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Stretching from the Florida Keys to Venezuela, the 7,000 islands making up the Caribbean are scattered like jewels across the sea. With incredible beaches and sparkling turquoise waters perfect for swimming, snorkelling, and world-class diving, the balmy Caribbean is a paradise on earth.
If you long to explore this tropical paradise at a relaxed pace, why not consider travelling by sea? With guaranteed sunshine, diverse islands and, of course, rum cocktails, it’s no wonder this region is such a popular cruise destination.
If you like the sound of a Caribbean cruise, but aren’t sure which islands to visit, here are eight inspiring destinations for an unforgettable holiday.
To plan your next trip, check out our holiday itinerary helper or find holiday deals using the button below.
Note: It’s always worth checking the latest FCDO travel advice on GOV.UK before planning your trip.
1. Antigua
If you’re looking for a tropical escape, why not soak up the sun on Antigua’s white sand beaches? With over 360 stretches of sand fringing the island, the locals boast there’s a beach for every day of the year.
Cruises come into the capital of St John’s, which is home to rainbow-coloured Creole houses and the best of Antigua and Barbuda’s coastline. Here, you can visit the museum to discover the island’s history and shop for local crafts and handmade clothes.
For swimming and sunbathing, you can visit the picturesque Deep Bay beach, known for its talcum-white sand and azure seas. Or for watersports and a lively beach bar, head to Runaway Beach.
Cultural travellers can visit the 18th-century Nelson’s Dockyard in the pretty English Harbour (pictured above), where the famous admiral made his base.
And those with an adventurous spirit may like to try zip-lining in the Antigua rainforest, horse riding on the beach, or kayaking along the coast. At Great Bird Island, you can snorkel with starfish and stingrays, too.
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Fred. Olsen Cruise Lines Caribbean Christmas Island-Hopping*
Funchal - St. John's - Castries - Bequia - St George's - Bridgetown - Philipsburg - Basseterre - Santa Cruz de Tenerife
Portugal, Barbados, Grenada & 5 more | 31 nights
Departs from Southampton on the ship Borealis.
Departs: 18 Dec 2026
Includes taxes and fees
2. St Maarten
This Caribbean island has two distinctly different European flavours – Dutch in the south and French in the north. But what both have in common is sugar-white beaches and crystal-clear waters.
Though unique and beautiful, St Maarten is tiny and can be expensive, so it’s best visited on a multi-island cruise. Ships dock in Philipsburg, the capital, on the more developed Dutch side. Here, you’ll find colourful, colonial-style buildings, excellent duty-free shops, and lively beach resorts.
The French side is more rustic, with outdoor markets, wooden boats bobbing in the harbour, and secluded stretches of sand.
You can take a coastal hike between bays – or you might prefer a catamaran cruise, which typically anchors at one or more of the island’s beaches for swimming and snorkelling.
St Maarten is also a place for foodies, with over 300 restaurants and unique fusion cuisine, earning it the reputation of the ‘culinary capital of the Caribbean’.
3. Curaçao
The teeny Dutch island of Curaçao is one of the most colourful Caribbean islands, with tempting coves and expansive coral reefs, rich with marine life.
Curaçao’s cruise port is in the capital city, Willemstad, where you’ll find vivid street murals, the historic Pietermaai Cathedral, and a waterfront lined with pastel-painted Dutch colonial buildings.
The city is divided into two parts, connected by a pontoon. This is lit up at night, making it an enjoyable place for a stroll. It’s also the place to pick up a bottle of the famous Blue Curaçao (an orange-flavoured liqueur) as a souvenir.
Doctor’s Bay is the island’s top snorkelling spot – home to a shipwrecked tugboat teeming with turtles, rays, and tropical fish. Or, for diving, head to Blue Bay Beach, which has a stunning stretch of sand, too. Watersport lovers can enjoy jet-skiing, speedboat rides, and kayaking around the island’s coast.
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Oceania Cruises Panama City to Miami*
Panama City - Cartagena - Santa Marta - Oranjestad - Willemstad - Falmouth - George Town - Miami
USA, Colombia, Cayman Islands & 4 more | 10 days
Exceptional Savings - up to 50% off select sailings, gourmet speciality dining, unlimited WiFi and more.
The finest cuisine at sea®. Award-winning itineraries. Small ship luxury™.
Departs: 15 Mar 2027
Includes taxes and fees
4. St Lucia
St Lucia is a great place to enjoy nature. Its headline attraction is the Pitons – towering twin mountains clothed in tropical rainforest. At their feet are volcanic beaches with black sand, lush greenery, and some of the best coral reefs in the Caribbean.
When cruising to St Lucia, most ships dock in the capital city of Castries on the northwest coast. This popular city boasts beautiful architecture, lively markets, and clear waters.
Once you’ve explored Castries, you’ll find a lot of the island’s most popular attractions on the southwest coast. You can hike the trails on the slopes of the Pitons and sample some of St Lucia’s signature seafood in the fishing village, Soufriere.
It’s also worth paying a visit to the lovely Marigot Bay, the most famous cove on the island, where in the 18th century, the English fought the French for control. You can snorkel around Pigeon Island, enjoy scuba diving amongst the reefs, or book a whale watching tour to try and spot humpback and pilot whales.
5. Dominica
The unspoiled island of Dominica is a nature lover’s paradise, with rugged mountains, tropical rainforests, and tumbling waterfalls.
With no international airport, cruising is the best way to reach this off-the-beaten-track haven. You’ll dock in the capital, Roseau, where colourful timber houses have European-style porticoes and verandas.
For those interested in culture and tradition, Dominica is home to the indigenous Kalinago people, and a day trip to the model village in their territory on the east coast will offer a glimpse into their way of life.
Dominica is also known as one of the Caribbean’s most adventurous islands. You can admire the photogenic twin Trafalgar Falls or try canyoning in Titou Gorge. Or, why not head to Morne Trois Pitons National Park and hike to the boiling lake in the crater of an active volcano?
Dominica has great scuba diving, too, and on a catamaran trip off the coast, you can look for dolphins and sperm whales.
6. Dominican Republic
Sandy beaches, lush rainforest, majestic mountains, and seductive Spanish colonial towns…the Dominican Republic has plenty to explore.
Cruises regularly come into Amber Cove on the north coast (named after the famous stone produced here). The characterful resort town of Puerto Plata is nearby and boasts long stretches of white sand, fringed with palm trees. It also features the Caribbean’s only cable car, which you can ride up Mount Isabel de Torres for amazing coastal views.
For watersports, head to Cabarete Beach, a world-famous spot for windsurfing and kiteboarding. Nature lovers might enjoy taking a boat trip to try to spot humpback whales. And, for those who fancy a Caribbean adventure, a hike through the Waterfalls of Damajagua offers an unforgettable jungle experience.
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Oceania Cruises Miami to Miami*
Miami - Charlotte Amalie - St. John's - Philipsburg - San Juan - Puerto Plata - Great Stirrup Cay
USA, Antigua and Barbuda, Dominican Republic & 4 more | 10 days
Exceptional Savings - up to 50% off select sailings, gourmet speciality dining, unlimited WiFi and more.
The finest cuisine at sea®. Award-winning itineraries. Small ship luxury™.
Departs: 13 Feb 2027
Includes taxes and fees
7. Turks and Caicos
A 40-island archipelago in the Atlantic Ocean, the Turks and Caicos Islands are what Caribbean dreams are made of…think secluded white sand beaches and sparkling turquoise seas.
A trip to Turks and Caicos isn’t complete without a visit to Grand Turk, one of its most beautiful islands, where wild horses and donkeys roam. It’s possible to fly here from Turks and Caicos, but most agree it’s easier and more enjoyable to go by cruise.
Surrounded by a ring of beaches and translucent water, Grand Turk is a great place for watersports. You can snorkel with stingrays, watch turtles, or scuba dive to see a dramatic underwater wall.
Time is also well spent in Cockburn Town, the capital city of the archipelago. Here, you’ll find Bermudian-style buildings and the Turks and Caicos Museum.
And, for an unusual adventure, it’s worth taking a four-wheel drive safari to see flamingos in the islands’ salt ponds.
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Fort Lauderdale - Princess Cays - Amber Cove - Grand Turk - Nassau
Dominican Republic, The Bahamas & Turks and Caicos | 7 nights
Departs: 10 Oct 2026
Includes taxes and fees
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Port Canaveral - Nassau - Princess Cays - Amber Cove - Grand Turk
USA, Dominican Republic, The Bahamas & 1 more | 7 nights
Departs: 11 Oct 2026
Includes taxes and fees
8. Cuba
Cruises to Cuba often dock in the characterful, cultural capital of Havana, which offers a Caribbean city experience like no other.
In the old quarter of this UNESCO World Heritage-listed city, crumbling pastel-coloured Spanish-colonial mansions rub shoulders with murals of revolutionaries. There’s also no shortage of hole-in-the-wall bars pulsing with live jazz and selling rum and cigars.
It’s popular to explore Havana in a vintage car from the 1950s. Why not drive along the city’s famous seafront promenade (the Malecon) and absorb the laid-back vibe of the city?
For those looking to get to the heart of the island’s history, it’s worth heading to Revolution Square, which is dedicated to Fidel Castro’s uprising in the 1950s. Or, follow in the footsteps of one of Havana’s most colourful characters, Ernest Hemingway, by visiting his old home and ending the day with a mojito in one of his favourite bars.
If you’d like to make like Frank Sinatra and Marlon Brando, a cabaret show at The Tropicana or The Havana Café is a must-see, too.
Final thoughts…
For many of us, these laid-back, sunny islands with flour-soft sands and sparkling azure waters are what dreams are made of – and a cruise can be one of the best ways to see them.
From Dominica and Antigua to Curaçao and the Dominican Republic, whatever tropical destinations are on your wish list, chances are, there’ll be a cruise to take you there.
There are also many unique benefits to cruising; the key one being that they allow you to visit multiple destinations in a single trip, without the hassle of catching extra flights.
For more ideas for your next escape, why not visit our travel section? Here, you’ll browse articles like 5 luxurious Caribbean cruises of a lifetime and 20 best places to cruise month by month. Or, you can browse Caribbean cruise holiday deals below.
What appeals to you most about cruising in the Caribbean? Are you tempted by any of the destinations above? We’d love to hear from you in the comments below.
Nicola Grihault is a contributor to Rest Less. She became a member in 2021 and joined the editorial team in Jan 2023. She has a psychology degree, TEFL certificate, and a licence to practise homoeopathy. Nicola covers various lifestyle topics, with a special interest in travel, personal development, and alternative health. She spent 20+ years as a freelance travel writer, visiting 50 countries, and still writes about Mauritius for national newspapers, magazines, and websites. In her spare time, Nicola walks, reads, cooks, and attempts to keep up with yoga! She’s fascinated by mountains, deserts, and snow, and loves rom-coms.
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