Caribbean

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.
Candy-colored cocktails sipped in seaside watering holes. Carefree days followed by calypso-flavored nights. These ..read more
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11 Days - Colombian & Southern Caribbean Coastlines

Starting from $6,030*

Cruise Line: Windstar Cruise

Ship:  Wind Star / Wind Spirit

Sailing Dates:  Nov 24 2026

Port: Bridgetown to Colon

7 Days - Mind, Body and Spirit Collection: Bermuda Bliss

Starting from $2,926*

Cruise Line: Windstar cruises

Ship:  Star Pride

Sailing Dates:  Oct 20 2026

Port: New York City to San Juan

10 Days - Gems of the Leeward Islands

Starting from $4,257*

Cruise Line: Windstar Cruise

Ship:  Star Pride

Sailing Dates:  Oct 28 2026

Port: San Juan to San Juan

7 Days - Windward Island Delights

Starting from $3,399*

Cruise Line: Windstar cruises

Ship:  Wind Spirit

Sailing Dates:  Mar 07 2026 | Mar 21 2026

Port: Bridgetown to Bridgetown

14 days - Star Collector: Lovely Leewards - Star Seeker

Starting from $9,699*

Cruise Line: Windstar Cruise

Ship:  Star Seeker

Sailing Dates:  Feb 06 2026 | Feb 13 2026 | Feb 20 2026 | Feb 27 2026 | Mar 06 2026

Port: San Juan to San Juan

7 days - San Juan & the Virgin Islands - Star Seeker

Starting from $5,299*

Cruise Line: Windstar Cruise

Ship:  Star Seeker

Sailing Dates:  Feb 06 2026 | Feb 20 2026 | Mar 06 2026

Port: San Juan to San Juan

7 days - Windward Islands Surf & Sunsets - Star Seeker

Starting from $5,733*

Cruise Line: Windstar Cruise

Ship:  Star Seeker

Sailing Dates:  Feb 13 2026 | Feb 27 2026 | Mar 13 2026

Port: San Juan to San Juan

11 Days - Stars of the Greater Antilles

Starting from $4,399*

Cruise Line: Windstar Cruise

Ship:  Wind Surf

Sailing Dates: Feb 17 2026

Port: Cozumel to St. Maarten

10 Days - Gems of the Leeward Islands Star Seeker

Starting from $6,757*

Cruise Line: Windstar Cruise

Ship:  Star Seeker

Sailing Dates: Mar 27 2026

Port: San Juan to San Juan

*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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