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Caribbean
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    • Caribbean

    Candy-colored cocktails sipped in seaside watering holes. Carefree days followed by calypso-flavored nights. These are the siren songs that lure anyone with a yacht and a yearning to escape to the incomparable Caribbean Islands. Whether you’re sailing through turquoise waters, lazing on powdery white beaches, the glamorous harbors and unknown coves of this area remain a hidden treasure.

    While Cuba has been off-limits to most American travelers since 1963, in recent years cruise ships have started calling again and flights from the United States have resumed. Most visitors today are drawn not only by the island’s mild climate and beautiful beaches but also its cultural riches. Havana has a wealth of colonial buildings and vintage automobiles, as well as intimate paladares that serve local dishes and street parties that move to the rhythms of mambo and salsa. On the country's southern coast, Cienfuegos has elegant mansions and a 19th-century street plan that earned it a place on UNESCO’s list of World Heritage sites.
    Explore Caribbean
    Candy-colored cocktails sipped in seaside watering holes. Carefree days followed by calypso-flavored nights. These ..read more
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    7 Days - Windward Ways & Tobago Cays [Bridgetown to Oranjestad]

    7 Days - Windward Ways & Tobago Cays [Bridgetown to Oranjestad]
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    Starting from $1,799*

    Cruise Line: Windstar Cruise

    Ship:  Star Breeze / Star Legend

    Sailing Dates:  Jan 21 2023 | Feb 18 2023

    Port: Bridgetown to Oranjestad

    ( Note: Optional tours are available from most ports for an additional charge. )

    7 Days - Windward Ways & Tobago Cays [Bridgetown to Oranjestad]
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    14 days - Star Collector: Lovely Leewards [San Juan to San Juan]

    14 days - Star Collector: Lovely Leewards [San Juan to San Juan]
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    Starting from $2,499*

    Cruise Line: Windstar Cruise

    Ship:  Star Pride

    Sailing Dates: Nov 12 2022 | Nov 19 2022 | Nov 26 2022 | Jan 07 2023 | Jan 14 2023 | Jan 21 2023 | Jan 28 2023 | Feb 04 2023 | Feb 11 2023 | Feb 18 2023 | Feb 25 2023 | Mar 04 2023

    Port: San Juan to San Juan

    ( Note: Optional tours are available from most ports for an additional charge. )

    14 days - Star Collector: Lovely Leewards [San Juan to San Juan]
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    7 Days - Windward Ways & Tobago Cays [Oranjestad to Bridgetown]

    7 Days - Windward Ways & Tobago Cays [Oranjestad to Bridgetown]
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    Starting from $2,499*

    Cruise Line: Windstar Cruise

    Ship:  Star Legend

    Sailing Dates: Jan 14 2023 | Feb 11 2023

    Port: Oranjestad to Bridgetown

    ( Note: Optional tours are available from most ports for an additional charge. )

    7 Days - Windward Ways & Tobago Cays [Oranjestad to Bridgetown]
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    7 days - Lush & Lovely Islands of the Lesser Antilles [St. Maarten to Bridgetown]

    7 days - Lush & Lovely Islands of the Lesser Antilles [St. Maarten to Bridgetown]
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    Starting from $2,499*

    Cruise Line: Windstar Cruise

    Ship:  Wind Surf

    Sailing Dates: Jan 28 2023 | Feb 25 2023

    Port: St. Maarten to Bridgetown

    ( Note: Optional tours are available from most ports for an additional charge. )

    7 days - Lush & Lovely Islands of the Lesser Antilles [St. Maarten to Bridgetown]
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    7 days - Jewels of the Windward Islands [Bridgetown to Bridgetown]

    7 days - Jewels of the Windward Islands [Bridgetown to Bridgetown]
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    Starting from $2,499*

    Cruise Line: Windstar Cruise

    Ship:  Wind Surf

    Sailing Dates: Feb 04 2023 | Mar 04 2023

    Port: Bridgetown to Bridgetown

    ( Note: Optional tours are available from most ports for an additional charge. )

    7 days - Jewels of the Windward Islands [Bridgetown to Bridgetown]
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    7 days - Lush & Lovely Islands of the Lesser Antilles [Bridgetown to St. Maarten]

    7 days - Lush & Lovely Islands of the Lesser Antilles [Bridgetown to St. Maarten]
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    Starting from $2,499*

    Cruise Line: Windstar Cruise

    Ship:  Wind Surf

    Sailing Dates: Feb 11 2023 | Mar 11 2023

    Port: Bridgetown to St. Maarten

    ( Note: Optional tours are available from most ports for an additional charge. )

    7 days - Lush & Lovely Islands of the Lesser Antilles [Bridgetown to St. Maarten]
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    7 days - Classic Caribbean [St. Maarten to St. Maarten]

    7 days - Classic Caribbean [St. Maarten to St. Maarten]
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    Starting from $2,599*

    Cruise Line: Windstar Cruise

    Ship:  Wind Surf

    Sailing Dates: Dec 10 2022 | Jan 14 2023 | Mar 25 2023 | Dec 09 2023 | Dec 23 2023 | Jan 06 2024 | Jan 20 2024 | Feb 03 2024 | Feb 17 2024 | Mar 02 2024 | Mar 16 2024

    Port: St. Maarten to St. Maarten

    ( Note: Optional tours are available from most ports for an additional charge. )

    7 days - Classic Caribbean [St. Maarten to St. Maarten]
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    7 days - Yachtsman's Caribbean [St. Maarten to St. Maarten]

    7 days - Yachtsman's Caribbean [St. Maarten to St. Maarten]
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    Starting from $2,599*

    Cruise Line: Windstar Cruise

    Ship:  Wind Surf

    Sailing Dates: Jan 07 2023 | Jan 21 2023 | Feb 18 2023 | Mar 18 2023

    Port: St. Maarten to St. Maarten

    ( Note: Optional tours are available from most ports for an additional charge. )

    7 days - Yachtsman's Caribbean [St. Maarten to St. Maarten]
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    7 Days - Beach Fun & Sun: A Remote Caribbean Getaway [St. Maarten to St. Maarten]

    7 Days - Beach Fun & Sun: A Remote Caribbean Getaway [St. Maarten to St. Maarten]
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    Starting from $2,599*

    Cruise Line: Windstar Cruise

    Ship:  Star Pride / Wind Surf

    Sailing Dates: Nov 04 2023 | Dec 16 2023 | Dec 30 2023 | Jan 13 2024 | Jan 27 2024 | Feb 10 2024 | Feb 24 2024 | Mar 09 2024 | Mar 23 2024

    Port: St. Maarten to St. Maarten

    ( Note: Optional tours are available from most ports for an additional charge. )

    7 Days - Beach Fun & Sun: A Remote Caribbean Getaway [St. Maarten to St. Maarten]
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    7 days - Windward Islands Surf & Sunsets [San Juan to San Juan]

    7 days - Windward Islands Surf & Sunsets [San Juan to San Juan]
    View Itinerary
    Starting from $2,999*

    Cruise Line: Windstar Cruise

    Ship:  Star Pride

    Sailing Dates: Nov 12 2022 | Nov 26 2022 | Jan 07 2023 | Jan 21 2023 | Feb 04 2023 | Feb 18 2023 | Mar 04 2023

    Port: San Juan to San Juan

    ( Note: Optional tours are available from most ports for an additional charge. )

    7 days - Windward Islands Surf & Sunsets [San Juan to San Juan]
    Book Now

    *Prices are per person, based on double occupancy. Prices do not include Government Fees & Taxes. Pricing and availability subject to change without notice. STIC Travel Group reserves the right to refuse or honor any prices / sailings that are erroneously printed or quoted. Terms & Conditions apply.

     
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