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Fall-Autumn 2019 Tours & Vacation Packages Caribbean

Fall-Autumn 2019 Tours & Vacation Packages Caribbean

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

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93 Caribbean vacation packages in October and November

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  • Cuba Colonial

    "Nadya our CEO was the best!!Always willing to help in anything!Ten +++ for her....."
    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
    16 Nov 2019
    1 space left
    30 Nov 2019
    5 spaces left
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    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
    Flexible payments
    destinations
    Havana
    starts/ ends in
    Havana / Havana
    age range
    18 to 99 year olds
    accommodation
    Hostel
    Country Region
    Western Cuba
    Travel style
    Christmas & New Year
    operator
    Bucanero Adventure
    Duration
    14 days
    Price per day
    $57
    From
    US$792
    You save: $15
    3 Nov 2019
    10 spaces left
    17 Nov 2019
    10 spaces left
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    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
    9 Nov 2019
    1 space left
    23 Nov 2019
    8 spaces left
    View tour
    More information
  • Best of Cuba in 10 days

    "The tour for 10 days with MiCuba was very interesting. We saw most of the highlights..."
    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
    27 Oct 2019
    1 space left
    28 Oct 2019
    1 space left
    View tour
    More information
  • Best of Cuba

    "We visited lots of different cities, all different in their own way (a day extra..."
    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
    3 Nov 2019
    6 spaces left
    10 Nov 2019
    6 spaces left
    View tour
    More information
  • Original Cuba - 8 Days

    194 reviews
    AWARD WINNER
    "What an amazing experience we had touring Cuba with your company! We learned so much..."
    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
    31 Oct 2019
    10+ spaces left
    14 Nov 2019
    10 spaces left
    View tour
    More information
  • 15 Day Original

    "very highly recommended, loved it! guide Yaima is tops!"
    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
    1 Nov 2019
    10+ spaces left
    8 Nov 2019
    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
    Flexible payments
    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
    -28%
    Duration
    15 days
    Price per day
    $106
    From
    $2,203
    US$1,588
    You save: $615
    7 Nov 2019
    10+ spaces left
    14 Nov 2019
    10+ spaces left
    View tour
    More information
  • Explore Cuba. Live like a local in 15 days

    "We had a great time in Cuba and really enjoyed our stay in the casas particulares..."
    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
    27 Oct 2019
    2 spaces left
    28 Oct 2019
    2 spaces left
    View tour
    More information
  • Cuban Rhythms: Rum & Fun

    "I once again had a fantastic trip with G and completely fell in love with Cuba! This..."
    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
    19 Nov 2019
    7 spaces left
    21 Nov 2019
    5 spaces left
    View tour
    More information
  • Best of Puerto Rico trip

    "The tour was awesome. Our guide knows very well the road, and when asked and needed..."
    Instant Booking
    Flexible payments
    destinations
    San Juan, Arecibo, Ponce, Fajardo, El Yunque, Carolina+4 more
    starts/ ends in
    San Juan / San Juan
    age range
    8 to 70 year olds
    accommodation
    Hotel
    Travel style
    Family, Christmas & New Year+1 more
    operator
    Spotin
    Duration
    7 days
    Price per day
    $112
    From
    US$784
    You save: $16
    1 Nov 2019
    10+ spaces left
    8 Nov 2019
    10+ spaces left
    View tour
    More information
  • Beautiful Cuba

    "The tour was fantastic, an awesome group helps, but a phenomenal guide certainly..."
    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
    4 Nov 2019
    1 space left
    6 Nov 2019
    6 spaces left
    View tour
    More information
  • Cuba by Bike

    "Jackson was an amazing guide! Learned so much about Cuba past and present. Bikes..."
    Flexible payments
    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
    transport
    Bicycle, Private Vehicle
    Travel style
    Adventure, In-depth Cultural, Historical+2 more
    operator
    World Expeditions
    Duration
    12 days
    Price per day
    $234
    From
    US$2,806
    You save: $28
    5 Nov 2019
    10+ spaces left
    View tour
    More information
  • Sailing Cuba

    "One of the best, most relaxing weeks of my life sailing in paradise! Amazing beaches,..."
    Instant Booking
    Flexible payments
    destinations
    Havana, Cienfuegos, Cayo Largo, Cayo del Rosario+2 more
    starts/ ends in
    Havana / Havana
    age range
    16 to 99 year olds
    accommodation
    Berth / Cabin
    transport
    Ship
    Travel style
    Sailboat, Discovery, Christmas & New Year+1 more
    operator
    G Adventures
    -30%
    Duration
    8 days
    Price per day
    $154
    From
    $1,757
    US$1,230
    Sign up to save $564
    2 Nov 2019
    10+ spaces left
    9 Nov 2019
    5 spaces left
    View tour
    More information
  • Essential Cuba - 8 Days Small Group Tour - Havana, Vinales, Trinidad, Cienfuegos

    "My 8 days in Cuba were extraordinary! As a solo traveler, I could never expect to..."
    Flexible payments
    destinations
    Havana, Trinidad, Cienfuegos, Vinales+2 more
    starts/ ends in
    Havana / Havana
    age range
    20 to 70 year olds
    accommodation
    Home-stay, Guesthouse, Apartment+1 more
    transport
    Coach / Bus, Local Transport, Private Vehicle+2 more
    Travel style
    Local Living
    operator
    VamosCuba
    Duration
    8 days
    Price per day
    $57
    From
    US$459
    • +$278 local payments
    You save: $8
    28 Oct 2019
    10 spaces left
    31 Oct 2019
    10 spaces left
    View tour
    More information
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Caribbean Fall-Autumn 2019 Tours & Vacation Packages Reviews

  • "Awesome tour!! We had the best CEO, Nadya, such a sweet girl and always willing to..."
    Cuba Colonial
  • "My trip to Cuba with Jakera turned out to be a life changing experience! I went with..."
    Learn Spanish, Dance & Culture - Cuba 14 Days
  • "A great way to see Cuba in a small group before it gets overtouristed. Our Guide,..."
    Essential Cuba
  • "It was amazing, great island, great people and the organization was the best! Would..."
    Best of Cuba in 10 days
  • "Our guide, Roger (? sp.), was knowledgeable, had a lovely sense of humour, and was..."
    Best of Cuba
  • "My husband and I joined Cuban Adventures for the Original Cuba Tour in June/July..."
    Original Cuba - 8 Days