20 best Caribbean cruises – and which one is right for you this winter
If ever there was a destination made for cruising, it is the Caribbean. Stretching from the Gulf of Mexico to the top of South America, it is a natural treasure chest bound together by the Caribbean Sea and temperate trade winds that hug this corner of the globe in a tropical embrace.
Sprinkled like precious jewels across waters that sparkle in every shade from deep indigo to aquamarine, are thousands of islands, many of which are uninhabited. These small idylls have long caught the eyes of travellers, from the moment the explorer Christopher Columbus stumbled across them more than 500 years ago.
European conquerors who followed in his wake searching for new-world treasures laid the foundations for the English, Spanish, French and Dutch cultures that so clearly define the islands today, while the bitter legacy of slavery brought African traditions that enriched the music and customs flowing across the region.
Such vibrant cultures bring a fitting contrast to cruise itineraries that are finely balanced between bigger, more-developed islands such as Barbados and Antigua – which tend to attract resort-style ships carrying thousands of passengers – to the rustic hideaways of the Grenadines or British Virgin Islands that cater for smaller craft.
Yet the enduring appeal of the Caribbean comes down to its drop-dead gorgeous scenery, from the volcanic peaks and lush rainforest enveloping the likes of St Lucia and Dominica to the mesmerising roll-call of beaches draped around most islands like dazzling necklaces of white powder sand.
It’s no surprise that the Caribbean carries the crown as the ultimate chill-out retreat, but its rugged side also rings adventures by the score – from white-water rafting and volcano trekking to rainforest hikes, all underpinned by the captivating heritage, culture and laidback warmth of the West Indians.
While the constant balmy climate attracts passenger ships year-round, it is during the less humid months from December to April – as Europe shivers in winter – that the Caribbean comes into its own and the cruise season ramps up to its peak.
Rather like its famous rum cocktails, the sweet taste of Caribbean life packs a punch that proves hard to resist. Here is a selection of some of the finest voyages this tropical region has to offer.
Family fun
Season’s greetings, St Lucia
This festive escape to the welcoming warmth of the West Indies is a Christmas treat that promises to match anything Santa may pull out of his sack. As part of Royal Caribbean International’s first winter season of sailings from Barbados on Grandeur of the Seas, guests can board a replica Spanish galleon to sail past St Lucia’s majestic twin Pitons and kayak along mangrove-filled waterways through a Trinidad bird sanctuary, while Pirates of the Caribbean fans can hunt for locations from the film series on a tour of St Vincent.
Book it: The seven-night round-trip Southern Caribbean Island Hop from Barbados, including calls at Tobago, Grenada and Martinique, departs Dec 26. From ￡420pp (0344 493 4005; royalcaribbean.com). For more information on where to stay, read Telegraph Travel's complete guide to the best hotels in St Lucia.
Walk the plank, Bahamas
All ages can get their adrenaline fix on waterslides that twist across the deck of family-friendly ship Norwegian Escape. This 4,000-passenger plus floating fun zone is packed with bars, restaurants and a spa (for grown-up time) plus kids’ clubs and an aqua park where daredevils can walk the plank. All this before you have hit the beaches in St Thomas, taken a Jeep safari in the British Virgin Islands or snorkelled with stingrays in the Bahamas.
Book it: A one-week Great Stirrup Cay & Dominican Republic round-trip voyage from Port Canaveral departs April 2. From ￡680pp (0333 241 2319; ncl.com). For more inspiration on where to stay in the Bahamas, read our complete guide to the best hotels in the Bahamas.
Cruise to the reggae beat, Jamaica
Turn up the half-term heat on this February escape aboard MSC Cruises’ new flagship MSC Seashore, themed on New York with a mini Statue of Liberty and Times Square entertainment area. Families can splash around in the water park and six swimming pools, while youngsters can revel in the biggest child-friendly area in the MSC fleet with futuristic-themed kids’ clubs. Catch Jamaica’s reggae rhythms at Ocho Rios, climb nearby Dunn’s River Falls and explore MSC’s new Ocean Cay Marine Reserve in the Bahamas where watersports and beach chills rule the waves.
Book it: A one-week Caribbean & Antilles round-trip sailing from Miami departs Feb 12. From ￡709pp (020 3889 5487; msccruises.co.uk). For more inspiration, read Telegraph Travel's complete guide to the best hotels in Jamaica.
Sail to Disney’s private island, Nassau
Join Mickey Mouse and the gang for a stardust-sprinkled escape that combines a stay at Florida’s Walt Disney World (and family tickets to the theme park) with a mini-cruise to Nassau and Disney’s own private island resort Castaway Cay. Here, guests can join Disney characters on the manicured sands for a day of high-octane jetboat rides and adrenaline-pumping waterslides, or simply take it easy on gentle bike meanders and enjoy some beachside chilling.
Book it: A 10-night package, departing Feb 11, includes a week at Walt Disney World’s Art of Animation Resort and a three-night Bahamas cruise from Port Canaveral. From ￡2,353pp, including flights (0800 169 0730; disneyholidays.co.uk)
Time for two
Love it up, Bimini
Ramp up the romance on a Valentine’s sailing with adults-only newcomer Virgin Voyages, which proclaims to have hurled cruising conventions overboard. Sailors (as guests are nicknamed) on the debut ship Scarlet Lady can dive into drag queen brunches, be inked in the tattoo parlour and get frisky with a Time to Play in-cabin sex kit. The fun continues at VV’s Beach Club on the Bahamian isle of Bimini where lazy days of chilling and yoga give way to DJ-led sunset dance blow-outs. On Mexico’s Costa Maya, with its ancient ruins, biking tours and river tubing keeps the fun feel flowing.
Book it: A five-night round-trip sailing from Miami departs Feb 13. From ￡780pp (0800 408 6200; cruise.co.uk)
Cocktail cruisin’, Cuba
Cuba’s unique form of Caribbean-style communism makes it the star turn of this sailing on adult-only ship Marella Explorer 2, which overnights in Havana where sleek American 1950s cars purr through colourful streets from the Spanish colonial era. You can also take the plunge to swim with tame stingrays in Grand Cayman, whose spectacular corals and gin-clear waters make it one of the world’s top diving spots. Alternatively, pitch your towel and relax on gleaming alabaster sands stretching as far as the eye can see on the appropriately named Seven Mile Beach.
Book it: A one-week Flavours of the Caribbean round-trip sailing from Montego Bay, Jamaica, calling at Cozumel in Mexico, departs Jan 18. From ￡1,376pp (020 3451 2682; tui.co.uk/cruise)
Get yachting thrills, St Maarten
Ever wondered what it’s like to race an America’s Cup yacht in an exhilarating head to head? This Azamara cruise lets guests join the crew on one of the St Maarten-based racing craft to “work the boat” or sit back and enjoy the action during a high-thrills contest. Dial down the pace on a lazy snorkel trip from St Thomas aboard a champagne-stocked catamaran and track down French revolutionary history on Guadeloupe where the spirit of Napoleon lives on in a fort-turned-museum named after him.
Book it: The 12-night Caribbean Breezes round-trip voyage from Miami departs Feb 3. From ￡1,467pp, including flights (0344 493 4016; azamara.co.uk).
Adventures ahoy
In the footsteps of explorers, Cartagena
With no planes to catch, forget about airline luggage limits aboard Fred Olsen’s Borealis. Sailing from Southampton, this trip follows the well-worn route of explorers across the Atlantic. Roll to the rhythms of Caribbean island life in Antigua and St Kitts. Peel back the centuries in the beautifully preserved streets of Colombia’s walled city Cartagena, and admire the modern engineering marvel that is the Panama Canal. Sleepy sloths and colourful toucans inject animal magic by the bucketload in eco-haven Costa Rica.
Book it: A 34-night Cultural Caribbean and the Americas round-trip cruise from Southampton, calling at the Azores, Belize City and Bermuda, departs Jan 6. From ￡5,799pp (01473 742424; fredolsencruises.com). For more inspiration on where to stay, read Telegraph Travel's complete guide to the best hotels in Cartagena.
Turtle time, Grenadines
Get to know the Caribbean better on a Smithsonian Journeys voyage with the French line Ponant, tailored to English-speaking guests. Onboard lecturers bring added insight as the expedition mega-yacht Le Dumont-d’Urville showcases Unesco heritage sites including St Lucia’s distinctive twin Pitons, along with the hot springs and boiling lake of Caribbean “Nature Isle” Dominica. Snorkelling with wild turtles is a highlight of the Tobago Cays in the Grenadines, where neighbouring isles Bequia and Mayreau are the epitome of exotic escapism.
Book it: A one-week Cruising the Caribbean’s Windward Islands from St Lucia to Barbados departs Feb 13. From ￡2,920pp (0808 234 3802; uk.ponant.com). Read more: Telegraph Travel's complete guide to the best hotels in St Vincent and the Grenadines.
Go pirate, Antigua
Who can resist crying out “Ahoy me hearties” while scaling a 50ft mast to the crow’s nest on a tall ship, chasing the pirate spirits of Blackbeard and Calico Jack who dominated these waters hundreds of years ago. This voyage on magnificent five-masted full-rigger Royal Clipper relives the era of the Golden Age of Sail as it carves a course from the rainforests of Dominica to the historic Georgian columns of Nelson’s Dockyard in Antigua and the picturesque sand-fringed bays of Iles de Saintes off the coast of Guadeloupe.
Book it: A one-week Windward Islands round-trip sailing from Barbados departs March 19. From ￡1,610pp (0845 200 6145; starclippers.co.uk). Read more: A complete guide to the best hotels in Antigua and Barbuda.
Play with fire, Montserrat
Be among the first to sail on Viking Cruises’ new expedition ship Viking Octantis on its debut next year to explore the Caribbean’s tucked-away spots. Toast the Irish heritage of Montserrat with a pint of Guinness and see how eruptions from the smoking Soufriere Hills volcano have rendered much of the island off-limits, transforming the former capital Plymouth into a modern-day Pompeii. Hike to the top of St Lucia’s distinctive Pitons and paddle through glowing bioluminescent waters on a kayak adventure in Puerto Rico.
Book it: A nine-night voyage from Barbados to New York departs on April 9. From ￡4,395pp including flights (0800 458 6900; vikingcruises.co.uk).
Mountain highs, Jamaica
Rugged Port Antonio on Jamaica’s north-east coast is famed for capturing the heart of the film legend Errol Flynn, who declared it “more beautiful than any woman I have ever known”. Guests should book early to sail aboard Crystal Cruises’ new expedition ship, Crystal Endeavor. Hike into the famed Blue Mountains and cool off in waterfalls en route. Bringing a New England feel are the clapboard houses and white picket fences of Harbour Island – famous for its glorious stretches of pale-pink sand – in the Bahamas, but another undeniable highlight is cruising through the rainforest along the Panama Canal.
Book it: A nine-night sailing from West Palm Beach to Panama City departs on Sept 30. From ￡6,440pp (0207 399 7601; crystalcruises.co.uk)
Savour the flavour
Seafood delights, Nassau
Al fresco dining takes on a new meaning aboard Celebrity Apex where sultry Caribbean evenings and far-reaching views are guaranteed from its “Magic Carpet” cantilevered platform on the side of the ship. For a slice of novel humour Le Petit Chef wins hands down with miniature cartoon chefs whose antics liven up each course as you sail towards the Dominican Republic where jungle hikes and kayak trips work up appetites. Nassau brings Bahamian cuisine of cracked conch and snapper, along with superb snorkelling and bargains at its famous Straw Market.
Book it: A one-week Eastern Caribbean and Bahamas round-trip voyage from Fort Lauderdale departs Jan 12. From ￡734pp (0800 441 4055; celebritycruises.com). Read more: Telegraph Travel's complete guide to the best hotels in Nassau.
A taste of Gallic, St Barts
Nicknamed the “foodies’ cruise line” Oceania Cruises serves up mouth-watering Caribbean sojourns on the 1,250-passenger Riviera where the upscale dining in speciality restaurants is complemented by a cookery school. This voyage combines Gallic infusions of French islands St Barts and Martinique, where hiking and rib boat adventures rub shoulders with rum distillery visits. Puerto Rico’s Latin flavours are captured on culinary walking tours of the capital, San Juan, while Antigua makes a splash with champagne and lobster catamaran cruises.
Book it: The 10-night Atlantic & Amber Gems round-trip voyage from Miami, also including St Lucia and private island Great Stirrup Cay in the Bahamas, departs Dec 3. From ￡2,469pp (0345 505 1920; oceaniacruises.com)
Shaken and stirred, San Juan
Handcraft your own cocktail at a San Juan bar and learn to stir and shake the Puerto Rican way on a culinary exploration of the capital’s Old Town, or dip into the history of the island’s famous rum on a Casa Bacardi distillery tour. This Holland America Line itinerary packs in activities as diverse as underwater helmet treks in St Thomas and bobsleigh rides in Jamaica, while sailing aboard the new ship Rotterdam whose European roots are reflected in a French seafood brasserie, Italian dining spot and Grand Dutch Café which serves speciality coffees and European beer.
Book it: A 14-night Eastern/Western Caribbean sailing, including Turks & Caicos, Grand Cayman and Key West, departs Jan 2. From ￡1,739pp (0844 338 8600; hollandamerica.com)
Rum times, Tortola
The transatlantic crossings on Saga Cruises’ 35-night West Indies voyage allow ample time to sample Spirit of Adventure’s five dining venues, led by the first Nepalese restaurant at sea, an Italian trattoria and cabaret-style supper club. Wash this down with the local rum of the British Virgin Islands at a distillery visit in Tortola, rattle across the lush landscape of St Kitts in an old sugar plantation train and trundle underground in Barbados on a tram tour of the dramatic limestone caverns of Harrison’s Cave.
Book it: The Caribbean Spring round-trip cruise from Southampton, including St Lucia, Martinique and Anguilla, departs Feb 22. From ￡8,019pp (0800 300 666; travel.saga.co.uk/cruises)
Luxury lovers
Caribbean caviar, Grenadines
When it comes to decadent treats, Seabourn’s exquisite Caviar in the Surf is the ultimate indulgence. Guests don swimwear to gather in the crystal-clear shallows on the Grenadine island of Mayreau where shorts-clad waiters wade past assiduously dispensing champagne and caviar canapés at an aquatic cocktail party. St Kitts shakes things up with an exhilarating quad-bike adventure across sugarcane fields and a five-line zipwire propels daredevils over the rainforest. While in Dominica, discover Carib Indian territory on a river-tubing ride through gushing rapids and calming pools.
Book it: A one-week Classic Yachtsman’s Caribbean from St Maarten to Barbados departs Feb 26. From ￡3,799pp (0344 338 8615; seabourn.com)
Living it up, Belize
Treat yourself to a millionaire lifestyle on Seven Seas Explorer, billed as the world’s most lavish ship when it launched in 2016 with a multimillion- pound art collection featuring works by Chagall and Picasso. Grand staircases, crystal chandeliers, Murano glass sculptures and acres of marble bring extravagance to the fore as you cruise along the Central American coastline towards Guatemala. Haute-cuisine dining and personal service add extra touches.
Book it: A 10-night Basking in the Beauty of Belize round-trip voyage from Miami, including Cozumel and Costa Maya in Mexico and Roatan in Honduras, departs March 3. From ￡4,799pp including flights (023 8068 2280; rssc.com)
Champagne sailing, BVIs
Carve your way through the glittering aquamarine waters of the British Virgin Islands on one of SeaDream Yacht Club’s mega-yachts with champagne on tap in a hedonistic bubble shared with just over 100 other guests. It’s like being on your own private yacht where you can race off on jet skis from the water sports marina, dine on deck under the setting sun and even sleep under the stars on a plush “Balinese Dreambed” made up with duvets and pillows for a perfect’s night slumber al fresco.
Book it: A one-week voyage from St Thomas to Puerto Rico, including an overnight stop in St Barts, departs March 20. From ￡2,708pp (0800 783 1373; seadream.com). Read more: A complete guide to the best hotels in the British Virgin Islands.
Go Dutch in style, ABC Islands
Suited butlers and plush suites on Silver Spirit ensure you arrive in the Dutch Caribbean’s ABC islands (Aruba, Bonaire and Cura?ao) in suitably upscale style. Discover an old Second World War wreck on a semi-submersible tour along Aruba’s ivory beach-lined shores; take a snorkel tour to explore an underwater world that has made Bonaire one of the world’s top dive sites; and jump on an e-bike to pedal past the colourful Dutch gabled houses of Curacao’s capital Willemstad, where you will also find the oldest synagogue in the Americas.
Book it: A nine-night round-trip cruise from Barbados plus Bequia, Grenada and St Lucia, departs Feb 5. From ￡5,600pp including flights (0844 251 0837; silversea.com)
Prices are cruise-only unless otherwise stated.
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