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Sailing Tours/Trips in Caribbean

Sailing Tours/Trips in Caribbean

Find a Sailing trip that explores Caribbean. There are 12 tours to choose from, that range in length from 7 days up to 18 days. The most popular month for these tours is June, which has the most tour departures.

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12 Sailing trips through Caribbean with 25 reviews

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  • Sailing Cuba

    "Exceeded my dreams! Happy highlights include hammock relaxing Turtle release, tropical..."
    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
    -30%
    Duration
    8 days
    Price per day
    $153
    From
    $1,749
    US$1,224
    Sign up to save $574
    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
    -32%
    Duration
    7 days
    Price per day
    $232
    From
    $2,375
    US$1,621
    • +$60 local payments
    You save $754
    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
    $240
    From
    US$2,401
    You save $74
    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
    -25%
    Duration
    8 days
    Price per day
    $164
    From
    $1,749
    US$1,312
    Sign up to save $490
    15 Jun 2019
    10+ spaces left
    13 Jul 2019
    10+ spaces left
    View tour
    More information
  • Cuba Sailing Adventure

    "EXCELLENT ADVENTURE Overall, the sailing trip exceeded expectations in many aspects:..."
    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
    $225
    From
    US$2,027
    You save $52
    27 Apr 2019
    1 space left
    16 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
    $240
    From
    US$2,401
    You save $74
    14 Jun 2019
    6 spaces left
    View tour
    More information
  • Antigua Sailing Week

    9 day sailing tour in Antigua, Antigua and Barbuda

    Instant Booking
    Just $99 deposit
    destinations
    Antigua
    starts/ ends in
    Antigua / Antigua
    age range
    16 to 99 year olds
    accommodation
    Berth / Cabin
    transport
    Ship, Boat
    Ocean
    Atlantic
    operator
    Spartan Ocean Racing
    Duration
    9 days
    Price per day
    $269
    From
    US$2,425
    You save $75
    25 Apr 2019
    10 spaces left
    View tour
    More information
  • The Atlantic Rally of Cruisers - ARC 2019

    18 day sailing tour through Gran Canaria, St.Lucia in 2 different countries

    Instant Booking
    Just $99 deposit
    destinations
    Gran Canaria, St.Lucia+1 more
    starts/ ends in
    Gran Canaria / St.Lucia
    age range
    16 to 99 year olds
    accommodation
    Berth / Cabin
    transport
    Ship, Boat
    Ocean
    Atlantic
    operator
    Spartan Ocean Racing
    Duration
    18 days
    Price per day
    $296
    From
    US$5,335
    You save $165
    22 Nov 2019
    10+ spaces left
    View tour
    More information
  • Sailing the British Virgin Islands – Tortola to Tortola

    "Yes... we knew we were going to have to buy food for meals but the way in which this..."
    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
    $243
    From
    US$1,699
    Sign up to 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
    $240
    From
    US$2,401
    You save $74
    28 Jun 2019
    5 spaces left
    View tour
    More information
  • Easter Cabin Charter Sailing Adventure in the BVI

    10 day sailing tour through Tortola, Spanish Town, Leverick Bay and 6 other destinations in Virgin Island, British

    Instant Booking
    Just $99 deposit
    destinations
    Tortola, Spanish Town, Leverick Bay, Anegada, Cane Garden Bay, Jost van Dyke, Norman Island, Peter Island, Cooper Island+8 more
    starts/ ends in
    Tortola / Tortola
    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
    $240
    From
    US$2,401
    You save $74
    View tour
    More information
  • RORC Caribbean 600 2020

    7 day sailing tour in Nelsons Dockyard, Antigua and Barbuda

    Instant Booking
    Just $99 deposit
    destinations
    Nelsons Dockyard
    starts/ ends in
    Nelsons Dockyard / Nelsons Dockyard
    age range
    16 to 99 year olds
    accommodation
    Berth / Cabin
    transport
    Ship, Boat
    Ocean
    Atlantic
    operator
    Spartan Ocean Racing
    Duration
    7 days
    Price per day
    $346
    From
    US$2,425
    You save $75
    22 Feb 2020
    10+ spaces left
    28 Feb 2020
    10+ spaces left
    View tour
    More information

Sailing 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