BEST SELECTION & PRICESBEST SELECTIONBEST PRICESTRUSTED PAYMENTS
Sort: Popularity
Filters
Sailing Tours/Trips in Caribbean

Sailing Tours/Trips in Caribbean

Find a Sailing trip that explores Caribbean. There are 6 tours to choose from, that range in length from 7 days up to 15 days. The most popular month for these tours is November, which has the most tour departures.

  • Unlock your extra savings
  • 24/7 expert travel advice
  • Personal tour recommendations

Most Wanted Sale

Simply enter your info below and you'll be granted instant access to prices available only to TourRadar members.

ends on 22 Aug 2018
up to
$600
off

By clicking "Unlock Now" you accept our Terms & Conditions

The Most Wanted Sale starts on Friday 17th of August 2018 at 9:00AM in New York EDT and ends on Wednesday 22nd of August 2018 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, Europamundo, Expat Explore, Guide to Iceland, Hiking New Zealand, Monkey Adventures, Oasis Overland, Oku Japan, Peregrine, Stray Asia, Stray Travel, The Dragon Trip, Wilderness Ireland, Wilderness Scotland, Tucan Travel, Avalon Waterways, Cosmos, Globus, Monograms, Contiki, Trafalgar, Insight Vacations, Luxury Gold, U by Uniworld & Uniworld 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.

  • Unlock your extra savings
  • 24/7 expert travel advice
  • Personal tour recommendations
Unlock up to $600 off Most Wanted Sale
ends on 22 Aug 2018

6 Sailing trips through Caribbean with 14 reviews

Sort by
  • Sort by
Create Deal Alert
  • Cuba Libre & Sailing

    "It was just excellence."
    destinations
    Havana, Vinales, Maria La Gorda, San Diego de los Banos, Soroa, Cienfuegos, Cayo Largo, Cayo del Rosario+6 more
    starts/ ends in
    Havana / Havana
    age range
    12 to 70 year olds
    accommodation
    Hotel, Home-stay, Berth / Cabin+1 more
    transport
    Coach / Bus, Ship, Boat, Private Vehicle+1 more
    operator
    G Adventures
    -23%
    Days
    15
    Our saving
    $754
    From
    $3,249
    US $ 2,495
    days
    15
    $166 per day
    29 Sep 2018 3 spaces left
    13 Oct 2018 6 spaces left
    View MoreGetDownload Brochure
  • Sailing the British Virgin Islands – Tortola to Tortola

    "Great to see a fantastic place getting itself back to normality without the crowds."
    destinations
    Tortola, Norman Island, Virgin Gorda, Jost van Dyke+3 more
    starts/ ends in
    Tortola / Tortola
    age range
    12 to 70 year olds
    accommodation
    Berth / Cabin
    transport
    Ship, Boat
    operator
    G Adventures
    -28%
    Days
    7
    Our saving
    $512
    From
    $1,829
    US $ 1,317
    days
    7
    $188 per day
    20 Oct 2018 8 spaces left
    27 Oct 2018 8 spaces left
    View MoreGetDownload Brochure
  • Cuba Sailing Adventure

    "An incredible experience! Small groups of 8 max on a very comfortable 55ft Yacht...."
    destinations
    Havana, Cienfuegos, Cayos de Dios, Cayo Largo+2 more
    starts/ ends in
    Havana / Havana
    age range
    15 to 70 year olds
    accommodation
    Berth / Cabin, Guesthouse
    transport
    Coach / Bus, Boat, Local Transport+1 more
    Travel style
    In-depth Cultural
    operator
    Intrepid Travel
    Days
    9
    Our saving
    $87
    From
    US $ 2,078
    days
    9
    $231 per day
    10 Nov 2018 5 spaces left
    17 Nov 2018 7 spaces left
    View MoreGetDownload Brochure
  • Bahamas Sailing Adventure

    "Bahamas Sailing - June 2016 - this trip was incredible. 7 days on a Catamaran sailing..."
    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
    Islands
    Bahamas
    operator
    Intrepid Travel
    Days
    7
    Our saving
    $88
    From
    US $ 2,112
    days
    7
    $302 per day
    23 Mar 2019 8 spaces left
    30 Mar 2019 8 spaces left
    View MoreGetDownload Brochure
  • Sailing Cuba

    "Relaxing tour with the best skipper and tour leader (CEO) anyone could ask for!"
    destinations
    Havana, Cienfuegos, Cayo Largo, Cayo del Rosario+2 more
    starts/ ends in
    Havana / Havana
    age range
    12 to 70 year olds
    accommodation
    Berth / Cabin
    transport
    Ship, Boat
    operator
    G Adventures
    -23%
    Days
    8
    Our saving
    $487
    From
    $2,099
    US $ 1,612
    days
    8
    $202 per day
    25 Aug 2018 8 spaces left
    6 Oct 2018 7 spaces left
    View MoreGetDownload Brochure
  • Sailing Cuba - South Coast Explorer

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

    destinations
    Havana, Cienfuegos, Guajimico, Trinidad, Playa Ancon, Cayos Machos de Fuera+4 more
    starts/ ends in
    Havana / Havana
    age range
    12 to 70 year olds
    transport
    Ship
    Country Region
    Central Cuba
    operator
    G Adventures
    -33%
    Days
    8
    Our saving
    $688
    From
    $2,099
    US $ 1,410
    days
    8
    $176 per day
    3 Nov 2018 10+ spaces left
    15 Dec 2018 10+ spaces left
    View MoreGetDownload Brochure

Sailing Tours/Trips in Caribbean Reviews

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