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Caribbean
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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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7 days - Yachtsman's Caribbean [St. Maarten to St. Maarten]

Starting from $1,499*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Dec 12 2020 | Dec 26 2020 | Feb 06 2021 | Mar 27 2021 | 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 - Jewels of the Windward Islands [Bridgetown to Bridgetown]

Starting from $1,499*

Cruise Line: Windstar Cruise

Ship: Wind Surf / Wind Star

Sailing Dates: Jan 09 2021 | Jan 23 2021 | Feb 27 2021 | Mar 13 2021 | 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. )

9 Days - The Allure of the Antilles [San Juan to Miami]

Starting from $1,499*

Cruise Line: Windstar Cruise

Ship: Star Breeze

Sailing Dates: Apr 03 2021

Port: San Juan to Miami

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

14-Day Tropical / Eastern Caribbean

Starting from $1,519*

Cruise Line: Holland America Line

Ship: ms Nieuw Amsterdam

Sailing Dates: Jan 30 2021

Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

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

14-Day Tropical / Eastern Caribbean

Starting from $1,519*

Cruise Line: Holland America Line

Ship: ms Eurodam

Sailing Dates: Feb 07 2021 | Feb 28 2021 | Mar 21 2021

Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

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

14-Day Western & Tropical Caribbean Holiday

Starting from $1,519*

Cruise Line: Holland America Line

Ship: ms Nieuw Amsterdam

Sailing Dates: Dec 12 2020

Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

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

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-Day Eastern & Western Caribbean Holiday

Starting from $1,709*

Cruise Line: Holland America Line

Ship: ms Nieuw Amsterdam

Sailing Dates: Dec 26 2020

Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

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

14-Day Eastern & Western Caribbean Holiday

Starting from $1,899*

Cruise Line: Holland America Line

Ship: ms Nieuw Statendam

Sailing Dates: Dec 23 2020

Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

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

14-Day Tropical & Eastern Caribbean Holiday

Starting from $1,999*

Cruise Line: Holland America Line

Ship: ms Nieuw Amsterdam

Sailing Dates: Dec 19 2020

Port: Fort Lauderdale, Florida, US to Fort Lauderdale, Florida, US

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