Best Caribbean Tours & Holidays 2023/2024

Whether it’s rum and cigars, sun and surf or dining and dancing, nowhere does good vibes quite like the Caribbean.

Jamaican rum or a Cuban cigar? Reggae beats or salsa rhythms? Trekking across volcanoes or relaxing with sand between your toes? These are the only questions you need to answer while kicking back on the brilliant beaches of the Caribbean. Spend days sailing from island to island, exploring uninhabited Cays and snorkelling for marine life. Fill the nights with food and music, eat fresh fish and jerked chicken, listen to Bob Marley and dance the cha-cha (though maybe not all at once). From Havana to Jamaica, everything in between is pure indulgence.

Our tours in the Caribbean

Beautiful Cuba

8 Days From 1547

Escape to Cuba on an adventure to this exotic Caribbean island and explore the sultry...

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Best of Cuba

15 Days From 1963

Escape to Cuba on an exotic getaway through the sizzling streets of sultry Havana, soak...

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Premium Cuba

9 Days From 3507

Escape to Cuba on a Premium adventure and explore the old-world charm of Havana,...

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Ages 18 to 29

One Week in Cuba

8 Days From 1454

Go back in time on the streets of Cuba on this trip that takes you from Havana to Playa...

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Cycle Cuba: East

8 Days From 1841

Explore laidback eastern Cuba on a two-wheeled round-trip adventure from Havana. Cycle...

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Tailor-Made trips

Take four or more on an exclusive trip and tailor your itinerary

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Cycle Cuba: West

7 Days From 1843

Explore laidback Cuba on a two-wheeled round-trip adventure from Havana. Cycle along...

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Cuba Family Holiday

11 Days From 2755

Travel to Cuba and uncover the many layers of this intriguing nation as a family. Visit...

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Premium Mexico & Cuba

23 Days From 14615

In 23 incredible days you’ll delight in the culture, cuisine and colours of Mexico on...

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Discover Mexico & Cuba

22 Days From 5875

Adventure with Intrepid Travel through Mexico and Cuba on a 22-day Lonely Planet...

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Best of Mexico & Cuba

22 Days From 9545

Embark on an adventure through Mexico and Cuba that spends time in Mexico City, Oaxaca,...

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Cycle Cuba

14 Days From 3930

Cycle along rural roads, meet friendly locals, swim in the warm seas, explore white...

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Cuba Highlights

8 Days From 1373

See eight days of Cuba highlights, from the colourful streets of Old Havana to Vinales,...

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Cuba

Jamaica

Highlights of the Caribbean

Montego Bay

Mo’Bay, Jamaica’s second city, is famous for its steady reggae rhythms and tasty jerked chicken. By day, shop in the Charles Garden Market or take a walk down historical Sam Sharpe Square, then spend the night dining, drinking and dancing in The Hip Strip, the Caribbean’s party-central.

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Canarreos Archipelago

South of the Cuban mainland is the Canarreos Archipelago, made up of about 350 islands. Sail your way through clear waters, stopping at beaches for cocktails and island-style barbeques. Look out for the iguanas of Cayo Rico, the monkeys of Cayo Cantiles, the manta rays off Cayo Alcatraz, and maybe even a turtle or two.

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Reviews

What to see in 7-10 days in the Caribbean

A short stay in the Caribbean means you’ll likely want to focus your travels in one place. Spread yourself too thin and you might miss out on the best experience the region has to offer – that sense of calm at the end of a day of relaxation. If it’s mostly sun and sand you’re after, then you could jump in a boat and sail around the archipelagos of the Bahamas looking for the best place to throw down a towel. If you want to party till the sun comes up, then head to Jamaica, with Montego Bay and Kingston home to Rastafarian reggae beats that’ll keep you dancing. If it’s more the salsa rhythms that get your feet moving, you might prefer Cuba. Take in the exciting nightlife and old-world charm of Havana or discover the diverse spread of wildlife around the Canarreos Peninsula.

Tailor-Made trips

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What to see in 3 weeks in the Caribbean

Three weeks in the Caribbean means you’ll have more than a few chances to rest up on the white sands of paradise. Island-hop from the cays of the Bahamas to the cayos of Cuba, or snorkel your way past the shores of Costa Rica and Panama. With flights getting you from Havana to Kingston in under an hour, it’s easy to combine two or more countries. You could trek your way through the forests and caves of the Sierra Maestra mountain range with plenty of time left to explore the Rastafari villages of Montego Bay.

If you’d rather use your time to savour the character of just one country, then hit the cities and towns of Cuba. You could start by exploring the colonial streets of Camaguey on taxi-bike and end by rolling a cigar with the tobacco farmers in Pinar del Rio, with just enough time to see all the sights in between.

Tailor-Made trips

Take four or more on an exclusive trip and tailor your itinerary

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What to see in 6 weeks in the Caribbean

With six weeks in the Caribbean, you’ll want to have your sea legs ready. Set off on a sailing trip in the Bahamas and you’ll never be far from a cool beach and a warm breeze. You’ll also find a variety of marine wildlife along the way, from turtles to manta rays. But don’t mistake paradise with monotony. Each island has unique features to explore, whether it’s the nesting sites of loggerhead turtles on Cayo Largo del Sur or the naturally formed rock-spa dubbed Bubbly Pool on Diamond Cay.

If six weeks sounds like a long time to lie on a beach, then look at combining your Caribbean getaway with the jungles of Belize, the Mayan ruins of Mexico, or the volcanoes of Costa Rica.

Central American Adventure

33 Days From 4655

Tour jungle ruins and Caribbean coastline on a 33-day adventure to Mexico, Belize,...

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Tailor-Made trips

Take four or more on an exclusive trip and tailor your itinerary

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Responsible travel

Intrepid is committed to travelling in a way that is respectful of local people, their culture, local economies and the environment. It's important to remember that what may be acceptable behaviour, dress and language in your own country, may not be appropriate in another. Please keep this in mind while travelling.

How we're giving back

In Caribbean, we stay in locally run accommodation including guesthouses, smaller-scale hotels and homestays in an effort to support the local economies. We also visit locally-run restaurants and markets where travellers will have opportunities to support local businesses and purchase handicrafts created by local artisans.