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Caribbean Tours in Winter 2019

Caribbean Tours in Winter 2019

Searching for tours in Caribbean during Winter 2019? Look no further, as our tours of Caribbean will walk you through exceptional destinations such as Cuba and Dominican Republic. Explore and discover new cultures

Up to 75% off - across the globe!
ends on 24 Jan 2019
130 trips in Caribbean in December, January and February
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130 trips in Caribbean in December, January and February

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  • 10 Day Cuba Group Tour - Vivacious Cuba

    "We booked the 10 day Vivacious Cuba Group tour and had an amazing trip. The tour..."
    Instant Booking
    destinations
    Havana, Cienaga de Zapata NP, Cienfuegos, Santa Clara, Trinidad, Vinales+5 more
    starts/ ends in
    Havana / Havana
    age range
    15 to 70 year olds
    accommodation
    Home-stay, Guesthouse
    transport
    Private Vehicle
    Country Region
    Cuba for US Citizens
    Travel style
    Christmas & New Year
    operator
    Locally Sourced Cuba Tours
    -15%
    Duration
    10 days
    Price per day
    $71
    From
    $830
    US$705
    You save $125
    1 Dec 2019
    8 spaces left
    8 Dec 2019
    8 spaces left
    View tour
    More information
  • Cuban Rhythms

    "Fun, rum and a flavour of cuba"
    Instant Booking
    destinations
    Havana, Santa Clara, Trinidad, Vinales, Cayo Levisa, Las Terrazas+4 more
    starts/ ends in
    Havana / Havana
    age range
    18 to 39 year olds
    accommodation
    Hotel, Home-stay
    transport
    Boat, Private Vehicle
    Travel style
    Local Living, Christmas & New Year+1 more
    operator
    G Adventures
    -18%
    Duration
    8 days
    Price per day
    $97
    From
    $949
    US$775
    You save $175
    1 Dec 2019
    10+ spaces left
    5 Dec 2019
    10+ spaces left
    View tour
    More information
  • 15 Day Original

    "I can only say good things about tour,great wonderful exciting.It was a small group..."
    destinations
    Havana, Cienfuegos, Santa Clara, Trinidad, Camaguey, Santiago de Cuba, Baracoa+5 more
    starts/ ends in
    Havana / Havana
    age range
    18 to 99 year olds
    accommodation
    Guesthouse
    transport
    Private Vehicle
    Travel style
    Local Living, Christmas & New Year+1 more
    operator
    Cuban Adventures
    Duration
    15 days
    Price per day
    $59
    From
    US$890
    • +$250 local payments
    6 Dec 2019
    10+ spaces left
    13 Dec 2019
    10+ spaces left
    View tour
    More information
  • Best of Cuba

    "Our guide, Roger (? sp.), was knowledgeable, had a lovely sense of humour, and was..."
    Instant Booking
    destinations
    Havana, Cienfuegos, Trinidad, Camaguey, Santiago de Cuba, Baracoa+4 more
    starts/ ends in
    Havana / Havana
    age range
    15 to 99 year olds
    accommodation
    Hotel, Guesthouse
    transport
    Coach / Bus, Local Transport, Private Vehicle, Plane+3 more
    Travel style
    Christmas & New Year
    operator
    Intrepid Travel
    -29%
    Duration
    15 days
    Price per day
    $110
    From
    $2,325
    US$1,652
    You save $673
    1 Dec 2019
    10+ spaces left
    8 Dec 2019
    10+ spaces left
    View tour
    More information
  • 8 Day Cuba Group Tour - Lively Cuba

    "It was good. I believe I did this 6 months ago."
    Instant Booking
    destinations
    Havana, Cienaga de Zapata NP, Cienfuegos, Santa Clara, Trinidad, Vinales+5 more
    starts/ ends in
    Havana / Havana
    age range
    15 to 70 year olds
    accommodation
    Home-stay, Guesthouse
    transport
    Private Vehicle
    Country Region
    Cuba for US Citizens
    Travel style
    Christmas & New Year
    operator
    Locally Sourced Cuba Tours
    -15%
    Duration
    8 days
    Price per day
    $75
    From
    $711
    US$604
    You save $107
    1 Dec 2019
    6 spaces left
    8 Dec 2019
    6 spaces left
    View tour
    More information
  • Cuba Colonial

    "Awesome tour!! We had the best CEO, Nadya, such a sweet girl and always willing to..."
    Instant Booking
    destinations
    Havana, Santa Clara, Trinidad, Camaguey, Santiago de Cuba, Baracoa+4 more
    starts/ ends in
    Havana / Havana
    age range
    12 to 70 year olds
    accommodation
    Hotel, Home-stay
    transport
    Private Vehicle, Plane
    Travel style
    Adventure, Christmas & New Year+1 more
    operator
    G Adventures
    -18%
    Duration
    15 days
    Price per day
    $125
    From
    $2,299
    US$1,876
    You save $423
    7 Dec 2019
    10+ spaces left
    14 Dec 2019
    10+ spaces left
    View tour
    More information
  • Cuba Highlights

    13 day in-depth cultural tour through Havana, Santiago de Cuba, Camaguey and 8 other destinations in Cuba

    Instant Booking
    destinations
    Havana, Santiago de Cuba, Camaguey, Ciego de Avila, Trinidad, Topes de Collantes, Santa Clara, Cienfuegos, Playa Giron, Playa Larga, Vinales+10 more
    starts/ ends in
    Havana / Havana
    age range
    15 to 99 year olds
    accommodation
    Hotel, Guesthouse
    transport
    Coach / Bus, Private Vehicle, Plane+2 more
    Travel style
    Christmas & New Year
    operator
    Peregrine Adventures
    -14%
    Duration
    13 days
    Price per day
    $286
    From
    $4,310
    US$3,724
    You save $586
    14 Dec 2019
    10+ spaces left
    28 Dec 2019
    10+ spaces left
    View tour
    More information
  • Essential Cuba

    "Our Cuba trip was fantastic, the tour leader Will was so knowledgeable and passionate...."
    Instant Booking
    destinations
    Havana, Soroa, Vinales, Trinidad, Cienfuegos+3 more
    starts/ ends in
    Havana / Havana
    age range
    15 to 99 year olds
    accommodation
    Hotel, Guesthouse
    transport
    Private Vehicle
    Travel style
    Coach / Bus, Christmas & New Year+1 more
    operator
    Peregrine Adventures
    -14%
    Duration
    9 days
    Price per day
    $297
    From
    $3,095
    US$2,674
    You save $421
    14 Dec 2019
    10+ spaces left
    21 Dec 2019
    10+ spaces left
    View tour
    More information
  • Western Cuba

    "Had an amazing time, saw an amazing place and met some amazing people!!! Natalia..."
    Instant Booking
    destinations
    Havana, Las Terrazas, Vinales, Soroa+2 more
    starts/ ends in
    Havana / Havana
    age range
    15 to 99 year olds
    accommodation
    Guesthouse
    transport
    Private Vehicle
    Country Region
    Western Cuba
    Travel style
    Christmas & New Year
    operator
    Intrepid Travel
    -29%
    Duration
    7 days
    Price per day
    $115
    From
    $1,126
    US$804
    You save $322
    8 Dec 2019
    10+ spaces left
    12 Dec 2019
    10+ spaces left
    View tour
    More information
  • 8 Day Original

    138 reviews
    AWARD WINNER
    "We travel a lot and this is the best tour we have ever been on. The tour, the transport,..."
    destinations
    Havana, Vinales, Cienfuegos, Trinidad, Santa Clara+3 more
    starts/ ends in
    Havana / Havana
    age range
    18 to 99 year olds
    accommodation
    Guesthouse
    transport
    Private Vehicle
    Country Region
    Central Cuba, Cuba for US Citizens+1 more
    Travel style
    Local Living, Christmas & New Year+1 more
    operator
    Cuban Adventures
    Duration
    8 days
    Price per day
    $53
    From
    US$425
    • +$200 local payments
    5 Dec 2019
    10+ spaces left
    12 Dec 2019
    10+ spaces left
    View tour
    More information
  • Dominican Republic – Heart & Soul of the Caribbean

    "Accommodations are quite rustic and a bit loud as you are staying right next to a..."
    Instant Booking
    destinations
    Playa Las Canas
    starts/ ends in
    Playa Las Canas / Playa Las Canas
    age range
    15 to 80 year olds
    accommodation
    Lodge
    transport
    Private Vehicle
    operator
    Discover Corps
    Duration
    8 days
    Price per day
    $299
    From
    US$2,395
    You save $100
    26 Dec 2019
    10+ spaces left
    1 Feb 2020
    10+ spaces left
    View tour
    More information
  • Cuba on a shoestring

    "Cuba on a Shoestring - The tour was generally great and was all I expected and more...."
    Instant Booking
    destinations
    Havana, Vinales, Playa Giron, Playa Larga, Cienfuegos, Trinidad, Playa Ancon, Santa Clara+6 more
    starts/ ends in
    Havana / Havana
    age range
    15 to 99 year olds
    accommodation
    Guesthouse
    transport
    Private Vehicle
    Travel style
    Adventure, Christmas & New Year+1 more
    operator
    Intrepid Travel
    -18%
    Duration
    8 days
    Price per day
    $101
    From
    $984
    US$808
    You save $176
    7 Dec 2019
    10+ spaces left
    14 Dec 2019
    10+ spaces left
    View tour
    More information
  • Learn Spanish, Dance & Culture - Cuba 28 days

    "Once in a lifetime experience living Cuban lifestyle for a month.. Spanish lessons..."
    Instant Booking
    destinations
    Havana, Vinales
    starts/ ends in
    Havana / Havana
    age range
    18 to 99 year olds
    accommodation
    Hostel, Guesthouse
    transport
    Local Transport
    Country Region
    Vinales, Western Cuba, Cuba for US Citizens+1 more
    Travel style
    In-depth Cultural, Christmas & New Year+1 more
    operator
    Bucanero Adventure
    Duration
    28 days
    Price per day
    $54
    From
    US$1,517
    You save $63
    1 Dec 2019
    10 spaces left
    15 Dec 2019
    10 spaces left
    View tour
    More information
  • Cuba by Bike

    "Jackson was an amazing guide! Learned so much about Cuba past and present. Bikes..."
    destinations
    Havana, San Diego de los Banos, Vinales, Cayo Levisa, Las Terrazas, Cienfuegos, Guajamico, Trinidad, Topes de Collantes, Santa Clara+9 more
    starts/ ends in
    Havana / Havana
    age range
    16 to 80 year olds
    accommodation
    Hotel, Home-stay
    transport
    Bicycle, Private Vehicle
    Country Region
    Cuba for US Citizens
    Travel style
    Adventure, In-depth Cultural, Historical+2 more
    operator
    World Expeditions
    Duration
    12 days
    Price per day
    $224
    From
    US$2,687
    You save $112
    10 Dec 2019
    10+ spaces left
    9 Jan 2020
    10+ spaces left
    View tour
    More information
  • Best of Cuba Westbound

    "Excellent tour would recommend it, but not for everyone, need to be open minded."
    Instant Booking
    destinations
    Havana, Baracoa, Guantanamo, Santiago de Cuba, Camaguey, Trinidad, Playa Ancon, Topes de Collantes, Santa Clara, Cienfuegos, Playa Giron+9 more
    starts/ ends in
    Havana / Havana
    age range
    15 to 99 year olds
    accommodation
    Guesthouse
    transport
    Local Transport, Private Vehicle, Plane+2 more
    Travel style
    Adventure, Christmas & New Year+1 more
    operator
    Intrepid Travel
    -29%
    Duration
    15 days
    Price per day
    $111
    From
    $2,337
    US$1,664
    You save $673
    5 Dec 2019
    10+ spaces left
    12 Dec 2019
    10+ spaces left
    View tour
    More information
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Caribbean Tours and Trips Reviews

  • "A great way to see Cuba, loved staying in Casas, the perfect way to get the real..."
    10 Day Cuba Group Tour - Vivacious Cuba
  • "By far the best holidays I've ever had. Cuba is beautiful, musical, and addictive!..."
    Cuban Rhythms
  • "Guide: David I really liked my trip to Cuba, and I can say the guide makes the difference!..."
    15 Day Original
  • "Our guide, Roger (? sp.), was knowledgeable, had a lovely sense of humour, and was..."
    Best of Cuba
  • "Our tour gave us a feel for Cuba which I don't think that we would have got on our..."
    8 Day Cuba Group Tour - Lively Cuba
  • "Awesome tour!! We had the best CEO, Nadya, such a sweet girl and always willing to..."
    Cuba Colonial