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Caribbean Tours for Seniors

Caribbean Tours for Seniors

Say yes to the trip of a lifetime and go touring through Caribbean alongside other adventurers aged 50 and over! These incredible itineraries will take you through iconic destinations like Havana, Trinidad, and wherever else you've been dreaming of. After all, it's never too late to explore the world.

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99 trips for 'over 50s' in Caribbean with 328 reviews

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  • Best of Cuba

    "Tony Mas is the best guide I have ever had in my years of travellilng. He was very..."
    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
    $2,060
    US$1,453
    You save: $607
    28 Jul 2019
    9 spaces left
    4 Aug 2019
    10+ spaces left
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    More information
  • Vivacious Cuba Group Tour - 10 Days

    "Fantastic value! Comfortable accommodations. Great food. Our guide was enthusiastic..."
    Instant Booking
    Just $99 now
    destinations
    Havana, Cienaga de Zapata NP, Cienfuegos, Santa Clara, Trinidad, Vinales+5 more
    starts/ ends in
    Havana / Havana
    age range
    15 to 70 year olds
    accommodation
    Home-stay, Guesthouse
    transport
    Private Vehicle
    Country Region
    Cuba for US Citizens
    Travel style
    Christmas & New Year
    operator
    Locally Sourced Cuba Tours
    Duration
    10 days
    Price per day
    $82
    From
    US$823
    You save: $25
    4 Aug 2019
    8 spaces left
    11 Aug 2019
    8 spaces left
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  • Cuba Group Tour - 8 Days

    "We loved our time in Cuba and really appreciated Manolo showing us his country through..."
    Instant Booking
    Just $99 now
    destinations
    Havana, Cienaga de Zapata NP, Cienfuegos, Santa Clara, Trinidad, Vinales+5 more
    starts/ ends in
    Havana / Havana
    age range
    15 to 70 year olds
    accommodation
    Home-stay, Guesthouse
    transport
    Private Vehicle
    Country Region
    Cuba for US Citizens
    Travel style
    Christmas & New Year
    operator
    Locally Sourced Cuba Tours
    Duration
    8 days
    Price per day
    $85
    From
    US$681
    You save: $21
    4 Aug 2019
    10 spaces left
    11 Aug 2019
    8 spaces left
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    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
    $108
    From
    $1,908
    US$1,622
    Sign up to save $327
    31 Aug 2019
    10 spaces left
    21 Sep 2019
    10 spaces left
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    More information
  • Beautiful Cuba

    "Amazing and fantastic tour. The people are sooo proud of their country even tho it..."
    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
    Guesthouse
    transport
    Private Vehicle
    Travel style
    Christmas & New Year
    operator
    Intrepid Travel
    -13%
    Duration
    8 days
    Price per day
    $177
    From
    $1,634
    US$1,417
    You save: $217
    3 Aug 2019
    3 spaces left
    14 Aug 2019
    2 spaces left
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  • Sailing Cuba

    "Great tour, fabulous locations and a great guide. The food was excellent. The boat..."
    Instant Booking
    Just $99 now
    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
    -25%
    Duration
    8 days
    Price per day
    $158
    From
    $1,683
    US$1,262
    Sign up to save $452
    3 Aug 2019
    8 spaces left
    10 Aug 2019
    3 spaces left
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  • Essential Cuba

    "A great way to see Cuba in a small group before it gets overtouristed. Our Guide,..."
    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
    27 Jul 2019
    6 spaces left
    10 Aug 2019
    7 spaces left
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  • Taste of the Caribbean 13 Days (9 destinations)

    13 day discovery tour through Nassau, Long Island, Mayaguana and 6 other destinations in 3 different countries

    Just $99 now
    destinations
    Bahamas, Jamaica, Cuba+1 more
    starts/ ends in
    Nassau / Havana
    age range
    12 to 99 year olds
    accommodation
    Guesthouse, Hut
    Ship
    Scenic Eclipse
    Travel style
    Ocean Cruise
    operator
    Scenic Luxury Cruises & Tours
    Duration
    13 days
    Price per day
    $709
    From
    US$9,217
    You save: $285
    8 Oct 2019
    10 spaces left
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  • Adventure Sailing Charter from St Lucia to Grenada

    10 day sailing tour through Rodney Bay, Marigot Bay, Soufriere and 10 other destinations in 3 different countries

    Instant Booking
    Just $99 now
    destinations
    Saint Lucia, Saint Vincent and the Grenadines, Grenada+2 more
    starts/ ends in
    Rodney Bay / St Georges
    age range
    30 to 65 year olds
    accommodation
    Berth / Cabin
    transport
    Boat
    Ocean
    Atlantic
    Travel style
    Sailboat
    operator
    BlueFoot Travel
    Duration
    10 days
    Price per day
    $264
    From
    US$2,643
    You save: $82
    22 Nov 2019
    5 spaces left
    29 May 2020
    6 spaces left
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    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
    Just $99 now
    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
    Country Region
    Cuba for US Citizens
    Travel style
    Local Living, Christmas & New Year+1 more
    operator
    MiCuba
    -15%
    Duration
    10 days
    Price per day
    $64
    From
    $745
    US$636
    You save: $109
    24 Jul 2019
    1 space left
    25 Jul 2019
    1 space left
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  • 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
    12 Oct 2019
    5 spaces left
    23 Nov 2019
    10+ spaces left
    View tour
    More information
  • Explore Cuba. Live like a local in 15 days

    "Tourradar took away all the stress that comes with travelling. We could really sit..."
    Instant Booking
    Just $99 now
    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
    Country Region
    Cuba for US Citizens
    Travel style
    Local Living, In-depth Cultural, Christmas & New Year+2 more
    operator
    MiCuba
    -15%
    Duration
    15 days
    Price per day
    $62
    From
    $1,083
    US$924
    You save: $159
    24 Jul 2019
    1 space left
    25 Jul 2019
    1 space 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
    $146
    From
    US$2,194
    You save: $45
    12 Oct 2019
    10+ spaces left
    23 Nov 2019
    9 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$1,497
    You save: $31
    19 Oct 2019
    9 spaces left
    16 Nov 2019
    3 spaces left
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    More information
  • Discover Cuba - 15 days

    15 day in-depth cultural tour through Havana, Vinales, Cienfuegos and 9 other destinations in Cuba

    Just $99 now
    destinations
    Havana, Vinales, Cienfuegos, Trinidad, Parque Natural El Cubano, Camaguey, Bayamo, Sierra Maestra NP, Santiago de Cuba, Baracoa, Parque Nacional Alejandro de Humboldt, Guardalavaca+10 more
    starts/ ends in
    Havana / Guardalavaca
    age range
    18 to 70 year olds
    Travel style
    Discovery
    operator
    On The Go Tours
    Duration
    15 days
    Price per day
    $202
    From
    US$3,024
    Sign up to save $76
    26 Aug 2019
    4 spaces left
    View tour
    More information
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Caribbean Tours for Seniors Reviews

  • "Our guide, Roger (? sp.), was knowledgeable, had a lovely sense of humour, and was..."
    Best of Cuba
  • "A great way to see Cuba, loved staying in Casas, the perfect way to get the real..."
    Vivacious Cuba Group Tour - 10 Days
  • "Our tour gave us a feel for Cuba which I don't think that we would have got on our..."
    Cuba Group Tour - 8 Days
  • "Awesome tour!! We had the best CEO, Nadya, such a sweet girl and always willing to..."
    Cuba Colonial
  • "Amazing and fantastic tour. The people are sooo proud of their country even tho it..."
    Beautiful Cuba
  • "One of the best, most relaxing weeks of my life sailing in paradise! Amazing beaches,..."
    Sailing Cuba