BEST SELECTION & PRICESBEST SELECTIONBEST PRICESBOOK FOR $99
Autumn/Fall Tours & Vacation Packages Caribbean

Autumn/Fall Tours & Vacation Packages Caribbean

Searching for tours in Caribbean during Fall / Autumn 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

Unlock up to $350 offMember's Saving - Unlock up to $350in extra savings

50 Caribbean holiday packages in September, October and November

Sort: Popularity
Filters
Sort by
Sort by
  • 15 Day Original

    "My friends and I have done several tours and transfers with Cuban adventures and..."
    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 Sep 2020
    10+ spaces left
    11 Sep 2020
    10+ spaces left
    View tour
    More information
  • Cuban Rhythms

    "Amazing experience! Great tour guide"
    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
    6 Sep 2020
    10+ spaces left
    20 Sep 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
    30 Oct 2020
    10+ spaces left
    9 Nov 2020
    10+ spaces left
    View tour
    More information
  • Cuba Colonial

    "Nadya our CEO was the best!!Always willing to help in anything!Ten +++ for her....."
    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
    26 Sep 2020
    10+ spaces left
    17 Oct 2020
    10+ spaces left
    View tour
    More information
  • Original Cuba - 8 Days

    184 reviews
    AWARD WINNER
    "An excellent tour with an excellent guide! I will be recommending Cuban Adventures!"
    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 Sep 2020
    10+ spaces left
    10 Sep 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
    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
    24 Sep 2020
    10+ spaces left
    8 Oct 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
    10 Oct 2020
    10+ spaces left
    7 Nov 2020
    10+ spaces left
    View tour
    More information
  • Western Cuba

    "5 stars to our tour guide – without a doubt I could not have asked for a better..."
    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 Sep 2020
    10+ spaces left
    20 Sep 2020
    10+ spaces left
    View tour
    More information
  • Essential Cuba

    "We really enjoyed our trip of Cuba and our fellow travellers were great fun."
    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
    19 Sep 2020
    10+ spaces left
    10 Oct 2020
    10+ spaces left
    View tour
    More information
  • Learn Spanish, Dance & Culture - Cuba 14 Days

    "My top on Jakera was profoundly wonderful. The people I met working at Jakera working..."
    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 Sep 2020
    10 spaces left
    20 Sep 2020
    10 spaces left
    View tour
    More information
  • Sailing the British Virgin Islands – Tortola to Tortola

    "I wasn't happy with the self prepared meals we had to buy food for. All the meals..."
    Instant Booking
    Just $99 now
    destinations
    Tortola, Norman Island, Virgin Gorda, Jost van Dyke+3 more
    starts/ ends in
    Tortola / Tortola
    age range
    16 to 99 year olds
    accommodation
    Berth / Cabin
    transport
    Ship
    Ocean
    Atlantic
    Travel style
    Sailboat, Discovery, Christmas & New Year+1 more
    operator
    G Adventures
    -20%
    Duration
    7 days
    Price per day
    $194
    From
    $1,699
    US$1,359
    Sign up to save $374
    11 Oct 2020
    8 spaces left
    18 Oct 2020
    8 spaces left
    View tour
    More information
  • Cuba Explorer

    "Well organised, great mix of organised activities and free time"
    Instant Booking
    Just $99 now
    destinations
    Havana, Santiago de Cuba, Camaguey, Trinidad, Playa Ancon, Santa Clara+5 more
    starts/ ends in
    Havana / Havana
    age range
    15 to 99 year olds
    accommodation
    Guesthouse
    transport
    Private Vehicle
    Country Region
    Central Cuba
    Travel style
    Adventure, Christmas & New Year+1 more
    operator
    Intrepid Travel
    -13%
    Duration
    10 days
    Price per day
    $130
    From
    $1,506
    US$1,303
    You save: $203
    17 Sep 2020
    10+ spaces left
    15 Oct 2020
    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
    Just $99 now
    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!
    Duration
    15 days
    Price per day
    $147
    From
    US$2,205
    You save: $45
    10 Oct 2020
    10+ spaces left
    24 Oct 2020
    10+ spaces left
    View tour
    More information
  • Cycle Cuba: West

    "I had an exceptional trip with intrepid on my recent cycle cuba tour. Our tour guide..."
    Instant Booking
    Just $99 now
    destinations
    Havana, Soroa, Las Terrazas, Vinales, Cayo Juti­as, Consolacion del Sur+4 more
    starts/ ends in
    Havana / Havana
    age range
    15 to 99 year olds
    accommodation
    Guesthouse
    Country Region
    Western Cuba
    Travel style
    Adventure
    operator
    Intrepid Travel
    -37%
    Duration
    7 days
    Price per day
    $121
    From
    $1,331
    US$845
    You save: $486
    14 Sep 2020
    10+ spaces left
    12 Oct 2020
    10+ spaces left
    View tour
    More information
  • Cuba by Bike

    "Very nice scenery and lots of activities. So much fun and I am sure that you'll enjoy..."
    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
    6 Oct 2020
    10+ spaces left
    3 Nov 2020
    10+ spaces left
    View tour
    More information
Load more

Caribbean Autumn/Fall Holiday & Vacation Packages Reviews

  • "Guide: David I really liked my trip to Cuba, and I can say the guide makes the difference!..."
    15 Day Original
  • "By far the best holidays I've ever had. Cuba is beautiful, musical, and addictive!..."
    Cuban Rhythms
  • "Awesome tour!! We had the best CEO, Nadya, such a sweet girl and always willing to..."
    Cuba Colonial
  • "My husband and I joined Cuban Adventures for the Original Cuba Tour in June/July..."
    Original Cuba - 8 Days
  • "Excellent tour would recommend it, but not for everyone, need to be open minded."
    Best of Cuba Westbound
  • "This was the most amazing tour/ holiday i have ever been on. The people were so friendly..."
    Western Cuba