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Caribbean Cruises

Caribbean Cruises

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 Tropical / Eastern Caribbean

Starting from $1,749*

Cruise Line: Holland America Line

Ship: ms Eurodam

Sailing Dates:  2020 | 2021 | 2021 | 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. )

7-Day Western Caribbean

Starting from $444*

Cruise Line: Holland America Line

Ship: ms Veendam

Sailing Dates:  Dec 11 2019 | Jan 08 2020 | Feb 12 2020 | Feb 26 2020 | Mar 11 2020 | Apr 08 2020

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

( 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 $2,199*

Cruise Line: Windstar Cruise

Ship: Star Pride / Star Legend

Sailing Dates:  Dec 21 2019 | Jan 04 2020 | Jan 18 2020 | Feb 01 2020 | Mar 07 2020 | Mar 21 2020 | Dec 19 2020 | Jan 02 2021 | Jan 16 2021 | Jan 30 2021 | Feb 13 2021 | Feb 27 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 $3,699*

Cruise Line: Windstar Cruise

Ship: Star Pride / Star Legend

Sailing Dates:  Dec 14 2019 | Dec 21 2019 | Dec 28 2019 | Jan 04 2020 | Jan 11 2020 | Jan 18 2020 | Feb 01 2020 | Feb 29 2020 | Mar 07 2020 | Mar 14 2020 | Dec 12 2020 | Dec 19 2020 | Dec 26 2020 | Jan 02 2021 | Jan 09 2021 | Jan 16 2021 | Jan 23 2021 | Jan 30 2021 | Feb 06 2021 | Feb 13 2021 | Feb 20 2021 | Feb 27 2021

Port: San Juan to San Juan

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

7-Day Classic Yachtsman's Caribbean

Starting from $1,999*

Cruise Line: Seabourn Cruise

Ship: Seabourn Odyssey

Sailing Dates:  Dec 14 2019

Port: Philipsburg, Sint Maarten to Bridgetown, Barbados

( 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 $2,199*

Cruise Line: Windstar Cruise

Ship: Star Pride / Star Legend

Sailing Dates:  Dec 14 2019 | Dec 28 2019 | Jan 11 2020 | Jan 25 2020 | Feb 08 2020 | Feb 29 2020 | Mar 14 2020 | Jan 23 2021 | Feb 06 2021 | Feb 20 2021 | Mar 06 2021

Port: San Juan to San Juan

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

7-Day Eastern Caribbean

Starting from $414*

Cruise Line: Holland America Line

Ship: ms Veendam

Sailing Dates:  Jan 15 2020 | Feb 05 2020 | Feb 19 2020 | Mar 04 2020 | Apr 01 2020 | Apr 15 2020

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

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

7-Day Western Caribbean

Starting from $494*

Cruise Line: Holland America Line

Ship: ms Nieuw Statendam

Sailing Dates:  Dec 08 2019

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

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

7-Day Eastern Caribbean

Starting from $487*

Cruise Line: Holland America Line

Ship: ms Nieuw Amsterdam

Sailing Dates:  Dec 14 2019 | Jan 11 2020

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

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

11-Day Southern Caribbean Wayfarer

Starting from $1,399*

Cruise Line: Holland America Line

Ship: ms Koningsdam

Sailing Dates:  Jan 22 2020 | Feb 12 2020 | Mar 04 2020

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

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

11-Day Panama Canal Sunfarer

Starting from $890*

Cruise Line: Holland America Line

Ship: ms Zuiderdam

Sailing Dates:  Feb 15 2020 | Feb 26 2020 | Mar 18 2020 | Apr 08 2020

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

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

7 days - Winter Antilles Escape [San Juan to Bridgetown]

Starting from $1,999*

Cruise Line: Windstar Cruise

Ship: Star Pride

Sailing Dates:  Feb 15 2020

Port: San Juan to Bridgetown

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

7 days - Antilles Island Hopping [Bridgetown to San Juan]

Starting from $1,699*

Cruise Line: Windstar Cruise

Ship: ï¿½Star Pride

Sailing Dates:  Feb 22 2020

Port: Bridgetown to San Juan

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

7-Day Tropical Caribbean

Starting from $523*

Cruise Line: Holland America Line

Ship: ms Nieuw Amsterdam

Sailing Dates:  Feb 15 2020 | Feb 29 2020 | Mar 28 2020

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

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

7-Day Tropical Caribbean

Starting from $494*

Cruise Line: Holland America Line

Ship: ms Nieuw Statendam

Sailing Dates:  Dec 15 2019 | Jan 05 2020 | Jan 26 2020 | Feb 16 2020 | Mar 08 2020 | Mar 29 2020

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

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

7-Day Eastern Caribbean

Starting from $520*

Cruise Line: Holland America Line

Ship: ms Nieuw Statendam

Sailing Dates:  Apr 05 2020

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

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

10-Day Southern Caribbean Seafarer

Starting from $593*

Cruise Line: Holland America Line

Ship: ms Zuiderdam

Sailing Dates: Dec 10 2019

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

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

11-Day Gems Of The Antilles

Starting from $2,399*

Cruise Line: Seabourn Cruise

Ship: Seabourn Sojourn

Sailing Dates: Dec 10 2019

Port: Miami, Florida, US to San Juan, Puerto Rico

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

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

Starting from $2,199*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Dec 14 2019 | Dec 28 2019 | Dec 05 2020 | Dec 19 2020 | Feb 29 2020 | Mar 14 2020 | Mar 28 2020 | Feb 13 2021 | Apr 03 2021

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 $3,199*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Dec 14 2019 | Dec 21 2019 | Dec 28 2019 | Dec 05 2020 | Dec 12 2020 | Dec 19 2020 | Feb 29 2020 | Mar 07 2020 | Mar 14 2020 | Mar 21 2020 | Feb 06 2021 | Mar 27 2021

Port: St. Maarten 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.