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Winter 2019 Tours & Vacation Packages Caribbean

Winter 2019 Tours & Vacation Packages Caribbean

Searching for tours in Caribbean during Winter 2019? Look no further, as our tours of Caribbean will allow you to discover exceptional destinations such as Cuba and Jamaica. Taste the adventure and discover new cultures

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111 Caribbean vacation packages in December, January and February

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  • Best of Cuba

    "This was my first tour with Intrepid but I have previously only ever heard good things..."
    Instant Booking
    Flexible payments
    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
    -17%
    Duration
    15 days
    Price per day
    $122
    From
    $2,192
    US$1,823
    You save: $369
    8 Dec 2019
    8 spaces left
    15 Dec 2019
    3 spaces left
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    More information
  • Explore Cuba. Live like a local in 15 days

    "I can only say one thing: WOW ! It was my fourth time in Cuba (each year with a different..."
    Instant Booking
    Flexible payments
    destinations
    Havana, Vinales, Cienfuegos, Santa Clara, Sancti Spiritus, Trinidad, Varadero+5 more
    starts/ ends in
    Havana / Havana
    age range
    15 to 99 year olds
    accommodation
    Home-stay, Guesthouse
    transport
    Coach / Bus, Local Transport, Private Vehicle, Mini-coach+3 more
    Travel style
    Local Living, In-depth Cultural, Christmas & New Year+2 more
    operator
    MiCuba
    Duration
    15 days
    Price per day
    $70
    From
    US$1,047
    You save: $21
    1 Dec 2019
    4 spaces left
    2 Dec 2019
    4 spaces left
    View tour
    More information
  • Cuban Rhythms: Rum & Fun

    "Amazing experience! Great tour guide"
    Instant Booking
    Flexible payments
    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
    -15%
    Duration
    8 days
    Price per day
    $89
    From
    $833
    US$708
    Sign up to save $146
    8 Dec 2019
    9 spaces left
    10 Dec 2019
    8 spaces left
    View tour
    More information
  • Original Cuba - 8 Days

    194 reviews
    AWARD WINNER
    "Everything was wonderful. However, as an American I was made uncomfortable by the..."
    Instant Booking
    Flexible payments
    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
    Travel style
    Local Living, Christmas & New Year+1 more
    operator
    Cuban Adventures
    Duration
    8 days
    Price per day
    $52
    From
    US$414
    • +$200 local payments
    You save: $8
    5 Dec 2019
    5 spaces left
    12 Dec 2019
    10+ spaces left
    View tour
    More information
  • 15 Day Original

    "This was an experience of a lifetime. Was lucky to have Monica as our tour guide...."
    Flexible payments
    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
    $58
    From
    US$868
    • +$250 local payments
    You save: $16
    20 Dec 2019
    10 spaces left
    27 Dec 2019
    6 spaces left
    View tour
    More information
  • Cuba Highlights

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

    Instant Booking
    Flexible payments
    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
    -18%
    Duration
    14 days
    Price per day
    $207
    From
    $3,544
    US$2,898
    You save: $646
    28 Dec 2019
    7 spaces left
    25 Jan 2020
    8 spaces left
    View tour
    More information
  • Essential Cuba

    "A great way to see Cuba in a small group before it gets overtouristed. Our Guide,..."
    Instant Booking
    Flexible payments
    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
    -24%
    Duration
    9 days
    Price per day
    $214
    From
    $2,547
    US$1,928
    You save: $619
    28 Dec 2019
    3 spaces left
    4 Jan 2020
    1 space left
    View tour
    More information
  • Best of Cuba in 10 days

    "I went to Cuba with my family. The whole tour was very good organized. I can't complain...."
    Instant Booking
    Flexible payments
    destinations
    Havana, Trinidad, Varadero+1 more
    starts/ ends in
    Havana / Havana
    age range
    15 to 99 year olds
    accommodation
    Home-stay, Guesthouse
    transport
    Coach / Bus, Bicycle, Private Vehicle, Mini-coach+2 more
    Travel style
    Local Living, Christmas & New Year+1 more
    operator
    MiCuba
    Duration
    10 days
    Price per day
    $72
    From
    US$720
    You save: $15
    1 Dec 2019
    1 space left
    2 Dec 2019
    1 space left
    View tour
    More information
  • Beautiful Cuba

    "Amazing and fantastic tour. The people are sooo proud of their country even tho it..."
    Instant Booking
    Flexible payments
    destinations
    Havana, Soroa, Vinales, Trinidad, Cienfuegos+3 more
    starts/ ends in
    Havana / Havana
    age range
    15 to 99 year olds
    accommodation
    Guesthouse
    transport
    Private Vehicle
    Travel style
    Christmas & New Year
    operator
    Intrepid Travel
    -17%
    Duration
    8 days
    Price per day
    $182
    From
    $1,747
    US$1,454
    You save: $293
    7 Dec 2019
    5 spaces left
    11 Dec 2019
    8 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
    Flexible payments
    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
    $112
    From
    $1,979
    US$1,682
    Sign up to save $347
    14 Dec 2019
    9 spaces left
    23 Dec 2019
    10+ spaces left
    View tour
    More information
  • Cuba Libre!

    15 day discovery tour through Havana, Vinales, Santa Clara and 9 other destinations in Cuba

    Instant Booking
    Flexible payments
    destinations
    Havana, Vinales, Santa Clara, Sancti Spiritus, Camaguey, Bayamo, Santiago de Cuba, Playa Santa Lucia, Trinidad, Topes de Collantes, Cienfuegos, Playa Giron+10 more
    starts/ ends in
    Havana / Havana
    age range
    14 to 85 year olds
    accommodation
    Hotel, Camping
    transport
    Coach / Bus
    Travel style
    Adventure, Sightseeing, In-depth Cultural+1 more
    operator
    Explore!
    -5%
    Duration
    15 days
    Price per day
    $142
    From
    $2,249
    US$2,136
    You save: $112
    21 Dec 2019
    10 spaces left
    25 Jan 2020
    10+ spaces left
    View tour
    More information
  • Cuba Explorer

    "The itinerary of this tour includes the best destinations possible to cover within..."
    Instant Booking
    Flexible payments
    destinations
    Havana, Vinales, Santa Clara, Trinidad+2 more
    starts/ ends in
    Havana / Havana
    age range
    12 to 99 year olds
    accommodation
    Home-stay
    transport
    Private Vehicle
    Travel style
    Adventure, Christmas & New Year+1 more
    operator
    G Adventures
    -15%
    Duration
    9 days
    Price per day
    $134
    From
    $1,423
    US$1,209
    Sign up to save $250
    1 Dec 2019
    5 spaces left
    8 Dec 2019
    7 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
    Flexible payments
    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!
    -5%
    Duration
    10 days
    Price per day
    $148
    From
    $1,556
    US$1,478
    You save: $78
    23 Dec 2019
    10+ spaces left
    18 Jan 2020
    10+ spaces left
    View tour
    More information
  • Learn Spanish, Dance & Culture - Cuba 28 days

    "I had a brilliant experience in Cuba. Everyone involved could nit of been more helpful..."
    Instant Booking
    Flexible payments
    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
    Travel style
    In-depth Cultural, Christmas & New Year+1 more
    operator
    Bucanero Adventure
    Duration
    28 days
    Price per day
    $55
    From
    US$1,552
    You save: $28
    1 Dec 2019
    10 spaces left
    15 Dec 2019
    10 spaces left
    View tour
    More information
  • Western Cuba

    "This was the most amazing tour/ holiday i have ever been on. The people were so friendly..."
    Instant Booking
    Flexible payments
    destinations
    Havana, Las Terrazas, Soroa, Vinales+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
    -28%
    Duration
    7 days
    Price per day
    $117
    From
    $1,140
    US$821
    You save: $319
    8 Dec 2019
    10 spaces left
    15 Dec 2019
    9 spaces left
    View tour
    More information
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Caribbean Winter 2019 Tours & Vacation Packages Reviews

  • "Our guide, Roger (? sp.), was knowledgeable, had a lovely sense of humour, and was..."
    Best of Cuba
  • "We had a wonderful time in Cuba on our family holiday. Maayke helped us organize..."
    Explore Cuba. Live like a local in 15 days
  • "By far the best holidays I've ever had. Cuba is beautiful, musical, and addictive!..."
    Cuban Rhythms: Rum & Fun
  • "My husband and I joined Cuban Adventures for the Original Cuba Tour in June/July..."
    Original Cuba - 8 Days
  • "Guide: David I really liked my trip to Cuba, and I can say the guide makes the difference!..."
    15 Day Original
  • "A great way to see Cuba in a small group before it gets overtouristed. Our Guide,..."
    Essential Cuba