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Which Caribbean sailing destination is right for you?

With charter bases from the top of the Bahamas to the bottom of the Caribbean, Dream Yacht Charter is well-positioned to help you find your ideal island.

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Dream Yacht Charter- The World’s Leading Ocean Tourism Company Dream Yacht Charter

Let’s face it—it’s pretty hard not to have an amazing time sailing in the Bahamas and Caribbean. The islands paint the classic picture of paradise itself with their powdery soft beaches, sublimely swimmable water and cocktail-worthy sunsets. Yet each island group offers a distinct experience, catering to different interests and sailing skill levels. So, where do you start?

Dream Yacht Charter has more than 10 bases spanning this region. The charter company is one of the largest in the world, with 45-plus destinations globally and a greater variety of yachts to charter than any other. “Choosing the right destination for both you and your crew is key to the overall cruising experience,” says Carol Hansen, head of marketing, Americas, for Dream Yacht Charter. Some factors to take into consideration, she says, are the distance from home, sailing difficulty, activities offered, boats available and the array of must-see spots — or, to put it in today’s terms, Instagram-worthiness.

With its broad expertise, Dream Yacht Charter gives us a rundown of the region’s most popular destinations.

Abaco, Bahamas

Best for: Bahamian conch fritters and short passages

Don’t miss: the Sunday afternoon party at Nipper’s on Great Guana Cay

Settled by Loyalists fleeing the colonies in the 18th century, the Abaco Islands are peppered with fascinating colonial settlements and have some of the friendliest locals you’ll find anywhere. This northern Bahamian enclave consists of the main island of Great Abaco and a string of barrier cays; in between is the ultra-calm Sea of Abaco, which makes island-hopping a breeze. The lagoon is fringed with well-protected anchorages and mooring fields that give access to restaurants, bars and golf. An easy destination to get to, the main hub of Marsh Harbour, where Dream Yacht Charter’s base is found, is less than an hour by plane from South Florida.

Exuma yacht charter- The perfect tropical destination Dream Yacht Charter

Exumas, Bahamas

Best for: pristine natural beauty and solitude

Don’t miss: hiking to Blackbeard’s lair on Warderick Wells

The waters of the Exumas simply don’t look real. They’re too blue, too clear, more like a swimming pool than the sea. Amid these idyllic waters, swirling white sands create art in the current. This is Mother Nature at her best, rivaling the most scenic anchorages of the South Pacific. Add in sociable swimming pigs, rare iguanas and guaranteed shark sightings, and nature lovers and social media mavens will be in heaven.

The leeward side of the island chain produces smooth waters, and those who love to helm will appreciate the long passages here. There is literally an island for every day of the year, so boats can spread out and solitude can be found.

US Virgin Islands

Best for: the mix of nature and luxury

Don’t miss: picking up a New York-style pizza by paddleboard from the floating Pizza Pi

There is no easier destination than the USVI for US citizens—no passport required! Just fly in to St. Thomas and head to Compass Point Marina, where Dream Yacht Charter’s fleet of monohulls and sailing cats awaits.

St. Thomas has been a duty-free port for nearly 300 years, and jewelry shops are a specialty. Contrasting the bustle there, St. John is mostly covered by the Virgin Islands National Park, crisscrossed with hiking paths above the waterline and flush with great snorkeling sites below. Between these main islands, the recently opened Lovango private island resort brings a new level of luxury to these parts and offers visiting yachts day passes for its five-star beach club.

British Virgin Islands

Best for: easy sailing and beach bars

Don’t miss: a Painkiller cocktail at the Soggy Dollar bar on Jost van Dyke

There’s a good reason why the BVI is one of the world’s most popular sailing destinations. Between the verdant hills and white-sand beaches, the Sir Francis Drake Channel provides consistently great sailing conditions on flat waters, and passages are generally line of sight.  Its watering holes are legendary, running the gamut from elegant barefoot beach clubs to the more boisterous Willy T pirate ship. Foxy’s, for instance, is one of the top five places in the world to ring in the New Year. Dream Yacht Charter has a huge fleet of 84 yachts at its Scrub Island base to meet the demand. With COVID restrictions finally lifted, now is a great time for first-timers to get their feet wet, so to speak.

St. Barts
Sailing to the island of St. Barts is a St. Martin yacht charter favorite. Dream Yacht Charter

St. Martin

Best for: variety—a mix of cultures, action and nature

Don’t miss: a cheeseburger in paradise at the bar that inspired the song, St. Barts’ Le Select

A major superyacht hub, St. Martin is the takeoff point to visit the secluded coves of quiet Anguilla and the St. Tropez-esque shops and restaurants of chic St. Barts. It’s also a destination unto itself. Called St. Maarten and St. Martin, the island has a dual personality with half an overseas region of France and half belonging to the Kingdom of the Netherlands. Dream Yacht Charter’s base, offering a good mix of monohulls and catamarans, can be found on the French side. Highlights include traipsing around uninhabited Tintamarre, a nature reserve island off the northeast coast, and dining on French and Creole cuisine in Grand-Case.


Best for: endless beaches and excellent sailing

Don’t miss: snorkeling beneath the limestone Pillars of Hercules

Antigua’s jagged coastline gives sailors a spoil of choices when it comes to finding safe harbors. You can also make landfall on a new beach every day and not repeat any for an entire year. As the host for several international sailing events, the island is consistently caressed with gentle trade winds, making for ideal sailing conditions. It’s been a magnet for mariners since the late 1700s when the British navy set up base at Nelson’s Dockyard, now a UNESCO World Heritage Site and definitely worth a visit. Part of the military base was the Shirley Heights lookout, which is now the place to be for a Sunday evening sunset.


Best for: the laid-back French Caribbean vibe

Don’t miss: rum tasting at Depaz, a distillery operating since 1651

Uncrowded beaches, quaint seaside towns and an interior of rainforest-covered volcanos—what’s not to like? Provisioning in Le Marin, where Dream Yacht Charter is based, will have charterers eating like King Louis on board with good prices on French wine, cheeses and charcuterie. The cruising ground is easy to navigate and relatively compact, so if you choose to stay in Martinique, you can explore the calmer leeward side at a relaxed pace or circumnavigate the island on a weeklong charter. It’s also a jumping-off point for exploring farther south to St. Lucia, St. Vincent or even a charter to Grenada.

Tobago Cays
Grenada and Tobago Cays Dream Yacht Charter


Best for: adventure and lively sailing

Don’t miss: snorkeling or diving the Molinere Bay Underwater Sculpture Park

A great summer sailing option south of the Hurricane Belt, Grenada is best appreciated by sailors who are comfortable with lively bluewater sailing. It’s a gateway to the gorgeous Grenadines, or the endpoint for one-way charter south from Martinique. The island itself is fragrant with tropical rainforests and spice plantations producing cinnamon, cloves, ginger, mace, allspice and nutmeg. Hikers can chase waterfalls here, rewarding themselves with a swim beneath the cascade, and advanced divers can discover the “Titanic of the Caribbean.”

sailing the caribbean
Choose the perfect charter destination with Dream Yacht Charter Dream Yacht Charter

Above all, when choosing a destination, remember to keep it fun. “If you plan to skipper the boat, make sure you’re comfortable with the skill level required or choose to hire a skipper,” Hansen advises. “Getting familiar with the cruising ground with a little research in advance also helps a great deal, so you’ll feel more confident when you arrive for your amazing week on the water.”

Find sample itineraries and browse available yachts at https://dreamyachtcharter.com.

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