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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8 Days - In the Wake of the Spanish Armadas [Oranjestad to Colon]

Starting from $3,299*

Cruise Line: Windstar Cruise

Ship:  Wind Surf

Sailing Dates: Feb 01 2026

Port: Oranjestad to Colon

11 Days - Stars of the Greater Antilles [Cozumel to St. Maarten]

Starting from $3,999*

Cruise Line: Windstar Cruise

Ship:  Wind Surf

Sailing Dates: Feb 17 2026

Port: Cozumel to St. Maarten

6 Days - Panama's Pristine Caribbean[Colon to Oranjestad]

Starting from $2,399*

Cruise Line: Windstar cruises

Ship:  Star Pride

Sailing Dates: Mar 09 2026

Port: Colon to Oranjestad

7 Days - New World Caribbean Trio[San Juan to Colon]

Starting from $3,399*

Cruise Line: Windstar cruises

Ship:  Star Seeker

Sailing Dates: Apr 06 2026

Port: San Juan to Colon

10 Days - Sublime Southern Caribbean[Bridgetown to Philipsburg, St. Maarten]

Starting from $3,399*

Cruise Line: Windstar cruises

Ship:  Wind Spirit

Sailing Dates: Jan 04 2027

Port: Bridgetown to Philipsburg, St. Maarten

*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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