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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.
 
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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. )

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. )

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. )

10 days - Central America Revealed [Colón to Miami]

Starting from $2,399*

Cruise Line: Windstar Cruise

Ship: Star Legend

Sailing Dates: Apr 02 2022

Port: Colón to Miami

( 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. )

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. )

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. )