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Travel bucket list idea:

Cruise the Caribbean

  • Multiple countries

  • Bucket List Experience

Last updated: 19 March, 2024

The Caribbean is the world’s most popular cruise destination, and little wonder. Vibrant cultures, music, gorgeous beaches, watersports galore and tropical sunshine are the ingredients for a dream cruise for many. Because there’s so much to do, the Caribbean suits anyone; families, honeymooners and groups of friends.

You’ll need to choose either a big ship or a small ship – both offer a slightly take.

Big ship cruising

The main advantage of big ships is that it’s essentially a floating resort, packed with bars and restaurants, complimentary kids’ clubs, evening entertainment and daytime activities. Days at sea between ports can be as lively or as laid-back as you like.

Several of the islands are well equipped to handle big ships, among them Barbados, Antigua, St Maarten, the US Virgin Islands, New Providence in the Bahamas, St Kitts and Jamaica. In each, you’ll find a vast range of activities, from snorkelling and kayaking to hiking, horse riding and visits to plantation houses, rum distilleries and historical forts.

The big cruise lines have their own private islands or beaches, too; Royal Caribbean’s Perfect Day at CocoCay is a luxurious resort offering everything from zip-lining to overwater cabanas. Disney Cruise Line, MSC, NCL, Virgin and Carnival Cruise Line also have private islands offering the experience of a day in a luxurious resort.

Small ship cruising

Smaller ships offer many advantages over their bigger counterparts.

They can visit Caribbean islands beyond the reach of bigger vessels. They can stop in secluded anchorages or fit into harbours that are off limits to their larger sisters.

You might thread your way through the Grenadines, visiting tiny Bequia and the gorgeous Tobago Cays, for example, or explore hideaways in the British Virgin Islands such as Jost Van Dyke and Virgin Gorda. Small ships can call at swish St Barths, or sleepy Anguilla and even the volcanic island of Montserrat.

These are places big ships generally can’t offer, so you won’t have a sense of being lost in a crowd. There’s also the sense of a more authentic experience on smaller, quieter islands.

Small ships don’t overwhelm tiny ports, either. There’s flexibility in the itinerary, should you need to change course for any reason. Best of all, some small ships have swim platforms at the back so you can dive straight into the blue Caribbean on swimming stops.

Other options

Expedition ships occasionally pass through the Caribbean, too, as they’re positioning between Antarctica and the Arctic, offering one-way voyages between smaller ports and often delving deep into the history, culture and nature of the region rather than focusing only on beaches.

Culturally-orientated lines visit the islands, too; Noble Caledonia, known for its high-brow cruises, has several itineraries visiting off-the-beaten-track islands.

You could also opt for a fully-rigged, tall ship, or ‘clipper’. These authentic ships, modelled on the original ‘greyhounds of the sea’ from the early 20th century, fly over the water with no sound but the waves, wind and creak of the lines. There are few seagoing experiences as romantic as this.


Price from: £Varies
Minimum age: Any
Age suitable: 4+
When: All year around
Duration: 5-14 days

Getting there & doing it

Caribbean itineraries range from just a few days, which would typically include, say, the Bahamas, or Key West and Cozumel. A week is better, which would normally take you to five or six ports. If you cruise from a US port, you’ll usually spend one night ashore before embarking your ship, to fit in with flight arrival times.

The big ship Caribbean cruises depart from various ports in the US, Miami and Fort Lauderdale being the two biggest hubs. There are also fly-cruises from Barbados, St Lucia and St Maarten, which means you start your journey in the islands, rather than spending a day at sea to get there. Long cruises from the UK also operate in winter.

Smaller operators tend to cover shorter distances and as such, start their itineraries in the Caribbean, rather than sailing from Miami. You’ll start in, say, Barbados, or St Maarten, or San Juan.

When to do it

The most popular time to cruise the Caribbean is between December and April, coinciding with dry, sunny weather and calm seas. Ships do, however, operate all year round.

The June to December period is more prone to hurricanes but ships can divert to avoid these.

Who to go with: tour operators


Our writer’s recommended tour operators to book with

Noble Caledonia [Caribbean]

  • Multiple countries

This culturally-focused line offers small ship cruises focusing on history and nature in off-the-beaten-track spots. A couple of itineraries include a rare opportunity to sail the coast of Cuba.

Royal Caribbean

  • Multiple countries

Royal Caribbean


Royal Caribbean

One of the world’s largest cruise lines, with a fleet of 24 ships, including four of the largest in the world. These fabulous floating resorts, that transport you between the Caribbean islands, are packed with entertainment, bars, restaurants and award-winning kid’s clubs.

Seabourn [Caribbean]

  • Multiple countries

Seabourn’s luxurious, all-inclusive ships are perfect for Caribbean cruising, with masses of deck space, al fresco dining if you want it, creative itineraries and intuitive, personal service.

Star Clippers [Caribbean]

  • Multiple countries

Star Clippers has three graceful, square-rigged sailing ships, two of which sail out of St Maarten and Barbados all winter, visiting smaller ports and offering an informal lifestyle on board.

Tradewind Voyages [Caribbean]

  • Hadleigh, Suffolk, Multiple countries

The elegant Golden Horizon sails northern Europe, the Mediterranean, Asia, the Indian Ocean and Australia, carried by the wind and currents. More eclectic and adventurous itineraries than Star Clipper.

Virgin Voyages

  • Multiple countries

Virgin Voyages


Virgin Voyages

Virgin’s snazzy, adults-only ships are aimed at a younger audience, with nightlife that would rival anything ashore and a day in the Bahamas at the cool Virgin Voyages Beach Club, on Bimini