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Winter Tours & Vacation Packages Caribbean

Winter Tours & Vacation Packages Caribbean

Searching for tours in Caribbean during Winter 2020? Look no further, as our tours of Caribbean will walk you through exceptional destinations such as Cuba and Virgin Island, British. Explore and discover new cultures

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42 Caribbean holiday packages in December, January and February

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  • Original Cuba - 8 Days

    184 reviews
    AWARD WINNER
    "Great experience, educational, entertaining!"
    Instant Booking
    Just $99 now
    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
    $54
    From
    US$433
    • +$200 local payments
    3 Dec 2020
    10+ spaces left
    10 Dec 2020
    10+ spaces left
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    More information
  • Best of Cuba

    "Very comprehensive, knowledgeable tour guide who was helpful and lovely and had us..."
    Instant Booking
    Just $99 now
    destinations
    Havana, Cienfuegos, Trinidad, Camaguey, Santiago de Cuba, Baracoa+4 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
    Christmas & New Year
    operator
    Intrepid Travel
    -29%
    Duration
    15 days
    Price per day
    $97
    From
    $2,069
    US$1,462
    You save: $607
    6 Dec 2020
    10+ spaces left
    13 Dec 2020
    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
    Just $99 now
    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
    $210
    From
    $2,193
    US$1,887
    You save: $306
    12 Dec 2020
    10+ spaces left
    19 Dec 2020
    10+ spaces left
    View tour
    More information
  • 15 Day Original

    "Great tour with a real local focus. 15 day original tour is great value for money"
    Just $99 now
    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
    $60
    From
    US$907
    • +$250 local payments
    4 Dec 2020
    10+ spaces left
    11 Dec 2020
    10+ spaces left
    View tour
    More information
  • Learn Spanish, Dance & Culture - Cuba 14 Days

    "The tour package I took (which was 2 weeks but spent most of the time in Havana)..."
    Instant Booking
    Just $99 now
    destinations
    Havana
    starts/ ends in
    Havana / Havana
    age range
    18 to 99 year olds
    accommodation
    Hostel
    Country Region
    Western Cuba, Cuba for US Citizens+1 more
    operator
    Bucanero Adventure
    Duration
    14 days
    Price per day
    $57
    From
    US$793
    You save: $25
    6 Dec 2020
    10 spaces left
    20 Dec 2020
    10 spaces left
    View tour
    More information
  • Best of Cuba Westbound

    "Beautiful country, fantastic tour mates, the casas were much better than I had accepted,..."
    Instant Booking
    Just $99 now
    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
    $97
    From
    $2,069
    US$1,462
    You save: $607
    3 Dec 2020
    10+ spaces left
    10 Dec 2020
    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
    Just $99 now
    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
    Private Vehicle, Plane
    operator
    Peregrine Adventures
    -8%
    Duration
    13 days
    Price per day
    $258
    From
    $3,658
    US$3,356
    You save: $302
    5 Dec 2020
    10+ spaces left
    23 Jan 2021
    10+ spaces left
    View tour
    More information
  • Cuba Colonial

    "If I was a vegetarian I would have been given more care! I had to get doctors letters..."
    Instant Booking
    Just $99 now
    destinations
    Havana, Santa Clara, Trinidad, Camaguey, Santiago de Cuba, Baracoa+4 more
    starts/ ends in
    Havana / Havana
    age range
    12 to 99 year olds
    accommodation
    Hotel, Home-stay
    transport
    Private Vehicle
    Travel style
    Adventure, Christmas & New Year+1 more
    operator
    G Adventures
    -15%
    Duration
    15 days
    Price per day
    $109
    From
    $1,916
    US$1,629
    Sign up to save $328
    5 Dec 2020
    10+ spaces left
    12 Dec 2020
    10+ spaces left
    View tour
    More information
  • Cuban Rhythms

    "Given the price, this was a good tour. Food in Cuba can be a bit monotonous so be..."
    Instant Booking
    Just $99 now
    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
    Home-stay
    transport
    Boat, Private Vehicle
    Travel style
    Local Living, Christmas & New Year+1 more
    operator
    G Adventures
    -10%
    Duration
    8 days
    Price per day
    $89
    From
    $788
    US$709
    Sign up to save $97
    3 Dec 2020
    10+ spaces left
    6 Dec 2020
    10+ spaces left
    View tour
    More information
  • West Indies Explorer

    11 day ocean cruise tour through San Juan, Tortola, St. Kitts and 6 other destinations in 7 different countries

    Just $99 now
    destinations
    Puerto Rico, Virgin Island, British, Saint Kitts and Nevis, Saint Lucia, Barbados, Dominica, Antigua and Barbuda+6 more
    starts/ ends in
    San Juan / San Juan
    age range
    18 to 90 year olds
    accommodation
    Stateroom / Suite
    Ships
    Viking Sea, Viking Star
    Ocean
    Atlantic
    Travel style
    Beach, Discovery, Christmas & New Year+1 more
    operator
    Viking Cruises
    -21%
    Duration
    11 days
    Price per day
    $293
    From
    $4,100
    US$3,222
    You save: $878
    20 Dec 2020
    10+ spaces left
    30 Dec 2020
    10+ spaces left
    View tour
    More information
  • Cuba on a shoestring

    "Very lucky to have had a fabulous group on this tour. The itinerary was great and..."
    Instant Booking
    Just $99 now
    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
    -24%
    Duration
    8 days
    Price per day
    $89
    From
    $936
    US$712
    You save: $224
    5 Dec 2020
    10+ spaces left
    8 Dec 2020
    10+ spaces left
    View tour
    More information
  • Cuba by Bike

    "Great trip. Well organized. Covered a lot of territory. Nice group. Las knew EVERYTHING,..."
    Just $99 now
    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
    $223
    From
    US$2,679
    You save: $83
    8 Dec 2020
    10+ spaces left
    View tour
    More information
  • Western Cuba

    "We were not met at the airport and could have missed the tour. I found a number and..."
    Instant Booking
    Just $99 now
    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
    -24%
    Duration
    7 days
    Price per day
    $116
    From
    $1,071
    US$814
    You save: $257
    6 Dec 2020
    10+ spaces left
    13 Dec 2020
    10+ spaces left
    View tour
    More information
  • Best of Western Cuba + Beach Extension

    10 day discovery tour through Havana, Vinales, Trinidad, Santa Clara, Jibacoa in Cuba

    Instant Booking
    Just $99 now
    destinations
    Havana, Vinales, Trinidad, Santa Clara, Jibacoa+3 more
    starts/ ends in
    Havana / Havana
    age range
    14 to 85 year olds
    accommodation
    Hotel, Home-stay
    Travel style
    Beach, Coach / Bus, Christmas & New Year+1 more
    operator
    Explore!
    Duration
    10 days
    Price per day
    $150
    From
    US$1,504
    You save: $31
    19 Dec 2020
    10+ spaces left
    26 Dec 2020
    10+ spaces left
    View tour
    More information
  • Cuba Family Holiday

    11 day family tour through Havana, Vinales, Playa Larga, Cienfuegos, Trinidad in Cuba

    Instant Booking
    Just $99 now
    destinations
    Havana, Vinales, Playa Larga, Cienfuegos, Trinidad+3 more
    starts/ ends in
    Havana / Havana
    age range
    5 to 99 year olds
    accommodation
    Hotel, Guesthouse
    transport
    Mini-coach
    Travel style
    Adventure, Discovery, Christmas & New Year+1 more
    operator
    Intrepid Travel
    -24%
    Duration
    11 days
    Price per day
    $113
    From
    $1,641
    US$1,247
    You save: $394
    19 Dec 2020
    10+ spaces left
    27 Dec 2020
    10+ spaces left
    View tour
    More information
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Caribbean Winter Holiday & Vacation Packages Reviews

  • "My husband and I joined Cuban Adventures for the Original Cuba Tour in June/July..."
    Original Cuba - 8 Days
  • "Our guide, Roger (? sp.), was knowledgeable, had a lovely sense of humour, and was..."
    Best of Cuba
  • "A great way to see Cuba in a small group before it gets overtouristed. Our Guide,..."
    Essential Cuba
  • "Guide: David I really liked my trip to Cuba, and I can say the guide makes the difference!..."
    15 Day Original
  • "My trip to Cuba with Jakera turned out to be a life changing experience! I went with..."
    Learn Spanish, Dance & Culture - Cuba 14 Days
  • "Excellent tour would recommend it, but not for everyone, need to be open minded."
    Best of Cuba Westbound