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Caribbean
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    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 Islands Surf & Sunsets - Star Seeker

    7 days - Windward Islands Surf & Sunsets - Star Seeker
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    Starting from $5,162*

    Cruise Line: Windstar Cruise

    Ship:  Star Seeker

    Sailing Dates:  Mar 13 2026

    Port: San Juan to San Juan

    7 days - Windward Islands Surf & Sunsets - Star Seeker
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    7 Days - New World Caribbean Trio - Star Seeker

    7 Days - New World Caribbean Trio - Star Seeker
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    Starting from $4,426*

    Cruise Line: Windstar Cruise

    Ship:  Star Seeker

    Sailing Dates: Apr 06 2026

    Port: San Juan to Colon

    7 Days - New World Caribbean Trio - Star Seeker
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    10 Days - Gems of the Leeward Islands

    10 Days - Gems of the Leeward Islands
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    Starting from $4,257*

    Cruise Line: Windstar Cruise

    Ship:  Star Pride

    Sailing Dates:  Oct 28 2026

    Port: San Juan to San Juan

    10 Days - Gems of the Leeward Islands
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    10 Days - Gems of the Leeward Islands Star Seeker

    10 Days - Gems of the Leeward Islands Star Seeker
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    Starting from $6,757*

    Cruise Line: Windstar Cruise

    Ship:  Star Seeker

    Sailing Dates: Mar 27 2026

    Port: San Juan to San Juan

    10 Days - Gems of the Leeward Islands Star Seeker
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    11 Days - Colombian & Southern Caribbean Coastlines

    11 Days - Colombian & Southern Caribbean Coastlines
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    Starting from $6,030*

    Cruise Line: Windstar Cruise

    Ship:  Wind Star / Wind Spirit

    Sailing Dates:  Nov 24 2026

    Port: Bridgetown to Colon

    11 Days - Colombian & Southern Caribbean Coastlines
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    14 days - Star Collector: Lovely Leewards

    14 days - Star Collector: Lovely Leewards
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    Starting from $4,593*

    Cruise Line: Windstar Cruise

    Ship:  Star Pride | Star Legend

    Sailing Dates:  Nov 08 2026 | Dec 06 2026 | Dec 27 2026 | Jan 03 2027 | Nov 01 2027 | Nov 08 2027 | Nov 15 2027 | Dec 20 2027 | Dec 27 2027 | Jan 10 2028 | Jan 17 2028 | Jan 24 2028 | Jan 31 2028 | Feb 07 2028 | Feb 14 2028 | Mar 13 2028 | Mar 20 2028

    Port: San Juan to San Juan

    14 days - Star Collector: Lovely Leewards
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    14 days - Star Collector: Caribbean Explorations

    14 days - Star Collector: Caribbean Explorations
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    Starting from $4,519*

    Cruise Line: Windstar Cruise

    Ship:  Wind Surf / Wind Spirit

    Sailing Dates:  Mar 14 2026 | Mar 21 2026 | Dec 19 2026 | Dec 26 2026 | Jan 02 2027 | Jan 09 2027 | Jan 16 2027 | Jan 23 2027 | Jan 30 2027 | Feb 06 2027 | Feb 13 2027 | Feb 20 2027 | Feb 27 2027 | Mar 06 2027 | Mar 13 2027 | Nov 28 2027 | Dec 05 2027 | Jan 09 2028 | Jan 16 2028 | Jan 23 2028 | Jan 30 2028 | Feb 06 2028 | Feb 13 2028 | Feb 20 2028 | Feb 27 2028 | Mar 05 2028

    Port: Philipsburg, St. Maarten to Philipsburg, St. Maarten

    14 days - Star Collector: Caribbean Explorations
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    14 days - Star Collector: Lovely Leewards - Star Seeker

    14 days - Star Collector: Lovely Leewards - Star Seeker
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    Starting from $11,296*

    Cruise Line: Windstar Cruise

    Ship:  Star Seeker

    Sailing Dates:  Mar 06 2026

    Port: San Juan to San Juan

    14 days - Star Collector: Lovely Leewards - Star Seeker
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    15 Days - Star Collector: Captivating Caribbean

    15 Days - Star Collector: Captivating Caribbean
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    Starting from $5,658*

    Cruise Line: Windstar Cruise

    Ship:  Wind Surf

    Sailing Dates:  Nov 27 2026

    Port: Bridgetown to Oranjestad

    15 Days - Star Collector: Captivating Caribbean
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    *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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