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 - Boston Sights, Warm Caribbean Nights [Boston to San Juan]

Starting from $2,599*

Cruise Line: Windstar Cruise

Ship:  Star Pride

Sailing Dates: Oct 23 2024 | Oct 18 2025

Port: Boston to San Juan

10 Days - Hidden Treasures of the Lesser Antilles [ Bridgetown to Bridgetown]

Starting from $2,899*

Cruise Line: Windstar Cruise

Ship:  Wind Spirit

Sailing Dates: Nov 27 2024

Port: Bridgetown to Bridgetown

5 Days - Barefoot Break in the British Virgin Islands [St. Maarten to St. Maarten]

Starting from $1,899*

Cruise Line: Windstar Cruise

Ship:  Wind Surf

Sailing Dates: Dec 02 2025

Port: St. Maarten to St. Maarten

21 Days - Star Collector: A Lesser Antilles Odyssey [St. Maarten to Bridgetown]

Starting from $6,099*

Cruise Line: Windstar Cruise

Ship:  Wind Surf Wind Spirit

Sailing Dates: Jan 04 2026 | Feb 21 2026

Port: St. Maarten to Bridgetown

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

Starting from $2,299*

Cruise Line: Windstar Cruise

Ship:  Wind Surf \ Wind Spirit

Sailing Dates: Jan 07 2026 | Jan 11 2026 | Feb 28 2026

Port: St. Maarten to Bridgetown

10 Days - Blue Waters of the Leeward Islands [St. Maarten to St. Maarten]

Starting from $3,499*

Cruise Line: Windstar Cruise

Ship:  Wind Spirit

Sailing Dates: Jan 14 2026

Port: St. Maarten to St. Maarten

17 Days - Star Collector: Hidden Gems of the Caribbean [St. Maarten to St. Maarten]

Starting from $4,799*

Cruise Line: Windstar Cruise

Ship:  Wind Spirit

Sailing Dates: Jan 14 2026

Port: St. Maarten to St. Maarten

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

Starting from $3,199*

Cruise Line: Windstar Cruise

Ship:  Wind Surf

Sailing Dates: Feb 01 2026

Port: Oranjestad to Colon

*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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