charter boats can have you in Tortola in under an hour. From there, Virgin Gorda, Jost Van Dyke, Norman Island and Anegada are all within easy reach. It’s a rare itinerary that lets travelers move between two territories, shifting seamlessly between cultures and landscapes.
Grenada and the Grenadines
Grenada is the starting point for one of the Caribbean’s most magical chains of islands. The main island itself is vibrant and full of natural beauty, but just off its northern coast, Carriacou waits — a small, friendly island with beaches you can walk to in minutes and waters perfect for sailing. Petite Martinique is even quieter, a place where time seems to have its own pace. White Island and Sandy Island offer the opposite of bustle — these are places you arrive at by boat and often find entirely to yourself.
Continue north and the Grenadines open like a string of pearls: Union Island with its little harbor and restaurants right on the water, Palm Island and Petit St Vincent with their private-island serenity, Canouan with its luxe calm, Bequia with its village charm. And at the center of it all, Tobago Cays — a protected marine park where turtles swim alongside sailboats. Island hopping here feels like gliding through a living postcard.
Guadeloupe
Guadeloupe is one French Caribbean department but many islands, tied together by short rides and shared culture. Grande-Terre and Basse-Terre form the heart — connected by bridges, yet distinct in mood. Grande-Terre is bright and breezy, while Basse-Terre is wild and lush, with waterfalls and volcanic peaks. But the true joy of Guadeloupe is how easy it is to leave the main islands and set off.
A short ferry takes you to Les Saintes, a tiny archipelago with cobblestone lanes, quiet harbors and a distinctly French-Caribbean charm. Marie-Galante lies just beyond, a wide, gentle island with sugarcane fields and long beaches that feel almost secret. La Désirade is even quieter — a place of long horizons and few crowds. Together, these islands create an itinerary that’s intimate, connected and full of character.
Abaco
The Abacos feel like their own world. This string of islands and cays in the northern Bahamas is built for wandering — by ferry, small plane, or your own boat. Great Abaco and Little Abaco anchor the region, but the real magic happens as you hop to places like Green Turtle Cay, Hope Town on Elbow Cay, Man-O-War Cay and Great Guana Cay. Each has its own identity: Green Turtle’s timeless village charm, Hope Town’s candy-colored harbor, Guana Cay’s lively beach bars.
Sailing here feels effortless. The waters are calm, the islands are close, and there’s a kind of quiet rhythm to the days — moving between small harbors, secluded beaches and tiny settlements where the welcome always feels personal. Abaco isn’t just a destination; it’s an archipelago built for exploring slowly. And then there’s that Abaco blue.
Exuma
If the Abacos are classic sailing country, Exuma is pure escape. Stretching south from Nassau, the Exuma chain is a ribbon of more than 350 islands and cays, each a shade of turquoise that seems impossible to describe. Great Exuma and Little Exuma form the main hub, where travelers base themselves before setting out.
From there, the Exuma Cays unfold in every direction. Staniel Cay brings postcard-perfect harbors and the famous swimming pigs. Big Major Cay, Compass Cay and Norman’s Cay each offer their own wild beauty. Many of the cays are uninhabited, which makes island hopping here feel like a private adventure — a journey between sandbars, clear water and hidden beaches that belong to no one in particular. Exuma is the kind of place where every short hop feels like entering a new world.
St Maarten
St Maarten might be small, but it’s one of the Caribbean’s greatest island-hopping hubs. Daily ferries and quick flights connect it to St Barth, Anguilla, Saba and Statia — each an entirely different world. St Barth is polished and glamorous, a place of chic beach clubs and French patisseries. Anguilla is quiet and soulful, defined by its soft beaches and calm bays.
Saba rises dramatically out of the sea, a volcanic peak with rainforest hikes, winding roads and an almost untouched feeling. Statia, or St Eustatius, carries a rich colonial history and the kind of authenticity that’s rare and compelling. You can easily touch all four of these islands in a single week — a journey that moves from luxury to history to wild nature, with St Maarten’s busy harbor as your home base.
St Vincent and the Grenadines
St Vincent and the Grenadines is an archipelago built for slow, beautiful travel. St Vincent is the gateway, green and mountainous, but most travelers quickly find themselves heading to Bequia — an island that still feels personal, full of local shops, harborside restaurants and soft beaches. A little further south, Mustique has its own mystique, a private island with a storied past and a polished, understated feel.
Canouan brings quiet luxury, while Palm Island and Petit St Vincent feel almost dreamlike in their seclusion. Tobago Cays lies at the center of it all, a national marine park that’s one of the most beautiful anchorages in the Caribbean. Here, hopping between islands isn’t just easy — it’s the way this place is meant to be experienced.
Puerto Rico
Puerto Rico offers one of the most flexible and rewarding island-hopping itineraries in the Caribbean. Start in San Juan, with its historic streets and vibrant culture, then head east to Vieques. There, you’ll find wild beaches and the famous bioluminescent bay. Culebra is next — quieter, smaller, home to Flamenco Beach, one of the most spectacular stretches of sand in the region.
From there, it’s easy to jump to St Thomas or St Croix in the U.S. Virgin Islands, or even on to the BVI. This is a rare circuit where ferries, water taxis and short flights all work together seamlessly. One trip can blend city, wilderness, history and quiet island life.
Turks and Caicos Islands
Providenciales is the center of Turks and Caicos, but it’s the surrounding islands that make this a world-class island-hopping destination. Grand Turk brings history and a small-town charm that feels far away from the resorts of Provo. Salt Cay is tiny, remote and remarkably peaceful, with beaches that often sit empty. Then there’s North Caicos, Middle Caicos and South Caicos.
There are also dozens of uninhabited cays — little strips of sand and rock that appear on the horizon and disappear again — each offering its own version of turquoise perfection. With regular ferries and easy charter options, it’s simple to build a trip that hops between islands without ever feeling rushed.
Trinidad and the Gulf of Paria
Just off Trinidad’s western coast, the Gulf of Paria hides a small archipelago of quiet green islands. Chacachacare, Monos and Gaspar Grande are the best known — lush, low-lying and perfect for short day trips. They feel a world away from Port of Spain, even though they’re only a quick boat ride from the mainland (we recommend hiring a professional tour guide).
These islands carry a different kind of island-hopping energy — less polished, more adventurous. They’re places where you can picnic under the trees, swim in calm water and spend a day with nothing but the sea around you. It’s a side of Trinidad that even many travelers don’t know exists, with names like Centipede Island.
Of course, there’s Tobago, too! With an easy shuttle on Caribbean Airlines.
Cayman Islands
The Cayman Islands are a trio of distinct destinations tied together by small planes and ferry routes. Grand Cayman is lively and beach-forward, home to Seven Mile Beach and the islands’ major resorts. Cayman Brac is more rugged, with limestone bluffs, caves and quiet coves. Little Cayman is tiny, tranquil and wrapped in one of the best reef systems in the Caribbean.
Hopping between them gives travelers a layered experience — big island energy, island-time quiet and true remoteness, all within a short flight. It’s an itinerary that’s both simple and deeply rewarding.
Antigua and Barbuda
Antigua is the hub, with its historic harbors and famously plentiful beaches. Barbuda lies just north, an easy ferry or flight away. There, pink sands stretch seemingly forever, and the landscape feels untouched. It’s easy to extend the journey — Montserrat, St Kitts and Nevis are all within reach.
Each of these neighboring islands has its own strong sense of place. Montserrat is volcanic and green, St Kitts is relaxed and deeply historic, and Nevis carries a timeless charm. It’s an island-hopping route that layers old Caribbean character with natural beauty and ease of movement.
Karen Udler
2025-10-21 01:41:00