Caribbean and Cuba Sailing Cruises

Cruise Collection

Caribbean and Cuba

All of our Star Clippers Carribean and Cuba cruises are shown below. Tick the boxes to filter by date, ship and duration.

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  • Grenadine Islands

    7 Nights - Barbados and back

    Star Clippers Ship - Royal Clipper Royal Clipper

    Explore the spice island of Grenada and uninhabited Tobago Cays on this sailing voyage to the Grenadine Islands on superb tall ship Royal Clipper 2017 - Dec
    2018 - Jan, Feb, Mar, Dec
    2019 - Jan, Feb, Mar
    Save up to 20% on Winter 2018/19 PLUS exclusive £50pp on all dates!

    Grenadine Islands Cruise on Royal Clipper Cruise Only
    From £1070pp
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  • Windward Islands

    7 Nights - Barbados and back

    Star Clippers Ship - Royal Clipper Royal Clipper

    Explore the idyllic Windward Islands on this sailing voyage on magnificent tall ship Royal Clipper visiting picturesque St Lucia, historic Antigua and the chic capital of Martinique 2017 - Dec
    2018 - Jan, Feb, Mar, Dec
    2019 - Jan, Feb, Mar
    Save up to 20% on Winter 2018/19 PLUS exclusive £50pp on all dates!

    Caribbean Windward Islands Sailing Cruise on Royal Clipper from Barbados Cruise Only
    From £1070pp
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  • Treasure Islands

    7 Nights - St Maarten and back

    Star Clippers Ship - Star Flyer Star Flyer

    A fascinating sailing holiday from St Maarten to the unspoilt British Virgin Islands including stunning beaches at Virgin Gorda and Jost Van Dyke, plus rainforested St Kitts and glamorous St Barts 2018 - Feb, Mar, Dec
    2019 - Jan, Feb, Mar
    Save 10% on Winter 2018/19 PLUS exclusive £50pp discount on all dates!

    Treasure Islands Cruise Only
    From £1079pp
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  • Leeward Islands Sailing Cruise

    7 Nights - St Maarten and back

    Star Clippers Ship - Star Flyer Star Flyer

    Explore the exotic Iles des Saintes, sophisticated St Barts and colonial Antigua on this relaxing Leeward Islands sailing holiday from St Maarten 2018 - Feb, Mar, Dec
    2019 - Jan, Feb, Mar
    Save 10% on Winter 2018/19 PLUS exclusive £50pp discount on all dates!

    Leeward Islands Tall Ship Sailing Cruise Cruise Only
    From £1079pp
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  • Westbound Transatlantic Sailing

    16 Nights - Europe to Caribbean

    Star Clippers Ship - Royal Clipper Choice of Ships

    Re-live the romantic age of sail on one of these Westbound Transatlantic sailing crossings departing from Las Palmas or Lisbon to the Caribbean aboard Royal Clipper or Star Flyer 2017 - Nov
    2018 - Oct, Nov
    Save 20% on 2018 PLUS exclusive £50pp discount on all dates!

    Westbound Transatlantic Sailing Cruise Only
    From £1126pp
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  • Eastbound Transatlantic

    16 Nights - Caribbean to Europe

    Star Clippers Ship - Royal Clipper Choice of Ships

    Enjoy the sailing adventure of a lifetime on one of these superb Eastbound transatlantic sailings departing from Barbados or St Maarten on tall ships Royal Clipper or Star Flyer 2018 - Mar, Apr
    Save 20% PLUS exclusive £50pp discount!

    Eastbound Transatlantic Cruise Only
    From £1142pp
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  • Cuba and Cayman Islands Discovery

    9 Nights - Havana to Cienfuegos

    Star Clippers Ship - Star Flyer Star Flyer

    Enjoy overnight stops in the lively cities of Havana and Cienfuegos, and explore the sun-kissed Cayman Islands, on this relaxing voyage under full sail on tall ship Star Flyer 2017 - Dec
    2018 - Jan
    600 Euro OBC per couple or no single supplement on 18 Dec 2017!

    Cuba and Cayman Islands Discovery Cruise Only
    From £1655pp
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  • Caribbean Crossing

    11 Nights - Montego Bay to Bridgetown

    Star Clippers Ship - Royal Clipper Royal Clipper

    Sail from Jamaica to Barbados on board magnificent tall ship Royal Clipper and visit stunning Caribbean islands including historic Antigua, glamorous St Barts and picturesque St Lucia 2018 - Dec
    Save 20% PLUS exclusive £50pp discount!

    Caribbean Crossing Cruise Only
    From £1842pp
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  • Panama Canal to the Caribbean

    14 Nights - Balboa to St Maarten

    Star Clippers Ship - Star Flyer Star Flyer

    This 14-night tall ship sailing holiday includes a transit of the magnificent Panama Canal, visits the historic town of Cartagena and explores the stunning islands of the Caribbean 2018 - Dec
    Save 10% PLUS exclusive £50pp discount!

    Panama Canal to the Caribbean Cruise Only
    From £2398pp
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  • Barbados and Panama

    14 Nights - Barbados to Balboa

    Star Clippers Ship - Star Flyer Choice of Ships

    A sailing holiday from Barbados with a transit of the magnificent Panama Canal visiting the Grenadines, the World Heritage Site of Cartagena and the remote San Blas islands 2017 - Nov
    2018 - Nov
    Save 10% on 2018 PLUS exclusive £50pp discount on all dates!

    Barbados and Panama Cruise Only
    From £2398pp
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  • ABC Islands and Grenadines

    14 Nights - Barbados and back

    Star Clippers Ship - Royal Clipper Royal Clipper

    Join Royal Clipper on this relaxing voyage under full sail visiting the beautiful islands scattered off the coast of Venezuela, the idyllic ABC Islands of Aruba, Bonaire and Curacao and the picture-postcard Grenadines 2018 - Mar, Apr
    Exclusive £50pp discount!

    ABC Islands and Grenadines Cruise Only
    From £2820pp
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