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Historical Tours/Trips in Caribbean

Historical Tours/Trips in Caribbean

Find a Historical trip that explores Caribbean. There are 10 tours to choose from, that range in length from 5 days up to 15 days. The most popular month for these tours is November, which has the most tour departures.

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Easter Sale

We've teamed up with the Easter Bunny himself to find the very best treats this year: big savings on some of our best tours!

ends on 24 Apr 2019
up to
$600
off

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Terms & Conditions

The Easter Sale starts on Friday 19th of April 2019 at 9:00AM in Brisbane AEST and ends on Wednesday 24th of April 2019 at 11:59PM in San Francisco PDT. Unlock this saving with your personal email address and full name. Once unlocked, the saving will be applied automatically to all applicable tour listings and your booking upon check-out. All tours from AmaWaterways, Butterfield & Robinson, Cuban Adventures, Custom Walks, Dragoman, Europamundo, Guide to Iceland, Hiking New Zealand, Monkey Adventures, Oasis Overland, Oku Japan, Red Cat Adventures, SpiceRoads Cycling, Stray Asia, Stray Travel, Sunway Safaris, Wilderness Ireland, Wilderness Scotland, and Tucan Travel are excluded from this extra discounted offer. Moreover, bookings made in USD or CAD for tours operated by Cosmos, Globus and Monograms, as well as tours booked in GBP operated by Travel Talk and The Dragon Trip, tours booked in USD operated by Contiki, Trafalgar, Insight Vacations, Luxury Gold, U by Uniworld & Uniworld, tours booked in NZD and EUR operated by Collette and tours booked in AUD, GBP, EUR and NZD operated by Intrepid, Geckos and Peregrine are excluded from this discounted offer. Current sale pricing, promotional codes and other special offers cannot be applied toward prior purchases. Discounts can be applied on top of participating Operators discounts, but cannot be combined with any existing TourRadar discounts (Friends with Benefits, Traveller's Credits, other TourRadar Promo codes). Refunds on item(s) purchased during a sale will be calculated based on the total basket value of the item(s) kept and any discount associated with the revised total amount. TourRadar reserves the right to terminate the advertised sale without notice. For full terms and conditions, please see here.

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Unlock up to $600 off Easter Sale Unlock up to $600 in extra savings
ends on 24 Apr 2019

10 Historical trips through Caribbean with 23 reviews

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  • One Week in Cuba

    "We had Yenni as our guide, who was completely passionate, knew all the right places..."
    Instant Booking
    Just $99 deposit
    destinations
    Havana, Santa Clara, Trinidad, Vinales+2 more
    starts/ ends in
    Havana / Havana
    age range
    18 to 29 year olds
    accommodation
    Guesthouse
    transport
    Private Vehicle
    Travel style
    Historical, Christmas & New Year+1 more
    operator
    Intrepid Travel
    -26%
    Duration
    8 days
    Price per day
    $82
    From
    $888
    US$658
    You save $230
    7 May 2019
    6 spaces left
    21 May 2019
    10+ spaces left
    View tour
    More information
  • Trinidad Eco-Cultural Experience 5D/4N

    5 day sightseeing tour through Port of Spain, San Fernando in Trinidad and Tobago

    Instant Booking
    Just $99 deposit
    destinations
    Port of Spain, San Fernando+1 more
    starts/ ends in
    Port of Spain / San Fernando
    age range
    3 to 85 year olds
    accommodation
    Hotel
    transport
    Coach / Bus, Private Vehicle+1 more
    Travel style
    Beach, Wildlife, Historical+1 more
    operator
    Island Experiences
    Duration
    5 days
    Price per day
    $165
    From
    US$826
    You save $34
    23 Apr 2019
    8 spaces left
    2 May 2019
    8 spaces left
    View tour
    More information
  • Rediscover Cuba A Cultural Exploration (Santa Clara to Havana) (2019)

    8 day in-depth cultural tour through Santa Clara, Cayo Santa Maria, San Juan de los Remedios, Cienfuegos, Havana in Cuba

    Just $99 deposit
    destinations
    Santa Clara, Cayo Santa Maria, San Juan de los Remedios, Cienfuegos, Havana+4 more
    starts/ ends in
    Santa Clara / Havana
    age range
    5 to 99 year olds
    accommodation
    Hotel
    transport
    Plane
    Country Region
    Central Cuba
    Travel style
    Historical
    operator
    Collette
    Duration
    8 days
    Price per day
    $360
    From
    US$2,879
    You save $120
    3 Sep 2019
    7 spaces left
    22 Oct 2019
    8 spaces left
    View tour
    More information
  • Central Cuba

    9 day bicycle tour through Havana, Playa Larga, Playa Giron, Cienfuegos, Trinidad in Cuba

    Instant Booking
    Just $99 deposit
    destinations
    Havana, Playa Larga, Playa Giron, Cienfuegos, Trinidad+3 more
    starts/ ends in
    Havana / Havana
    age range
    12 to 80 year olds
    accommodation
    Guesthouse
    transport
    Bicycle, Mini-coach
    Travel style
    Local Living, Discovery, Historical+1 more
    operator
    Cubyke
    Duration
    9 days
    Price per day
    $233
    From
    US$2,096
    You save $87
    29 Apr 2019
    10+ spaces left
    3 Jun 2019
    10+ spaces left
    View tour
    More information
  • Cuba 2019 with York College of Pennsylvania

    14 day in-depth cultural tour through Havana, Sancti Spiritus, Bayamo and 5 other destinations in Cuba

    Just $99 deposit
    destinations
    Havana, Sancti Spiritus, Bayamo, Santiago de Cuba, Camaguey, Trinidad, Cienfuegos, Vinales+7 more
    starts/ ends in
    Havana / Havana
    age range
    40 to 80 year olds
    accommodation
    Hotel
    transport
    Coach / Bus
    Travel style
    Historical
    operator
    Adventures Abroad
    Duration
    14 days
    Price per day
    $205
    From
    US$2,875
    You save $120
    3 Jun 2019
    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 deposit
    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
    8 Oct 2019
    10+ spaces left
    5 Nov 2019
    10+ spaces left
    View tour
    More information
  • Western Cuba

    "Just got back from 9-day tour of Cuba with Globe Drifters. Trip of a lifetime. Our..."
    Just $99 deposit
    destinations
    Havana, Vinales, Playa Larga, Trinidad+2 more
    starts/ ends in
    Havana / Havana
    age range
    18 to 99 year olds
    accommodation
    Home-stay, Guesthouse
    transport
    Coach / Bus, Local Transport, Private Vehicle, Mini-coach+3 more
    Country Region
    Cuba for US Citizens
    Travel style
    Historical
    operator
    Globe Drifters
    Duration
    9 days
    Price per day
    $277
    From
    US$2,496
    You save $104
    9 Nov 2019
    10+ spaces left
    View tour
    More information
  • Cuba – Rum and Revolution

    10 day in-depth cultural tour through Havana, Santa Clara, Trinidad and 5 other destinations in Cuba

    Just $99 deposit
    destinations
    Havana, Santa Clara, Trinidad, Cienfuegos, Playa Giron, Cienaga de Zapata NP, Las Terrazas, Vinales+6 more
    starts/ ends in
    Havana / Havana
    age range
    18 to 99 year olds
    accommodation
    Home-stay, Guesthouse
    Travel style
    Adventure, Coach / Bus, Historical+1 more
    operator
    Diesel Adventures
    Duration
    10 days
    Price per day
    $192
    From
    US$1,915
    You save $80
    14 Nov 2019
    10+ spaces left
    View tour
    More information
  • Cuba a Cultural, Historical, Interpersonal Adventure

    15 day in-depth cultural tour through Havana, Vinales, Cienfuegos and 7 other destinations in Cuba

    Just $99 deposit
    destinations
    Havana, Vinales, Cienfuegos, Sancti Spiritus, Camaguey, Santiago de Cuba, Bayamo, Trinidad, Topes de Collantes, Santa Clara+8 more
    starts/ ends in
    Havana / Havana
    age range
    40 to 80 year olds
    accommodation
    Hotel
    transport
    Coach / Bus
    Travel style
    Historical
    operator
    Adventures Abroad
    Duration
    15 days
    Price per day
    $242
    From
    US$3,629
    You save $151
    4 Nov 2019
    10+ spaces left
    20 Jan 2020
    10 spaces left
    View tour
    More information
  • Cuba: Best of Cuba - Licensed & Approved for US Citizen Group Travel - 9 Days (from Miami to Cienfuegos)

    9 day discovery tour through Miami, Havana, Trinidad, Cienfuegos in 2 different countries

    Just $99 deposit
    destinations
    Miami, Havana, Trinidad, Cienfuegos+2 more
    starts/ ends in
    Miami / Cienfuegos
    age range
    10 to 80 year olds
    Travel style
    Local Living, In-depth Cultural, Historical+2 more
    operator
    GECtravel
    Duration
    9 days
    Price per day
    $288
    From
    US$2,591
    You save $108
    7 Dec 2019
    10+ spaces left
    View tour
    More information

Historical Tours/Trips in Caribbean Reviews

  • "Cuba was such a great, untouched destination, made very accessible by our local guide..."
    One Week in Cuba
  • "Jackson was an amazing guide! Learned so much about Cuba past and present. Bikes..."
    Cuba by Bike
  • "I went to Cuba with Globe Drifters earlier this year and had an experience of a lifetime!..."
    Western Cuba