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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 - Colors of Key West & Central America [Miami to Colón]

Starting from $1,599*

Cruise Line: Windstar Cruise

Ship: Star Breeze

Sailing Dates: Apr 22 2021

Port: Miami to Colón

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

14 Days - Star Collector: The Biggest Little Treasures of the Lesser Antilles

Starting from $1,999*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Jan 09 2021 | Jan 16 2021 | Feb 27 2021 | Mar 06 2021

Port: Bridgetown 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 02 2021 | Feb 20 2021 | Jan 15 2022

Port: St. Maarten to Bridgetown

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

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

Starting from $1,999*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Jan 30 2021 | Mar 20 2021

Port: Bridgetown 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: Dec 05 2020 | Dec 12 2020 | Dec 19 2020 | Feb 06 2021 | Mar 27 2021 | 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. )

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: Jan 23 2021 | Mar 13 2021 | Mar 12 2022

Port: Bridgetown to St. Maarten

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

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

Starting from $1,999*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Nov 29 2020

Port: St. Maarten to St. Maarten

( 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: Dec 26 2020 | Jan 08 2022

Port: St. Maarten to Bridgetown

( 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. )

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. )