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Caribbean Tours & Trips 2020/2021

Find the right tour for you through Caribbean. We've got 139 tours going to Caribbean, starting from just 3 days in length, and the longest tour is 28 days. The most popular month to go is November, which has the most number of tour departures.

139 Caribbean trips with 811 reviews

  • Best of Cuba

    "We took the 15 day,beginning May 5th 2016, "Best of Cuba" Tour, and had Yanet Cabrera..."
    destinations
    Havana, Cienfuegos, Trinidad, Camaguey, Santiago de Cuba, Baracoa
    age range
    15 to 99 year olds
    Travel style
    Christmas & New Year
    operator
    Intrepid Travel
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    Tour length
    15 days
    Price per day
    $130
    From
    US$1,950
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  • Beautiful Cuba

    "I’d been to Cuba twice before this tour and did the all-inclusive thing. Going..."
    destinations
    Havana, Soroa, Vinales, Trinidad, Cienfuegos, Santa Clara
    age range
    15 to 99 year olds
    Travel style
    Christmas & New Year
    operator
    Intrepid Travel
    Book With Flexibility. If your plans change, choose a new date or tour with the same tour operator.
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    Tour length
    8 days
    Price per day
    $171
    From
    US$1,370
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  • Original Cuba - 8 Days

    210 reviews
    AWARD WINNER
    "I had a fantastic time in Cuba during my tour that was led by Yoanis. I experienced..."
    destinations
    Havana, Vinales, Cienfuegos, Trinidad, Santa Clara
    age range
    18 to 99 year olds
    Country Region
    Central Cuba
    Travel style
    Local Living, Christmas & New Year+1 more
    operator
    Cuban Adventures
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    Tour length
    8 days
    Price per day
    $63
    From
    US$503
    • +$218 local payments
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  • 15 Day Original

    "to select tourradar and cuban adventures was the best decision we could do. We were..."
    destinations
    Havana, Cienfuegos, Santa Clara, Trinidad, Camaguey, Santiago de Cuba, Baracoa
    age range
    18 to 99 year olds
    Travel style
    Local Living, Christmas & New Year+1 more
    operator
    Cuban Adventures
    Book With Flexibility. If your plans change, choose a new date or tour with the same tour operator.
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    Tour length
    15 days
    Price per day
    $70
    From
    US$1,051
    • +$272 local payments
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  • Learn Spanish, Dance & Culture - Cuba 14 Days

    "My trip to Cuba with Jakera turned out to be a life changing experience! I went with..."
    destinations
    Havana
    age range
    18 to 99 year olds
    Country Region
    Western Cuba
    Travel style
    Christmas & New Year
    operator
    Bucanero Adventure
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    Tour length
    14 days
    Price per day
    $59
    From
    US$831
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  • Best of Cuba in 10 days

    "yunior was an excellent guide, showed the real Cuban side of Trinidad with the history..."
    destinations
    Havana, Trinidad, Varadero
    age range
    1 to 99 year olds
    Travel style
    Local Guide, Local Living, In-depth Cultural, Christmas & New Year+2 more
    operator
    MiCuba
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    -10%
    Tour length
    10 days
    Price per day
    $75
    From
    $837
    US$753
    You save: $83
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  • Essential Cuba

    "We really enjoyed our trip of Cuba and our fellow travellers were great fun."
    destinations
    Havana, Soroa, Vinales, Trinidad, Cienfuegos
    age range
    15 to 99 year olds
    Travel style
    Coach / Bus, Christmas & New Year+1 more
    operator
    Peregrine Adventures
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    Tour length
    9 days
    Price per day
    $259
    From
    US$2,332
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  • 15 Day Cuba Group Tour - Majestic Cuba

    "Yohandro was the best and we are still friends."
    destinations
    Havana, Cienaga de Zapata NP, Cienfuegos, Santa Clara, Trinidad, Camaguey, Santiago de Cuba, Baracoa+2 more
    age range
    15 to 70 year olds
    Travel style
    Family, Christmas & New Year+1 more
    operator
    Locally Sourced Cuba Tours
    Book With Flexibility. If your plans change, choose a new date or tour with the same tour operator.
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    Tour length
    15 days
    Price per day
    $97
    From
    US$1,456
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  • Cuba Highlights

    destinations
    Havana, Santiago de Cuba, Camaguey, Ciego de Avila, Trinidad, Topes de Collantes, Santa Clara, Cienfuegos, Playa Giron, Playa Larga, Vinales+6 more
    age range
    15 to 99 year olds
    operator
    Peregrine Adventures
    Book With Flexibility. If your plans change, choose a new date or tour with the same tour operator.
    If you change your travel plans after you book, convert what you paid to credit. Apply your credit to future tours run by the same tour operator.
    Tour length
    14 days
    Price per day
    $265
    From
    US$3,713
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  • Cuba on a Shoestring

    "Very lucky to have had a fabulous group on this tour. The itinerary was great and..."
    destinations
    Havana, Vinales, Trinidad, Santa Clara
    age range
    15 to 99 year olds
    Travel style
    Adventure, Christmas & New Year+1 more
    operator
    Intrepid Travel
    Book With Flexibility. If your plans change, choose a new date or tour with the same tour operator.
    If you change your travel plans after you book, convert what you paid to credit. Apply your credit to future tours run by the same tour operator.
    Tour length
    8 days
    Price per day
    $103
    From
    US$826
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  • Tour length
    11 days
    Price per day
    $267
    From
    $3,465
    US$2,934
    You save: $530
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  • Cycle Cuba: West

    "I had an exceptional trip with intrepid on my recent cycle cuba tour. Our tour guide..."
    destinations
    Havana, Soroa, Las Terrazas, Vinales, Cayo Juti­as, Consolacion del Sur
    age range
    15 to 99 year olds
    Country Region
    Western Cuba
    Travel style
    Adventure
    operator
    Intrepid Travel
    Book With Flexibility. If your plans change, choose a new date or tour with the same tour operator.
    If you change your travel plans after you book, convert what you paid to credit. Apply your credit to future tours run by the same tour operator.
    Tour length
    7 days
    Price per day
    $164
    From
    US$1,147
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  • 6 Day Western Cuba

    "From tourguide perspective, my experience was spectacular. Ivan is an impeccable..."
    destinations
    Havana, Las Terrazas, Soroa, Vinales
    age range
    18 to 99 year olds
    Country Region
    Western Cuba
    Travel style
    Local Living, Christmas & New Year+1 more
    operator
    Cuban Adventures
    Book With Flexibility. If your plans change, choose a new date or tour with the same tour operator.
    If you change your travel plans after you book, convert what you paid to credit. Apply your credit to future tours run by the same tour operator.
    Tour length
    6 days
    Price per day
    $58
    From
    US$347
    • +$218 local payments
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  • Cuban Rhythms: Rum & Fun

    "Amazing experience! Great tour guide"
    destinations
    Havana, Santa Clara, Trinidad, Vinales, Cayo Levisa, Las Terrazas
    age range
    18 to 39 year olds
    Travel style
    Local Living, Christmas & New Year+1 more
    operator
    G Adventures
    Tour length
    8 days
    Price per day
    $90
    From
    US$720
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  • Cuba Explorer

    "Well organised, great mix of organised activities and free time"
    destinations
    Havana, Santiago de Cuba, Camaguey, Trinidad, Playa Ancon, Santa Clara
    age range
    15 to 99 year olds
    Country Region
    Central Cuba
    Travel style
    Adventure
    operator
    Intrepid Travel
    Book With Flexibility. If your plans change, choose a new date or tour with the same tour operator.
    If you change your travel plans after you book, convert what you paid to credit. Apply your credit to future tours run by the same tour operator.
    Tour length
    10 days
    Price per day
    $140
    From
    US$1,399
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Highlights

  • Put your dancing shoes on and move to the seductive rhythms of salsa, in one of Havana’s many sizzling salsa clubs.
  • Enjoy a sundowner, and listen to the hypnotic Afro-Cuban rhythm of Son music, in the colonial inspired city of Trinidad.
  • Experience spine-tingling excitement, as you listen to the tales of Che Guevara’s bravado at Santa Clara, Cuba.
  • Go swimming with sea turtles, and discover the secrets of pristine coral reefs, while snorkelling in the crystal clear archipelago that surrounds the British Virgin Islands.
  • Enjoy a heart-pounding and vibrant drum lesson by indigenous Rastafarian communities, in the heart of Jamaica’s verdant inland wilderness.
  • Feast your eyes on natural wonders, and listen to the alluring voices of nature as you follow the Waitukubuli National Trail in Dominica.
  • Discover the secrets of Haiti’s indomitable spirit, its vibrant culture and Voodoo folklore in the alleys and streets of Port-au-Prince.
  • Hit the waves at Puerto Rico’s Rincon Island, the Mecca of Caribbean surfing.

Tips

  • Get an intimate introduction to Cuban customs and traditional meals, by spending some time at a Cuban home stay.
  • Go ahead and try some Varadero rum and Havana Club rum, while in Cuba.
  • You can shop for high quality Cuban cigars that come in ornate cigar boxes.
  • Buy decorative pieces and amber jewellery in Dominica.
  • Sample some of Jamaica’s famous and flavoursome jerk chicken.
  • Head to Jamaica’s Kingston Town for the best live reggae music and calypso.
  • Haiti’s Iron Market is an excellent place to shop for paintings and other handicrafts in the local ‘naif’ style.
  • Most of the locals understand Spanish or English (Spanglish) on the islands of Puerto Rico, so you won’t find it difficult to communicate.

Caribbean Tours & Trips Reviews

  • "We visited lots of different cities, all different in their own way (a day extra..."
    Best of Cuba
  • "An excellent 8 day tour which had a good cross section of town & country. The casa’s..."
    Beautiful Cuba
  • "I had a fantastic time in Cuba during my tour that was led by Yoanis. I experienced..."
    Original Cuba - 8 Days
  • "Yoanis is an amazing tour guide who will go out of his way to make sure you get the..."
    15 Day Original
  • "The tour package I took (which was 2 weeks but spent most of the time in Havana)..."
    Learn Spanish, Dance & Culture - Cuba 14 Days
  • "He is very funny and knowledgeable about his area. Enjoyed it."
    Best of Cuba in 10 days