This winter’s 10 greatest Caribbean cruises – and which one is right for you

Nine million people can’t be wrong. If you are looking for family fun, tropical adventures or a romantic break, there’s a voyage for you

The Caribbean is an alluring prospect at any time of year, but amid the dismal gloom of a British winter, its intoxicating mix of shimmering azure waters sprinkled with tropical isles becomes ever more irresistible.
With sailings from easy-to-reach Florida ports and popular islands including Barbados and Antigua, there is a vast choice of ships and sailings from virtually every cruise line – a whopping nine million passengers cruise the region annually.
Leading the pack is the world’s largest ship, Icon of the Seas – in the headlines recently after mechanical problems forced the cancellation of a planned sailing – along with a host of small, intimate craft and everything else in-between.
The Caribbean is also an ideal launchpad for new vessels with many making their debut here and this winter’s line-up of newcomers ranges from Sun Princess, Princess Cruises’ newest and largest ship, to Ilma, the latest exclusive mega-yacht of The Ritz-Carlton Yacht Collection and Explora II, the recent opulent addition to the Explora Journeys fleet.
Proving that it takes a lot to put this region in the shade, here are some of this winter’s best Caribbean cruises. To learn more, including how to plan your trip with our about Caribbean cruise guide.
Skip ahead to your ideal trip:
For thrills, spills and tons of bragging rights, look no further than Icon of the Seas, which holds the crown as the world’s largest cruise ship. This latest leviathan from Royal Caribbean International (RCI) is packed from bow to stern with family fun and up to 7,600 passengers. Kids can plunge down six slides in the largest waterpark at sea, while parents can sup cocktails at Swim & Tonic, the line’s first swim-up bar, or float around the suspended infinity pool – one of the ship’s many wow factors. 
If you can tear yourself away, RCI’s private island, Perfect Day at CocoCay, is all chill and thrill with beautiful beaches and 13 scream-inducing waterslides, including the tallest in North America.
How to do it: RCI (0344 493 4005; royalcaribbean.com) offers a round-trip seven-night Western Caribbean & Perfect Day sailing from Miami, calling at Costa Maya and Cozumel in Mexico and its private island Perfect Day at CocoCay in the Bahamas. From £1,274pp; departs April 26, 2025.
If you’re one for soaking up panoramic vistas, then Silversea’s newest ship Silver Ray is for you. The ground-breaking asymmetrical design means the ship’s main pool is on one side of the deck rather than in the middle, promising sunbathers clear views of passing Caribbean islands. Silver Ray is powered by liquefied natural gas (LNG) and advanced hybrid technology which cuts harmful emissions while in port. 
This sailing weaves through the Caribbean’s lesser-known outposts amid the rum shacks and deserted sands of pretty Bequia in the Grenadines and the dramatic vistas of St Lucia where waterfalls add a thundering soundtrack to the distinctive snaggle-toothed twin Pitons that dominate the skyline. The cobbled streets and decorative facades of Old San Juan in Puerto Rico are infused with centuries of Spanish colonial heritage that injects a lively Latino frisson.
How to do it: Silversea (0844 251 0837; silversea.com) offers a nine-night sailing from Barbados to Fort Lauderdale. From £5,700pp all-inclusive; departs March 23, 2025.
With swish designer-dripping interiors by Kelly Hoppen (formerly of Dragon’s Den fame) and others, a tastebud-tempting line-up of chic restaurants, and an ultra-swanky suite complex, Celebrity Ascent packs a cool punch. This is Celebrity Cruises’ latest ship in its revolutionary Edge-class with sleek interiors, avant-garde artworks and a novel Magic Carpet platform cantilevered off the side of the ship that doubles as a bar and restaurant, serving drop-dead gorgeous views.
Arrive in style at St Johns, the bustling capital of Antigua, an island with so many beaches it claims to have one for every day of the year, and discover the ‘white gold’ history of St Kitts aboard its atmospheric ‘sugar train’ that follows the original railroad across the former plantations.
How to do it: Celebrity Cruises (0344 493 2043; celebritycruises.co.uk) offers an 11-night Best of Southern Caribbean round-trip sailing from Fort Lauderdale. From £1,166pp; departs January 12, 2026.
A new name carving its way through Caribbean waters is Explora Journeys – an upmarket off-shoot of Italian-style cruising giant MSC Cruises – with its two ships Explora I and Explora II. The so-called lifestyle brand is promising a new era of ocean travel on its two plush all-suite ships that have won plaudits for their sophisticated spaces and luxurious auras designed to woo the well-styled and well-heeled. 
This sailing combines the Gallic chic of French island Martinique with the castaway feel of tiny Bequia in the Grenadines and the sister islands of Trinidad and Tobago that boast a sultry combination of cultures along with the evocative echoes of steel drum bands. The Caribbean’s so-called Emerald Isle of Montserrat is famed for its Irish heritage and the volatile Soufriere Hills volcano whose destructive eruptions have turned former capital Plymouth into the “Pompeii of the Caribbean”.
How to do it: Explora Journeys (0800 031 8935; explorajourneys.com) offers an eight-night Caribbean Islands from Clouds to Emeralds voyage from Barbados to Miami. From £2,850pp all-inclusive; departs December 14, 2025.
One of the must-do experiences of cruising is to sail along the Panama Canal – the famous 50-mile short-cut that links the Pacific and Atlantic oceans, saving ships from an 8,000-mile 21-day detour around Cape Horn. Princess Cruises offers sailings in both directions between Florida and California and it also offers partial transits, where ships enter the canal into the first locks before turning around and retracing their steps. On this Panama Canal east coast to west coast crossing, the colonial mastery of the Colombian city of Cartagena awaits with its Spanish balconied buildings lining a maze of narrow streets and classical squares, while Costa Rica turns on the natural charm with a diverse collection of tropical flora and fauna.
How to do it: Princess Cruises (0344 338 8670; princess.com) offers a 16-night Ocean to Ocean voyage from Fort Lauderdale to Los Angeles. From £1,456pp; departs January 24, 2026.
Dip into the spirit of Central America amid the sparkling surroundings of 746-guest Seven Seas Grandeur, the most-recent opulent addition to the Regent Seven Seas Cruises (RSSC) fleet, boasting luxury touches at every turn. Even the ship’s multi-million dollar art collection is enough to prompt open jaws at the sight of an original Pablo Picasso and bejewelled Faberge egg as the centrepiece of the lavish atrium. 
Discover a fascinating world of ancient Mayan ruins on Mexico’s Costa Maya and race through the tropical rainforest on an all-terrain vehicle at Roatan in Honduras. At the line’s private island Harvest Caye, off the coast of Belize, delve into mangrove swamps or retreat to the beaches to snorkel the coral reef and take off on a water toy in the lagoon.
How to do it: RSSC (023 8082 1390; rssc.com) offers a seven-night Fall for Caribbean round-trip Miami voyage. From £3,099pp all-inclusive; departs November 22, 2026.
Get your motor running and whizz off around the Caribbean courtesy of an exciting go-kart track that weaves across the top deck of Norwegian Cruise Line’s Norwegian Viva. When it comes to adrenaline-fuelled fun, Viva boasts some of the fastest dry slides at sea and a tidal wave waterslide, along with a host of dining spots including an upscale food market and multi-million dollar sculpture garden. 
The action continues ashore as you fly through Antigua’s rainforest on an exhilarating canopy tour or speed across the waves at the helm of an America’s Cup yacht in a dramatic race in St Maarten. Alternatively, sit back and take it easy in a volcanic mud bath in St Lucia’s famous sulphur springs – just beware the pungent pong.
How to do it: NCL (0333 241 2319; ncl.com) offers a one-week round-trip sailing from Puerto Rico. From £1,699pp; departs March 23, 2025.
Take a leisurely route to the Caribbean on this month-long sojourn with P&O Cruises that also throws in a host of US ports for good measure. Bermuda’s pink beaches and perfect golfing greens break up the transatlantic crossing, before arriving at Freeport in the Bahamas where striking out beyond the city limits exposes the peaceful soul of Grand Bahama Island with mysterious caves and deserted beaches. 
Roatan serves up a cultural mix of local arts and crafts with tropical flora and fauna discovered on jungle walks and snorkelling adventures, while Belize is a hotbed of Mayan ruins and natural marvels where howler monkeys and toucans brighten up rainforest treks. New Orleans brings the sultry jazz notes of the Big Easy and Miami brings a bright-lights, big-city slice of Floridian style.
How to do it: P&O Cruises (0344 338 8003; pocruises.com) offers a 35-night Caribbean and USA round-trip voyage on Ventura from Southampton. From £2,449pp; departs January 3, 2025.
Savour the flavours of the islands by staying a little longer and combining a sailing on Marella Discovery with a stay in the Spanish-infused resort of La Romana in the Dominican Republic. This cruise brings together the dramatic volcanic sweeps of the Caribbean’s Nature Isle, Dominica, where river-tubing and rainforest treks rule, contrasting with the dazzling necklace of sandy beaches encircling the island of Antigua. Browse the streets of the capital St John’s where duty-free stores jostle with stalls groaning under a rich haul of locally-made crafts. 
Discover the rugged allure of the Dominican Republic’s La Samana peninsula while speeding on zipwires through lush rainforests brimming with waterfalls and coconut groves and keep a lookout for the many humpback whales that migrate to these tropical waters.
How to do it: Marella Cruises (020 3451 2682; tui.co.uk/cruise) offers a 14-night package comprising a one-week round-trip Colours of the Caribbean cruise from La Romana and seven nights’ all-inclusive at the HM Alma de Bayahibe. From £2,130pp, including flights; departs January 6, 2026. 
SeaDream Yacht Club knows how to dial up the romance on its twin pocket-size mega-yachts taking just 112 guests on sailings to dreamy isles drenched with local character. Al fresco dinners on deck, poolside movie sessions and sleeping under the stars add to the heady ambience, while daytime diversions vary from tai chi and yoga to water toy fun from the ship’s marina where guests can speed off on WaveRunner water scooters. 
Stroll the cobbled streets of lush Nevis – steeped in the history of one of America’s founding fathers Alexander Hamilton, who hailed from here – and the vibrant corals and gin-clear waters of Anguilla. Rub shoulders with the jet-set in swanky St Barts and keep the sybaritic feeling flowing at SeaDream’s signature Champagne & Caviar Splash celebrations with its lavish beachside barbecue.
How to do it: SeaDream Yacht Club (0800 058 4818; seadream.com) offers a ten-night Best of the Secluded Caribbean voyage from Puerto Rico to Barbados. From £5,077pp, departs January 10, 2026.
Prices are cruise-only unless otherwise stated.
This article was first published in December 2023 and has been revised and updated.

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