Every question to ask before booking a Caribbean cruise

It’s easy to see why the Caribbean has long been the world’s favourite cruise destination - 4cornersimages/Gafanter Grafaenhain

The Caribbean has long been the world’s favourite cruise destination, and it’s easy to see why. With its natural bounty of sparkling cobalt seas dotted with tiny exotic isles hugged by gentle trade winds and a year-round temperate climate, the region was made for cruising.

So it’s not surprising that nearly all the world’s cruise lines ply these waters, with larger ships sticking to the more developed islands, and smaller vessels seeking out tiny hideaways. But with so much choice on offer, booking your first Caribbean sailing can feel daunting: Eastern or western? Big ship or boutique? Sun-soaked beach days or culture-rich island hopping? This guide cuts through the noise, breaking down the routes, styles and standout experiences to help you find the Caribbean cruise that suits you best.

In this guide:

• Before you book
• Who to cruise with?
• Ports and sights

Before you book

Where can I go?

While the Caribbean is concentrated along cultural and historical characteristics of English, Dutch, French and Spanish, cruise lines generally divide it along more geographic groupings of eastern, western and southern islands. The first two tend to be the most popular itineraries, especially for seven-night sailings departing from US ports, most notably Miami, or from the islands themselves.

Eastern Caribbean voyages typically call at Barbados, St Lucia, St Kitts, the Virgin Islands and Grenada, with some also including the Turks and Caicos Islands.

Western Caribbean voyages tend to concentrate on Jamaica, the Dominican Republic, Mexico and Central American ports such as Roatan, an island off the coast of Honduras, and Belize. When Cuba opened up to cruises, it also appeared in western Caribbean itineraries, but no US lines and very few others feature the country now.

Southern Caribbean itineraries usually include a mix of the above, plus Costa Rica and the Netherlands Antilles islands of Aruba, Bonaire and Curacao.

Most larger operators, such as Norwegian Cruise Line (NCL), Virgin Voyages, Disney, Royal Caribbean and MSC Cruises, even have their own private islands or retreats. They’re mainly found in the Bahamas and offer a resort-style experience with water sports and beach barbecue.

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When should I go?

The Caribbean’s balmy climate, with temperatures hovering between 20 and 30C, makes it ideal for year-round cruising. However, it’s from December to April when the islands come into their own as the promise of warm sunshine is a tempting escape from the gloom and chill of the UK winter. Conditions are also less humid during these months than in hurricane season, which runs from June to November.

Despite the threat of storms, many cruises still run during the summer as ships can change course to avoid bad weather. However, bear in mind that there could be a higher risk of disruption to itineraries during these months. It’s also worth noting that some countries in the southern Caribbean, such as Grenada, Barbados and the Dutch Antilles, have a very low hurricane risk.

Caribbean itineraries typically focus on exploring the Western or the Eastern islands, including the Virgin Islands - Alastair Miller/Viking Cruises

How long should I go for?

Though shorter sailings with a party vibe depart Florida ports for the Bahamas, one or two-week voyages are most common. Longer cruises may visit the Pacific via the Panama Canal, stopping at the likes of Puerto Limon in Costa Rica and Cartagena in Colombia.

It’s also possible to explore the Caribbean either as part of a world cruise or by just booking a sector of the sailing that features the islands.

Should I take a UK departure or a fly-cruise?

For anyone not wanting to fly, there is a smattering of transatlantic sailings from the UK, though as it takes around 10 days to reach the Caribbean, these suit those with time to spare.

When ships move to the Caribbean at the start of winter, returning the following spring, passengers can cruise one-way and fly the other as part of two-week packages. Cruises that feature transatlantic crossings both ways tend to be at least three weeks.

Fred Olsen Cruise Lines and Cunard tend to offer one-off Caribbean round-trip sailings and also feature the region as part of their world cruises, while Saga sometimes offers ex-UK Caribbean sailings.

Ambassador Cruise Line features fly-cruises to the islands, but also has a handful of round-trip Caribbean sailings from Tilbury, while Marella Cruises bases several ships in the Caribbean for fly-cruises, with departures from La Romana in the Dominican Republic and Barbados.

Among UK brands, P&O Cruises bases at least one ship, sometimes two, in the Caribbean each winter, offering one-way repositioning voyages between Southampton and Barbados and Antigua at the start and end of the season. One-off round-trip voyages to the islands are also offered.

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Who to cruise with?

Mainstream lines

The biggest names, such as Royal Caribbean, NCL, Princess, Celebrity and MSC Cruises, offer the most popular routes with most departures from the main Florida ports, though alternatives include New York or Galveston in Texas.

Carnival Cruise Line’s offerings include short cruises to the Bahamas from a range of US ports, while Virgin Voyages brings a fresh flavour to Caribbean explorations with departures from Miami and Puerto Rico.

Disney Cruise Line departs from Port Canaveral, among others, to cater for guests wanting to combine a cruise with a stay at Walt Disney World.

The bigger cruise lines, such as Royal Caribbean, typically depart for the Caribbean from Miami - MARIA ALEJANDRA CARDONA/Reuters

Luxury options

Premium lines, including Azamara, Oceania, Silversea, Regent Seven Seas Cruises and Seabourn, usually sail from Miami, but some offer departures from Caribbean ports too.

French company Ponant features the French Caribbean islands heavily with many of its voyages departing from Martinique, St Martin and Guadeloupe, while boutique line SeaDream Yacht Club, which has two mega-yachts for just 112 guests, sails to a host of Caribbean hideaways, departing from St Martin, Puerto Rico and St Thomas, among others.

Tall ship lines Star Clippers and Sea Cloud Cruises offer similar off-the-beaten-track itineraries with departures from St Maarten and Barbados, as does Windstar Cruises.

The luxury mega-yachts of the Ritz-Carlton Yacht Collection are newcomers to the Caribbean - Edgardo Contreras

Alternatives and newcomers

Newcomers to the Caribbean scene are the mega-yachts of the Ritz-Carlton Yacht Collection, representing the upscale hotel chain’s first foray into the cruise world, and Emerald Cruises, better known for its river cruises, but more recently branching into ocean and coastal voyages. Sister line Scenic also ventures to the Caribbean for cruises on its upscale “Discovery Yacht” Scenic Eclipse.

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Ports and sights

Which itinerary should I follow?

The smaller the ship, the more off-grid you can go, by sailing into pocket-sized ports in some of the larger destinations or visiting tiny hideaways, mooring up in beautiful bays and going ashore by tender (small boat).

Such is the Caribbean’s versatility, passengers can enjoy a completely different experience away from the shopping centres and duty-free stores of the more commercialised ports, to tiny rum shacks on deserted beaches and sleepy villages tucked into lush, jungle-covered hills.

These sailings depart from one of the main islands, such as Barbados, making it easy for guests flying in from Europe or the US, before charting a course that takes them well away from the mass-market ships.

In the Grenadines, the unspoilt isles of Mayreau, Union Island and Bequia can be discovered by smaller ships, along with the Tobago Cays – where visitors can swim with wild turtles in the sparkling aquamarine waters.

Bequia Island in the Grenadines can be reached by smaller boats

In the British Virgin Islands, alternatives to the main island of Tortola include Jost Van Dyke, Virgin Gorda and Norman Island.

In the French Caribbean, celebrity hotspot St Barts, Guadeloupe and Iles des Saintes welcome the select crowds smaller ships bring.

St Kitts can cater for the world’s largest ships, but its smaller sister, Nevis, with rain-forested hills dotted with old sugar plantations, is for smaller craft.

On St Lucia, Vieux Fort is a quieter alternative to Castries; on Dominica, boutique ships swap busy Roseau for a smaller port close to the town of Portsmouth; Marigot, the main town of French St Martin, is a far cry from Philipsburg, the commercialised capital of Dutch St Maarten.

The Dominican Republic is a popular stop on a Caribbean cruise - Nico De Pasquale Photography/Getty Images

Where can I depart from?

The most popular US departure ports for Caribbean cruises are in Florida, with Miami, Fort Lauderdale, Port Canaveral and Tampa leading the way; alternatives include New York, New Orleans, Galveston in Texas, and Charleston in South Carolina.

It is also possible to fly to a Caribbean island and cruise from there, with departures offered from points including Barbados, Antigua, Puerto Rico, Martinique, St Lucia and St Maarten.

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About our expert

Sara Macefield

After finding her sea legs 20 years ago, Sara has gone on an estimated 200 voyages (and counting) across the world’s oceans and rivers, with Antarctica and the Galapagos Islands scoring as all-time favourites.

Telegraph Travel’s cruise expert, Sara Macefield

This article was first published in March 2023 and has been revised and updated.

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