For those seeking a truly private Caribbean experience, there are few better options than a yacht charter. A luxurious yacht not only offers an exclusive space for multi-generational family gatherings or a special trip with a groups of friends, but the ultimate choose-your-own-adventure on the balmy seas. Pre-Covid, an itinerary may have included ventures to multiple countries and island groups, most sailings now take a simpler approach to avoid the varying entry requirements across administrative areas. The benefit? You get to spend more time exploring all that a destination has to offer, traversing between marinas, islets and coves with the luxury of a boat all to yourself. This change also means that crews have upgraded their onboard and water-based activities, often adding amenities like eFoil boards and new waterslides, plus scavenger hunts and watersports competitions between passengers and crew. Read on for the best destinations for yacht charters in the Caribbean.
Related: The Benefits of Going Private
Contact Indagare or your Trip Designer to discuss whether flying, sailing or staying private is right for you or to learn more about Covid travel safety, including the destinations that are open to travel, new Covid hotel policies, future trip-planning advice, inspiration and ideas.
For Maximum Boat Time: Antigua and Barbuda
A week-long charter in Antigua and Barbuda is ideal for a slow-paced sailing, with an emphasis on yacht-time at beautiful anchorages. Antigua’s Nonsuch Bay, English Harbour, Morris Bay and Jolly Harbour are protected harbors where a boat could stay for several days, surrounded by gentle green slopes, while passengers enjoy the area’s diving and snorkeling. And over in sparsely uninhabited Barbuda, yachters can enjoy the low-lying island’s near-empty (and gorgeous) beaches. For more onshore activities, excursions could include horseback riding, rum-making and zip-lining, plus Nelson’s Dockyard, a restored 18th-century marina.
For Island-Hopping: St. Vincent and the Grenadines
St. Vincent and the Grenadines, with its 32 isles and cays, makes an excellent destination for seeing multiple islands that offer a relaxed, refreshingly quiet setting (especially true since jet skis and waverunners are banned from its waters). Much of the archipelago is uninhabited parkland, making for striking views, crystal-clear seas and minimal crowding. Plus, there’s opportunity to change the scenery every day, from the white-sand beaches of Canouan—an under-the-radar getaway with a lush, hilly interior—to the exclusive shores of Mustique. There, passengers can spend days offshore before stopping by Basil’s Bar, the open-air waterside local institution frequented by the likes of Kate Moss and the Duke and Duchess of Cambridge.
For Even More Island-Hopping: The British Virgin Isles
A favorite of celebrities and billionaires, the four large islands and 50 smaller cays of the British Virgin Islands are home to both dreamy tranquil shores and a sceney nightlife. Days can be spent snorkeling and diving at secluded beaches on Anegada and blissful Peter Island, visiting the grottoes and pools of the geological wonder known as The Baths or exploring the sugar mill ruins and the natural sea-formed hot tub on Jost Van Dyke. The Dutch-named island is also home to Soggy Dollar Bar, a beach institution that created the Painkiller cocktail (rum, pineapple and orange juice and cream of coconut poured over crushed ice). Come sunset, Tortola Island is a favorite hangout for dining out and dancing well into the night.
For the Foodie & Scene-Seeker: St. Barth’s and St. Martin
This year, boats can sail freely between St. Barth’s and the French side of St. Martin. At the latter, the best place for anchoring and spending time on the water is off Grande Casse or at Île Tintamarre, an uninhabited islet with a secluded beach. Most of the trip, though, will likely be just off St. Barth’s, and for good reason. The island is a perennial favorite for Indagare members, and yachts usually anchor outside of Gustavia, by Colombier Bay or off St. Jean. Expect days (and long lunches) at Nikki Beach Club or browsing the island’s high-end boutiques and evenings at some of the Caribbean’s most buzzed-about restaurants, before returning to the boat.
For a Long, Blissful Endeavor: The Bahamas
For longer yacht charters or the opportunity to travel greater distances, consider the Bahamas, with its 2,000-plus islands situated between Florida and Cuba. A sample itinerary could sail from Nassau to Staniel Cay and back, stopping at new coves every day for beach barbecues or other on- and off-shore activities. Two favorites: Shroud Cay’s “washing machine,” where a steady current sends swimmers and snorkelers through a narrow channel, and Thunderball Grotto, a swimmable, underwater cave system rich with marine life (named for the eponymous 1965 James Bond film which was shot here).
For an Accessible Getaway that Feels Far-Flung: St. Lucia
The Caribbean’s most dramatic scenery is in St. Lucia, where the volcanic spires known as the Pitons rise more than 2,500 feet from the sea. The geological wonders are a UNESCO World Heritage site, and the best way to view them is from the water. Hiking the island’s dense rainforest is a must, but so is taking the time to explore St. Lucia’s vibrant arts culture, rich history (with African, Indian and Creole influences) and world-class diving opportunities. Entry requirements-permitting, St. Lucia is also easily incorporated into a trip around the Grenadines.
For a (Gorgeous) Domestic Getaway: U.S. Virgin Islands
The U.S. Virgin Islands let visitors experience the ultimate Caribbean setting without leaving the country. Here, it’s easy to spend an entire week on a yacht exploring St. Thomas and St. John—most of which is a national park, which protects both its mountainous, tropical terrain and coral-strewn waters. Crews anchor in a different bay every day, stopping at ultra-scenic harbors such as Magens Bay in St. Thomas and St. John’s Trunk and Francis bays.
Contact Indagare or your Trip Designer to discuss whether flying, sailing or staying private is right for you, or to learn more about Covid travel safety, including the destinations that are open to travel, new Covid hotel policies, future trip-planning advice, inspiration and ideas.