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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.
 
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7 days - Classic Caribbean [St. Maarten to St. Maarten]

Starting from $1,299*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates:  Dec 11 2021 | Mar 05 2022 | Mar 19 2022

Port: St. Maarten to St. Maarten

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

14 days - Star Collector: Caribbean Explorations [St. Maarten to St. Maarten]

Starting from $1,999*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates:  Mar 05 2022 | Mar 12 2022 | Mar 19 2022

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]

Starting from $1,499*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates:  Jan 08 2022 | Mar 12 2022 | Mar 26 2022

Port: St. Maarten to St. Maarten

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

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

Starting from $1,399*

Cruise Line: Windstar Cruise

Ship: Star Breeze / Star Pride

Sailing Dates:  NOV 20 2021 | Dec 04 2021 | Jan 15 2022 | Jan 29 2022 | Feb 12 2022 | Feb 26 2022 | Mar 12 2022

Port: San Juan to San Juan

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

7 days - San Juan & the Virgin Islands [San Juan to San Juan]

Starting from $1,399*

Cruise Line: Windstar Cruise

Ship: Star Breeze / Star Pride

Sailing Dates:  Nov 13 2021 | Nov 27 2021 | Dec 11 2021 | Jan 08 2022 | Feb 05 2022 | Feb 19 2022

Port: San Juan to San Juan

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

14 Days - Star Collector: Leeward & Windward Caribbean Havens [St. Maarten to Bridgetown]

Starting from $2,199*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates:  Jan 08 2022

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]

Starting from $1,399*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates:  Jan 15 2022

Port: St. Maarten to Bridgetown

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

14 Days - Star Collector: Antilles Adventures [St. Maarten to Bridgetown]

Starting from $1,999*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates:  Jan 15 2022

Port: St. Maarten to Bridgetown

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

7 days - Jewels of the Windward Islands [Bridgetown to Bridgetown]

Starting from $1,499*

Cruise Line: Windstar Cruise

Ship: Wind Surf / Wind Star

Sailing Dates:  Jan 22 2022 | Feb 26 2022 | Mar 05 2022 | Mar 12 2022

Port: Bridgetown to Bridgetown

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

14 Days - Star Collector: Antilles Adventures [Bridgetown to St. Maarten]

Starting from $1,999*

Cruise Line: Windstar Cruise

Ship: Wind Surf / Wind Star

Sailing Dates:  Mar 12 2022

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]

Starting from $1,399*

Cruise Line: Windstar Cruise

Ship: Wind Surf / Wind Star

Sailing Dates:  Mar 19 2022

Port: Bridgetown to St. Maarten

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

10 Days - Gems of the Leeward Islands [San Juan to San Juan]

Starting from $2,299*

Cruise Line: Windstar Cruise

Ship: Star Pride

Sailing Dates: Nov 03 2021 | Dec 18 2021

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]

Starting from $2,599*

Cruise Line: Windstar Cruise

Ship: Star Pride

Sailing Dates: Nov 13 2021 | Nov 20 2021 | Nov 27 2021 | Dec 04 2021 | Jan 08 2022 | Jan 15 2022 | Jan 22 2022 | Jan 29 2022 | Feb 05 2022 | Feb 12 2022 | Feb 19 2022 | Feb 26 2022 | Mar 05 2022

Port: San Juan to San Juan

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

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

Starting from $2,299*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Dec 18 2021

Port: St. Maarten to St. Maarten

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

10 days - Central America Revealed [Miami to Colón]

Starting from $2,399*

Cruise Line: Windstar Cruise

Ship: Star Legend

Sailing Dates: Dec 19 2021

Port: Miami to Colón

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

11 Days - Caribbean Pleasures [St. Maarten to St. Maarten]

Starting from $2,699*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Dec 28 2021

Port: St. Maarten to St. Maarten

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

14 Days - Star Collector: Captivating Caribbean [Bridgetown to Oranjestad]

Starting from $4,399*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Jan 22 2022

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]

Starting from $2,499*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Jan 29 2022

Port: Bridgetown to Oranjestad

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

9 Days - In the Wake of the Spanish Armadas [Oranjestad to Colón]

Starting from $2,199*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Feb 05 2022

Port: Oranjestad to Colón

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

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

Starting from $2,299*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Feb 22 2022

Port: Cozumel to St. Maarten

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

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