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Sailboat Tours/Trips in Caribbean

Sailboat Tours/Trips in Caribbean

Find a Sailboat trip that explores Caribbean. There are 8 tours to choose from, that range in length from 7 days up to 10 days. The most popular month for these tours is June, 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!

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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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8 Sailboat trips through Caribbean with 25 reviews

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  • Sailing Cuba

    "Great tour, fabulous locations and a great guide. The food was excellent. The boat..."
    Instant Booking
    Just $99 deposit
    destinations
    Havana, Cienfuegos, Cayo Largo, Cayo del Rosario+2 more
    starts/ ends in
    Havana / Havana
    age range
    12 to 99 year olds
    accommodation
    Berth / Cabin
    transport
    Ship
    Travel style
    Sailboat, Discovery, Christmas & New Year+1 more
    operator
    G Adventures
    Duration
    8 days
    Price per day
    $210
    From
    US$1,679
    You save $70
    4 May 2019
    5 spaces left
    18 May 2019
    7 spaces left
    View tour
    More information
  • Bahamas Sailing Adventure

    "Bahamas Sailing - June 2016 - this trip was incredible. 7 days on a Catamaran sailing..."
    Instant Booking
    Just $99 deposit
    destinations
    Marsh Harbour, Tahiti Beach, Hope Town, Man-O-War Cay, Great Guana Cay, Green Turtle Cay+5 more
    starts/ ends in
    Marsh Harbour / Marsh Harbour
    age range
    15 to 99 year olds
    accommodation
    Berth / Cabin
    transport
    Ship
    Regions
    Atlantic, Bahamas
    Travel style
    Sailboat, Discovery
    operator
    Intrepid Travel
    -33%
    Duration
    7 days
    Price per day
    $228
    From
    $2,375
    US$1,596
    • +$60 local payments
    You save $779
    4 May 2019
    2 spaces left
    11 May 2019
    1 space left
    View tour
    More information
  • 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 deposit
    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
    $238
    From
    US$2,376
    You save $99
    31 May 2019
    2 spaces left
    View tour
    More information
  • Sailing Cuba - South Coast Explorer

    8 day sailing tour through Havana, Cienfuegos, Guajimico and 3 other destinations in Cuba

    Instant Booking
    Just $99 deposit
    destinations
    Havana, Cienfuegos, Guajimico, Trinidad, Playa Ancon, Cayos Machos de Fuera+4 more
    starts/ ends in
    Havana / Havana
    age range
    12 to 99 year olds
    transport
    Ship
    Country Region
    Central Cuba
    Travel style
    Sailboat, Discovery
    operator
    G Adventures
    Duration
    8 days
    Price per day
    $210
    From
    US$1,679
    You save $70
    15 Jun 2019
    10+ spaces left
    13 Jul 2019
    10+ spaces left
    View tour
    More information
  • Cuba Sailing Adventure

    "An incredible experience! Small groups of 8 max on a very comfortable 55ft Yacht...."
    Instant Booking
    Just $99 deposit
    destinations
    Havana, Cienfuegos, Cayos de Dios, Cayo Largo+2 more
    starts/ ends in
    Havana / Havana
    age range
    15 to 99 year olds
    accommodation
    Berth / Cabin, Guesthouse
    transport
    Boat, Local Transport
    Travel style
    Adventure, Sailboat, In-depth Cultural+1 more
    operator
    Intrepid Travel
    Duration
    9 days
    Price per day
    $221
    From
    US$1,986
    You save $83
    16 Nov 2019
    6 spaces left
    30 Nov 2019
    6 spaces left
    View tour
    More information
  • Adventure Sailing Trip in Grenada & The Grenadines

    10 day sailing tour through St Georges , Moliniere Point, Carriacou and 8 other destinations in 2 different countries

    Instant Booking
    Just $99 deposit
    destinations
    St Georges , Moliniere Point, Carriacou, Union Island, Petit Saint Vincent, Tobago Cays, Mayreau, Port Elizabeth, Cumberland Bay, Young Island, Saint Vincent+10 more
    starts/ ends in
    St Georges / Saint Vincent
    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
    $238
    From
    US$2,376
    You save $99
    14 Jun 2019
    6 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 deposit
    destinations
    Tortola, Norman Island, Virgin Gorda, Jost van Dyke+3 more
    starts/ ends in
    Tortola / Tortola
    age range
    12 to 99 year olds
    accommodation
    Berth / Cabin
    transport
    Ship
    Ocean
    Atlantic
    Travel style
    Sailboat, Discovery, Christmas & New Year+1 more
    operator
    G Adventures
    Duration
    7 days
    Price per day
    $233
    From
    US$1,631
    You save $68
    13 Oct 2019
    8 spaces left
    20 Oct 2019
    8 spaces left
    View tour
    More information
  • Cabin Charter Sailing Adventure in St Vincent & The Grenadines

    10 day sailing tour through Saint Vincent, Young Island, Cumberland Bay and 8 other destinations in Saint Vincent and the Grenadines

    Instant Booking
    Just $99 deposit
    destinations
    Saint Vincent, Young Island, Cumberland Bay, Petit Nevis, Mustique, Tobago Cays, Mayreau, Mopion Island, Petit Saint Vincent, Union Island, Port Elizabeth+10 more
    starts/ ends in
    Saint Vincent / Saint Vincent
    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
    $238
    From
    US$2,376
    You save $99
    28 Jun 2019
    5 spaces left
    View tour
    More information

Sailboat Tours/Trips in Caribbean Reviews

  • "One of the best, most relaxing weeks of my life sailing in paradise! Amazing beaches,..."
    Sailing Cuba
  • "Bahamas Sailing - June 2016 - this trip was incredible. 7 days on a Catamaran sailing..."
    Bahamas Sailing Adventure
  • "An incredible experience! Small groups of 8 max on a very comfortable 55ft Yacht...."
    Cuba Sailing Adventure
  • "Great to see a fantastic place getting itself back to normality without the crowds."
    Sailing the British Virgin Islands – Tortola to Tortola