The Caribbean is one of those rare places that lives up to the hype every time. With over 7,000 islands scattered across the turquoise waters between the Atlantic Ocean and the Caribbean Sea, there’s no shortage of places to explore. The real question is: where do you start?
For yacht charter guests, the Caribbean offers something no cruise ship can match: the freedom to move between islands at your own pace, anchor in secluded bays that most travelers never see, and wake up to a different view every morning. From white-sand beaches and lush rainforests to vibrant local culture and world-class water sports, the region delivers on every front.
Below, we’ve broken down the top Caribbean islands to visit and what makes each one worth the trip.
The Leeward Islands
St. Maarten / Saint Martin
One island, two countries, and twice the experience. The French side, Saint Martin, is known for exceptional dining; Grand Case in particular is a small village lined with acclaimed restaurants and widely regarded as one of the best places to eat in the entire Caribbean. The Dutch side, St. Maarten, offers a livelier atmosphere with duty-free shopping, water sports, and a bustling harbor. For charter guests, St. Maarten is a popular base thanks to its well-equipped marinas and direct flights from the east coast.
Anguilla
Just a short sail from St. Maarten, Anguilla has a serious reputation for luxury despite covering under 40 square miles. Known for world-class beaches, a sophisticated dining and spa scene, a Greg Norman-designed golf course, and outstanding wreck diving, it’s consistently ranked among the friendliest Caribbean islands you’ll find. Anguilla delivers the kind of memorable experiences that keep guests coming back.
St. Barts
If there is one island synonymous with superyacht culture, it’s St. Barts. The harbor at Gustavia fills with some of the world’s most spectacular yachts during peak season, and the island’s beaches are consistently ranked among the best in the Caribbean. The French influence means exceptional food, wine, and boutique shopping to go along with the natural beauty. St. Barts is a bucket list destination for a reason.
Antigua and Barbuda
Antigua claims to have 365 beaches, one for each day of the year. English Harbour and Falmouth Harbour are legendary in the yachting world, and the island hosts both Antigua Sailing Week and the Antigua Charter Yacht Show. Barbuda, the quieter sister island, offers pink-sand shores and a peaceful escape from the busier marinas.
St. Kitts and Nevis
These twin islands sit surrounded by coral reefs and steeped in colonial history. St. Kitts is home to the Brimstone Hill Fortress, a UNESCO World Heritage Site and one of the best-preserved fortresses in the Americas. Nevis is smaller and more serene: an ideal place to anchor, explore a historic plantation inn, or relax on a quiet beach with almost no other visitors around.
The Windward Islands
Dominica
Dominica is defined by its raw, volcanic landscape; thick rainforests, over 365 rivers, dramatic peaks, and some of the most extraordinary natural features in the region. The Boiling Lake is Dominica’s signature attraction: a volcanic crater lake reached by a challenging inland hike and one of the largest of its kind in the world. For nature lovers and adventure travelers, it’s unlike anywhere else in the Caribbean.
St. Lucia
Few places in the Caribbean are as visually dramatic as St. Lucia. The twin volcanic peaks known as the Pitons rise sharply from the sea, creating one of the most iconic backdrops in the entire region. It’s an ideal place to scuba dive pristine coral reefs in the morning, hike volcanic terrain in the afternoon, and enjoy a sunset dinner at a waterfront restaurant in the evening, all framed by palm trees and turquoise waters at every turn.
The Grenadines
This chain of 32 islands in the southern Caribbean is one of the most rewarding destinations for yacht charter guests. The Grenadines offer uncrowded anchorages, calm turquoise waters, and a sense of intimacy that has disappeared from many more developed islands. The Tobago Cays — a group of uninhabited islands within a protected marine park — are the highlight of any itinerary here, with exceptional snorkeling and sea turtles a common sight. For guests who want fewer tourists and no all-inclusive resort crowds, the Grenadines are among the best islands in the region.
Grenada
Known as the Spice Island, Grenada blends lush green hills, spice plantations, and warm local culture. Grand Anse Beach is one of the Caribbean’s finest stretches of sand, and the scuba diving here, including a famous underwater sculpture park, is world-class. Grenada sits at the southern end of the Windward Islands, making it a natural stopping point for charter itineraries spanning the Eastern Caribbean.
The Virgin Islands
British Virgin Islands
The British Virgin Islands are one of the premier sailing destinations in the world. With more than 60 islands and cays, protected anchorages, calm water, and short distances between stops, the BVI is about as close to a perfect charter environment as it gets. Highlights include The Baths on Virgin Gorda, the pristine white-sand beaches of Anegada, and Jost Van Dyke’s beloved Foxy’s beach bar.
U.S. Virgin Islands
The U.S. Virgin Islands offer a different kind of Caribbean experience shaped by environmental preservation, history, and extraordinary marine life. St. John is largely a national park, with coral reefs and quiet bays that feel almost untouched. St. Thomas offers dining and nightlife, while St. Croix, the largest island in the group, has crystal-clear water and Buck Island, a national monument with exceptional snorkeling.
The Cayman Islands
Grand Cayman, Cayman Brac, and Little Cayman sit in the western Caribbean and have built a reputation as one of the best island groups in the region for underwater exploration. Grand Cayman’s Seven Mile Beach is a stunning stretch of white sand and turquoise water, while Stingray City — a shallow sandbar where Southern stingrays gather in large numbers — is one of the most memorable experiences in the Caribbean. The walls, wrecks, and reefs throughout the Caymans draw scuba divers from around the globe. Little Cayman and Cayman Brac offer a quieter, more remote experience with exceptional dive sites and far fewer tourists.
The Greater Antilles
Puerto Rico
San Juan is one of the most captivating urban environments in the Caribbean. Old San Juan’s cobblestone streets, colorful colonial buildings, and historic forts give it a personality unlike any other island. The surf on the west coast is world-class, while the calmer waters to the east are ideal for scuba diving and snorkeling. With direct flights from the east coast and strong infrastructure, Puerto Rico is also one of the most convenient Caribbean starting points for charter guests.
Dominican Republic
The Dominican Republic has one of the most diverse coastlines in the Caribbean: rocky cliffs, palm-tree-lined beaches, and turquoise bays extending for hundreds of miles. The interior offers dramatic mountain scenery and lush rainforest, while the coasts deliver some of the best beaches in the region. Whether you’re after active exploration, beach relaxation, or cultural immersion, the DR covers it all.
Turks and Caicos
Grace Bay Beach on Providenciales, the main island of the Turks and Caicos, consistently ranks at the top of global best beach lists, and the water clarity here is difficult to describe without seeing it firsthand. The Caicos Bank to the south offers calm, shallow anchorage in stunning turquoise water, making it a perfect Caribbean getaway by yacht. In recent years, the Turks and Caicos has become one of the most sought-after destinations in the region, and it’s easy to see why.
When to Visit the Caribbean by Yacht
The prime Caribbean charter season runs from December through April: trade winds are steady, humidity is lower, and the region sits well outside of hurricane season (typically June through November). May and early June have also become an ideal time to charter, with good availability and fewer crowds before the summer rainy season arrives.
Plan Your Caribbean Charter with Moran Yacht & Ship
With decades in the yacht industry, Moran Yacht & Ship has deep expertise across all of these islands, not just from the broker’s desk, but from firsthand time on the water. Our team includes veteran captains and marine industry professionals who have spent years in these very destinations.
Whether you’re drawn to the sailing perfection of the British Virgin Islands, the volcanic drama of St. Lucia and Dominica, the sophistication of St. Barts, or the seclusion of the Grenadines, we’ll help you build a Caribbean itinerary that’s right for you.
Ready to get started? Contact one of our yacht charter brokers today and we’ll help you choose the right vessel and plan a Caribbean charter tailored to exactly what you’re looking for.