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The best Caribbean cruises for winter 2026 getaways
Set sail on an island-hopping adventure with these exciting itineraries from Virgin Voyages, Fred Olsen and more
From palm tree-lined beaches to crystalline tropical waters, it’s hardly surprising that an island-hopping cruise around the Caribbean is a bucket list holiday for many – and often the most-searched cruise itinerary.
A cruises offers a great way to explore the islands, with guests getting the chance to experience many idyllic destinations in one trip without being tied to one resort or region.
What’s more, several cruise lines offer guests access to private islands in the Caribbean, such as Disney’s Castaway Cay, Royal Caribbean’s Perfect Day at CocoCay and MSC’s Ocean Cay.
When it comes to itineraries, guests have the option of booking everything from transatlantic cruises, setting sail from Southampton or London Tilbury, to month-long voyages around the Caribbean. Or try a fly cruise that specifically focus on sections of the Caribbean, such as the East or West. There are even long weekend tours that set sail from Florida.
Here’s our round-up of some of the best Caribbean cruises setting sail for 2026, from adult-only holidays to family-friendly adventures.
Read more: I went on a cruise to find out if they really are just for old people
Norwegian Cruise Line: Bahamas and the Dominican Republic
Miami – Puerto Plata – St. Thomas – Tortola – Great Stirrup Cay – Miami
Departing from Miami, guests on this seven-day sailing can discover the colonial architecture of the Dominican Republic’s Puerto Plata, snorkel from the island of St Thomas and relax on Norwegian Cruise Line’s (NCL) private island Great Stirrup Cay.
This is also a chance to sail on NCL newest ship Norwegian Aqua, which features the Slidecoaster, the world’s first hybrid rollercoaster with a water slide, and an interactive digital sports complex called Glow Court. You can also relax on the ship’s Ocean Boulevard, a 360-degree outdoor promenade.
Departs 18 January 2026. From £795pp.
Read more: Why you should visit the Caribbean island you’ve never heard of
MSC Cruises: Bahamas and the Caribbean
Port Canaveral – Nassau – Ocho Rios – Ocean Cay MSC Marine Reserve – Ocean Cay Msc Marine Reserve – Port Canaveral
Calling at Nassau in the Bahamas, this four-night round-trip from Port Canaveral is a great deal to catch some much-needed sunshine this winter.
Guests will set sail on MSC Seashore, complete with the Bridge of Sighs, a breathtaking glass skywalk and its own Statue of Liberty.
The itinerary includes a stop-off at Ocean Cay MSC Marine Reserve, complete with more than two miles of white sand beaches, crystal blue waters, and plenty of activities including scuba diving, paddleboarding and beachside stargazing.
Departs 1 February 2026. From £212pp.
Read more: The best cruise deals for 2025
Virgin Voyages: Eastern Caribbean & Bimini Beach Club
Miami – San Juan – Samaná – The Beach Club at Bimini – Miami
When it comes to adults-only cruises, Virgin Voyages excels, offering onboard and off-shore entertainment in spades, from tattoo parlours at sea to days spent relaxing at the Virgin Voyages Beach Club at Bimini.
Highlights aboard this seven-night cruise aboard Resilient Lady on Scarlet Lady include the beaches of San Juan in the Dominican Republic, top golf courses in Samana and a day relaxing and partying at the cruise line’s private beach club in Bimini, Barbados.
Departs 17 January 2026; from £1,035 per cabin
Read more: All aboard the new train route exploring Mexico’s Mayan heartlands
Celebrity Cruises: Bahamas, Mexico and Cayman
Fort Lauderdale – Bimini– – Cozumel – George Town – Fort Lauderdale, Florida
Sail around the Caribbean on Celebrity Cruises’ newest ship, Xcel.
Departing from Florida, this seven-night sailing takes in the best of the Bahamas, Mexico and Cayman.
You can also enjoy the exclusive features of the new ship such as an adult-only games room and new destination-inspired entertainment space The Bazaar.
Departs 15 March 2026. From £712pp.
Read more: The best Mediterranean cruise holidays
Royal Caribbean: 3 night Caribbean cruise
Miami – Nassau – Perfect Day at CocCay – Miami
This four-night cruise is a great taster if you want to see whether a Caribbean cruise is for you.
Calling at Royal Caribbean’s private island for a Perfect Day at CocoCay experience, passengers will be able to relax among pristine sands and also enjoy giant slides in the waterpark.
You will be sailing aboard Freedom of the Seas, which has plenty of onboard activities including an ice-skating rink, rock climbing wall and surf simulator.
Departs 23 April 2026. From £274pp.
Read more: This remote Puerto Rico island is an idyllic Caribbean getaway
Disney Cruise Line: Halloween on the Seas
Port Canaveral – Cozumel – Castaway Cay – Port Canaveral
You can get in the Halloween spirit in 2026 with Disney Cruise Line.
If you’re booking a cruise for you and your family, you’ll be in safe hands with Disney Cruise Line. From Broadway-quality shows to immersive dinners and the chance for children to meet their favourite characters, Disney cruises are packed with entertainment – and this itinerary coincides with the build-up to Halloween aboard the newest ship in the fleet Disney Destiny.
Guaranteed to be filled with spooky surprises – think Disney characters in fancy dress and spooktacular desserts – this five-night Halloween on the Seas sailing will call at Cozumel in Mexico and Disney’s private island, Castaway Cay.
Departs 24 October 2026. From £3,700 per cabin.
Read more: The ultimate guide to Orlando’s best theme parks
P&O: Caribbean Discovery
Southampton – Bridgetown – Kingstown – Castries – Dominica – St Maarten – Ponta Delgada – Southampton
Visit the Caribbean without having to use an airport. This 24-night transatlantic itinerary with P&O Cruises has the convenience for UK passengers of embarking from, and returning to, Southampton.
Sailing aboard adult-only Aurora, this voyage calls at the Canary Islands en route to Caribbean hotspots such as St Maarten and Castries, promising a destination-packed tour.
Departs 3 November 2026. From £2,449pp.
Read more: Best P&O Cruises holidays
Fred Olsen: Islands of the Caribbean
Liverpool – Lisbon – Madeira – Barbados – Bequia – Grenada – St. Vincent and the Grenadines – Saint Lucia – Martinique – St Maarten – St. Kitts and Nevis – Antigua – Ponta Delgada – Liverpool
Explore nine sun-kissed Caribbean islands during this epic 32-night cruise aboard Bolette with Fred Olsen.
Departing from Liverpool, there are winter sun stops in Lisbon and Madeira en route to the Caribbean where you can try out as many of the 365 beaches on offer in Antigua, see the volcanic peaks of St Lucia and wonder through the fragrant spice markets of Grenada.
Departs 8 February 2026. From £4,899pp.
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