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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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14-Day Western / Tropical Caribbean

Starting from $1,389*

Cruise Line: Holland America Line

Ship: ms Eurodam

Sailing Dates: Nov 15 2020 | Jan 31 2021 | Feb 21 2021 | Mar 14 2021

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

( 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 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. )

6 Days - San Juan & the Virgin Islands [San Juan to San Juan]

Starting from $1,399*

Cruise Line: Windstar Cruise

Ship: Star Breeze

Sailing Dates: Dec 13 2020

Port: San Juan to San Juan

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

7 days - Uncovering the Windward Wonders of the Caribbean [Bridgetown to Bridgetown]

Starting from $1,399*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Jan 16 2021 | Mar 06 2021

Port: Bridgetown to Bridgetown

( 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: Jan 30 2021 | Mar 20 2021 | Mar 19 2022

Port: Bridgetown 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: Dec 19 2020 | Jan 02 2021 | Jan 16 2021 | Jan 30 2021 | Feb 27 2021 | Mar 13 2021 | Mar 27 2021 | 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: Dec 26 2020 | Jan 09 2021 | Jan 23 2021 | Feb 06 2021 | Mar 06 2021 | Mar 20 2021 | 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. )

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

Starting from $1,399*

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-Day Western / Tropical Caribbean

Starting from $1,479*

Cruise Line: Holland America Line

Ship: ms Nieuw Amsterdam

Sailing Dates: Jan 23 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 $1,499*

Cruise Line: Holland America Line

Ship: ms Nieuw Amsterdam

Sailing Dates: Jan 09 2021

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

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