The Caribbean is by far the world’s most popular cruise region—some 11.9 million passengers sailed in the Caribbean, Bahamas, and Bermuda in 2022, according to the Cruise Lines International Association (CLIA), compared to 3.2 million in the western and central Mediterranean, the next biggest market. Travelers board ships headed to the region year-round for sunny skies, sugary white sands, and the crystal blue sea. While it’s not exactly an under-the-radar destination, the best Caribbean cruises will bring you to multiple islands, including some lesser-frequented gems, and away from the larger cruise ship crowds.
On these cruises, you can explore the fascinating and diverse cultures and traditions throughout the Caribbean, and free your mind while hiking tropical landscapes or diving with colorful sea creatures. Small and medium-size ships get you to both known ports and off-the-beaten path places for more intimate beach and island experiences.
Jamaica is a popular stop on western Caribbean sailings.
Photo by Shutterstock
Where Caribbean cruises sail
The standard cruise routes in the Caribbean that the big ships visit, often on sailings from ports in Florida, are designed for a joyous and carefree vacation escape, at a price that many people can afford.
Eastern Caribbean cruises sail to tried-and-true islands such as the Bahamas, St. Thomas, St. Maarten, and sometimes Puerto Rico. Western Caribbean itineraries visit islands such as Grand Cayman, Jamaica, and Cozumel, or other ports in Mexico, and sometimes Belize and Honduras. Southern Caribbean cruises might venture to the Leeward Antilles for a taste of Dutch Caribbean culture, and attractions such as the otherworldly landscape of Aruba’s Arikok National Park.
Other popular places on the standard cruise map include the Dominican Republic, where you will find the oldest street in the Americas in the capital city of Santo Domingo; and Tortola, the largest of the British Virgin Islands, with access to beaches and mountain treks.
Ships that carry fewer than 1,000 people, and sometimes much less than that, have more flexibility in terms of ports, and sail on itineraries that venture to more low-key patches of paradise, such as the smaller British Virgin Islands; French Caribbean islands that include Guadeloupe, Martinique, and St. Bart’s; and south to the glorious, unspoiled Grenadines and Grenada.
Smaller ships also tend to slow down itineraries, with late nights or overnights in port, so that you can enjoy the local nightlife. The departure points for these cruises are places you may want to linger before or after your sailing, such as lively Barbados, both a culinary and rum capital.
Best Caribbean cruises
On the Explora I, there’s a dedicated kids club, ensuring that all members of the family have fun.
Courtesy of Ivan Sarfatti/Explora Journeys
Explora Journeys’ A Journey to an Arcadian Antilles Adventures
- Best for: luxury family sailing
- To book: 7-night Journey to an Arcadian Antilles Adventures, round-trip from Barbados, from $4,850 per person (with discounted rates for children)
- Islands: St. Lucia, St. Kitts, St. Bart’s (overnight), Dominica, Martinique, Grenada
Geneva-based MSC Group, which also owns European cruise line MSC Cruises, launched Explora Journeys this year in an effort to bring the casual luxury resort experience to the high seas. The new line’s recently debuted first ship, the 922-passenger Explora I (which we recently reviewed), is a posh multi-generational playground with four pools, pickleball, ample live entertainment, 18 restaurants and lounges, suites that connect to accommodate family groups and, key for those with youngsters, a supervised program for kids age 6 to 17 that’s open until midnight each day. The cushy Nautilus Club is equipped with foosball and the latest generations of video games and VR consoles, with activities such as technology tournaments, plus discussions on ocean conservation. Children’s bathrobes, slippers, and hangers match adult amenities. The luxe line has kids’ pricing too—up to 50 percent off fares.
Embrace the chill island vibes on the 26-passenger Vela, operated by Island Windjammers.
Courtesy of Island Windjammers
Island Windjammers’ 6-night Caribbean sailing
- Best for: laid-back island vibe
- To book: 6-night sailing on the 26-passenger Vela, from $2,825 per person
- Islands: St. Bart’s and Anguilla
Island Windjammers is the kind of under-the-radar experience you want to keep a secret. Fans love this tiny cruise line that keeps alive the long tradition of casual windjammer cruising in the Caribbean—with a 26-passenger classic clipper ship, Vela, and a 10-passenger schooner, Diamant. The company has been around since 2009 and has an amazing track record with its loyal customer base; so, if you want to book a cruise, you’d best do so well in advance. And don’t overpack; these sailings are very casual—T-shirts and shorts are the standard dress code. This experience is about lingering on islands or hanging out on deck, watching the sails catch the breeze, relaxing with a complimentary rum punch and dining alfresco. There’s also the thrilling opportunity to jump into the water from the rope swing, or to get out onto the sea on a selection of water toys, such as paddleboards and kayaks.
On the recently renovated SeaDream Yacht Club ships, passengers will truly feel the romance of traveling by sea.
Courtesy of Greg Ceo/SeaDream Yacht Club
SeaDream Yacht Club’s Saba, the Grenadines and Beyond cruise
- Best for: small ship experience
- To book: 7-night Caribbean itinerary, from $3,899 per person
- Islands: Antigua, Nevis, Saba, St. Bart’s (overnight), Guadeloupe (Îles des Saintes), Bequia and Mayreau (St. Vincent & the Grenadines), Barbados
SeaDream Yacht Club’s pair of yachts, SeaDream I and SeaDream II, cruise to dreamy Caribbean destinations in relaxed luxury. My favorite of the line’s Caribbean itineraries sails between St. John’s, Antigua, and Bridgetown, Barbados, and includes the less-visited Grenadines, though you also can’t go wrong with sailings that linger, for instance, in the British Virgin Islands. Recently renovated with a more contemporary vibe, the 112-passenger yachts deliver such luxuries as a romantic open-air overnight under a cozy duvet in a Balinese Dream Bed, isolated on the bow. There are new designer hammocks and parasols out on deck, too, as well as a pair of Jacuzzis for two. Dining is mostly alfresco, adding to the romance of being at sea.
Embrace your inner chef by enrolling in some S.A.L.T. culinary experiences on Silversea’s Silver Nova.
Courtesy of Silversea
Silversea’s Bridgetown to Fort Lauderdale, Florida cruise
- Best for: eco-conscious luxury ship
- To book: 7-night Bridgetown to Fort Lauderdale cruise, from $4,950 person
- Islands: Barbados, Bequia, St. Lucia, Dominica, Antigua, Virgin Gorda, Puerto Rico (San Juan)
On ultraluxury line Silversea’s new Silver Nova, guests linger on a reimagined resort deck with the pool not in the center, as on most cruise ships, but off to the side for optimal sea views. Relaxing on a cushy lounge chair on the Euro-centric ship (headquartered in Monaco, Silversea vessels feature contemporary Italian furnishings and a European feel onboard), you might imagine you are at a fancy resort in, say, St. Tropez. New outdoor dining and imbibing spaces add to the elevated beach club vibe. The 728-passenger ship is both the largest and most eco-friendly ship in the fleet, equipped with a large-scale hybrid power source, which combines hydrogen fuel cells, batteries, and dual engines that run on liquified natural gas. For foodies, the S.A.L.T. program focuses on local food and drink culture, both on and off the ship. In Bequia, you might splurge on a bespoke excursion about sea salt that includes a six-course lunch at Grenadine Wild Sea Salt (a company that produces artisanal sea salt from the waters off Bequia). Most excursions (though not this one) are complimentary.
This Viking sailing kicks off with an overnight in San Juan, Puerto Rico—for some extra time to explore the colorful old section
Photo by Shutterstock
Viking Cruises’ West Indies Explorer itinerary
- Best for: value
- To book: 10-night West Indies Explorer cruise, from $3,299 per person
- Islands: San Juan, Puerto Rico (overnight), Tortola, St. Kitts, St. Lucia, Barbados, Dominica, Antigua, St. Maarten, St. Thomas
For those seeking more than just a beach scene, Viking Cruises offers a broad selection of daily tours focused on cultural and natural attractions in its all-inclusive pricing. Onboard the 930-passenger Viking Sea, sailing from San Juan on a 10-night West Indies Explorer itinerary, passengers visit nine countries with the opportunity to deeply immerse themselves in the Caribbean’s British, French, Dutch, and African history. Learn about the rich tradition of batiking (an ancient cloth dying method) with a hands-on class in St. Kitts, and explore the role of women in agriculture at an organic farm in St. Lucia. The cruise starts with an overnight in San Juan, offering some time to better understand the rhythm of that city before sailing away. Among things we love about this ship is the Nordic Spa, where after a full day of active exploration you can heal your body with a warm soak then wake yourself up at the freezing snow grotto, before more warm water surrendering.
The Pink Agave restaurant on the adults-only Virgin Voyages, where it’s all about the fun drinking, dining, and social atmosphere.
Courtesy of Virgin Voyages
Virgin Voyages’ Sunsets in the Lesser Antilles
- Best for: great dining, dancing, and entertainment for grown-ups
- To book: 7-night Sunsets in the Lesser Antilles cruise, round-trip from San Juan, from $2,550 for two
- Islands: Puerto Rico, St. Kitts & Nevis, Martinique, Curaçao, and Aruba
The only cruise line on this list with vessels that accommodate more than 1,000 passengers, Virgin Voyage’s 2,770-passenger ships are restricted to adults ages 18 and up and operate with more cheekiness than formality. Adults on a Virgin Voyages’ Caribbean cruise can expect an anything goes attitude, where you can dance outdoors under the stars alongside mermaids and mermen during a themed party, when not attending beach bashes on shore. By day, work up a sweat in an ’80s-style dance aerobics class or get a tattoo or piercing from one of the visiting artists in the onboard parlor. At night, play drinking games while eating at the Korean barbecue venue or enjoy a first-rate molecular dining experience with items that pop or smoke (all meals are complimentary). Embrace the detox/retox ethos onboard with time spent in the gym and spa when not partying. Big spenders might opt for a RockStar suite, where they can entertain guests when not taking a peek-a-boo shower with wide-open views of the sea. There’s a do-good aspect, too—with sustainable products such as upcycled ocean plastic sunglasses and reef-safe sunscreen available in the shops.
Ahoy there! Windstar Cruises sailing ships make passengers feel like they are traveling back to a simpler era on the seas.
Courtesy of Jeff Zaruba/Windstar Cruises
Windstar’s Beach Fun & Sun cruise
- Best for: sailing ship experience
- To book: 7-night Beach Fun & Sun: A Remote Caribbean Getaway cruise from St. Maarten, from $3,222 per person
- Islands: In the BVI, Tortola (Soper’s Hole), Jost Van Dyke (overnight) and Virgin Gorda; Anguilla, St. Bart’s, Antigua
For an under-the-billowing-sails experience, it’s hard to top the 342-passenger Wind Surf, the largest sailing ship in the world, with sails that unfurl with the push of a computerized button (or two). You might feel like a pirate navigating the high seas on this Windstar vessel, but you can also hit the top-flight spa for an extravagant massage (indoors or open-air) and dine on excellent cuisine including fresh fish and Caribbean-influenced fare, from the official cruise line of the James Beard Foundation. There are kayaks and other water sports toys to borrow from the marina and the opportunity to walk barefoot in the sand at laid-back ports. Some of the main perks include a pampering crew and a convivial yacht club atmosphere, with live music and dancing out on deck, which are just icing on the cake.
