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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 youre sailing through turquoise waters, lazing on powdery white beaches, the glamorous harbors and unknown coves of this area remain a hidden treasure.

Explore Caribbean Cruises

Sort by: Sailing Date | Price | Cruise Line | Duration

14-Day Tropical / Eastern Caribbean

14-Day Tropical / Eastern Caribbean

Starting from $1,749*

Cruise Line: Holland America Line

Ship: ms Eurodam

Sailing Dates: Nov 01 | 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. )

14-Day Tropical / Eastern Caribbean

7-Day Eastern Caribbean

7-Day Eastern Caribbean

Starting from $799*

Cruise Line: Holland America Line

Ship: ms Nieuw Amsterdam

Sailing Dates: Oct 19 2019 | Nov 16 2019 | 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. )

7-Day Eastern Caribbean

14-Day Eastern / Tropical Caribbean

14-Day Eastern / Tropical Caribbean

Starting from $989*

Cruise Line: Holland America Line

Ship: ms Nieuw Amsterdam

Sailing Dates: Oct 19 2019

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 / Tropical Caribbean

10-Day Panama Canal Sunfarer

10-Day Panama Canal Sunfarer

Starting from $1,299*

Cruise Line: Holland America Line

Ship: ms Zuiderdam

Sailing Dates: Oct 20 2019 | Nov 10 2019 | Nov 20 2019 | 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. )

10-Day Panama Canal Sunfarer

7-DAY AUTHENTIC CUBA

7-DAY AUTHENTIC CUBA

Starting from $1,099*

Cruise Line: Holland America Line

Ship: ms Veendam

Sailing Dates: Oct 23 2019 | Oct 30 2019 | Nov 06 2019 | Nov 13 2019 | Nov 20 2019 | Nov 27 2019 | Dec 04 2019 | Dec 11 2019 | Jan 08 2020 | Jan 15 2020 | Jan 22 2020 | Jan 29 2020 | Feb 05 2020 | Feb 12 2020 | Feb 19 2020 | Feb 26 2020 | Mar 04 2020 | Mar 11 2020 | Mar 18 2020 | Mar 25 2020 | Apr 01 2020 | Apr 08 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 AUTHENTIC CUBA

Day	Port	Arrive	Depart
0	Fort Lauderdale, Florida, US		04:00 PM
1	Havana (La Habana), Cuba	08:00 AM	�
2	Havana (La Habana), Cuba	�	02:00 AM
2	At Sea	�	�
3	Cienfuegos, Cuba	08:00 AM	05:00 PM
4	Ocho Rios, Jamaica	10:00 AM	05:00 PM
5	Georgetown, Cayman Islands	08:00 AM	05:00 PM
6	At Sea	�	�
7	Fort Lauderdale, Florida, US	07:00 AM	�

7-Day Tropical Caribbean

7-Day Tropical Caribbean

Starting from $799*

Cruise Line: Holland America Line

Ship: ms Nieuw Amsterdam

Sailing Dates: Oct 26 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 Tropical Caribbean

7 days - The Spanish Main: Rise of the New World [Colï¿½n to San Juan]

7 days - The Spanish Main: Rise of the New World [Col�n to San Juan]

Starting from $1,599*

Cruise Line: Windstar Cruise

Ship: Star Legend

Sailing Dates: Oct 26 2019

Port: Colï¿½n to San Juan

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

7 days - The Spanish Main: Rise of the New World [Col�n to San Juan]

11-Day Panama Canal Sunfarer

11-Day Panama Canal Sunfarer

Starting from $1,499*

Cruise Line: Holland America Line

Ship: ms Zuiderdam

Sailing Dates: Oct 30 2019 | 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. )

11-Day Panama Canal Sunfarer

10-Day Southern Caribbean Seafarer

10-Day Southern Caribbean Seafarer

Starting from $672*

Cruise Line: Holland America Line

Ship: ms Volendam

Sailing Dates: Nov 01 2019

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

7 days - San Juan & the Virgin Islands [San Juan to San Juan]

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: Nov 02 2019 | Nov 16 2019 | Nov 30 2019 | 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 days - San Juan & the Virgin Islands [San Juan to San Juan]

Day	Port	Arrive	Depart
0	San Juan, Puerto Rico		10:00 PM
1	Vieques, Puerto Rico	08:00 AM	09:00 PM
2	Gustavia, St. Barth�lemy	11:00 AM	10:00 PM
3	Little Bay, Montserrat, BWI	08:00 AM	05:00 PM
4	Philipsburg, St. Maarten	07:00 AM	10:00 PM
5	Jost Van Dyke, Great Harbour, B.V.I.	08:00 AM	11:59 PM
6	Virgin Gorda, Prickly Pear Beach, B.V.I	08:00 AM	05:00 PM
7	San Juan, Puerto Rico	07:00 AM

14 days - Star Collector: Lovely Leewards [San Juan to San Juan]

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: Nov 02 2019 | Nov 09 2019 | Nov 16 2019 | Nov 23 2019 | Nov 30 2019 | Dec 07 2019 | 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. )

14 days - Star Collector: Lovely Leewards [San Juan to San Juan]

Day	Port	Arrive	Depart
0	San Juan, Puerto Rico		07:00 PM
1	Philipsburg, St. Maarten	12:00 PM	05:00 PM
2	Les Saintes, Guadeloupe	08:00 AM	05:00 PM
3	Bequia, St. Vincent & the Grenadines	10:00 AM	10:00 PM
4	St. George's, Grenada	08:00 AM	06:00 PM
5	Pigeon Island, St. Lucia	08:00 AM	04:00 PM
6	At Sea	�	�
7	San Juan, Puerto Rico	07:00 AM	11:59 PM
8	Vieques, Puerto Rico	08:00 AM	09:00 PM
9	Philipsburg, St. Maarten	11:00 AM	10:00 PM
10	Little Bay, Montserrat, BWI	08:00 AM	05:00 PM
11	Gustavia, St. Barth�lemy	07:00 AM	10:00 PM
12	Jost Van Dyke, Great Harbour, B.V.I.	08:00 AM	11:59 PM
13	Virgin Gorda, Prickly Pear Beach, B.V.I	08:00 AM	05:00 PM
14	San Juan, Puerto Rico	07:00 AM

12-Day Stars Of The Cuban Sky

12-Day Stars Of The Cuban Sky

Starting from $7,499*

Cruise Line: Seabourn Cruise

Ship: Seabourn Sojourn

Sailing Dates: Nov 04 2019

Port: Miami, Florida, US to Miami, Florida, US

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

12-Day Stars Of The Cuban Sky

14-Day Authentic Cuba / Eastern Caribbean

14-Day Authentic Cuba / Eastern Caribbean

Starting from $2,099*

Cruise Line: Holland America Line

Ship: ms Veendam

Sailing Dates: Nov 06 2019 | Nov 27 2019

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

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

14-Day Authentic Cuba / Eastern Caribbean

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

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

Starting from $1,999*

Cruise Line: Windstar Cruise

Ship: Star Pride

Sailing Dates: Nov 06 2019 | Feb 15 2020

Port: San Juan to Bridgetown

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

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

Day	Port	Arrive	Depart
0	San Juan, Puerto Rico		09:00 PM
1	Vieques, Puerto Rico	08:00 AM	10:00 PM
2	Philipsburg, St. Maarten	12:00 PM	10:00 PM
3	Little Bay, Montserrat, BWI	08:00 AM	05:00 PM
4	Roseau, Dominica	08:00 AM	06:00 PM
5	Pigeon Island, St. Lucia	08:00 AM	06:00 PM
6	St. George's, Grenada	08:00 AM	01:00 PM
7	Bridgetown, Barbados	05:00 AM	�

7 days - Windward Islands Surf & Sunsets [San Juan to San Juan]

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: Nov 09 2019 | Nov 23 2019 | Dec 07 2019 | 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. )

7 days - Windward Islands Surf & Sunsets [San Juan to San Juan]

Day	Port	Arrive	Depart
0	San Juan, Puerto Rico		07:00 PM
1	Philipsburg, St. Maarten	12:00 PM	05:00 PM
2	Les Saintes, Guadeloupe	08:00 AM	05:00 PM
3	Bequia, St. Vincent & the Grenadines	10:00 AM	10:00 PM
4	St. George's, Grenada	08:00 AM	06:00 PM
5	Pigeon Island, St. Lucia	08:00 AM	04:00 PM
6	At Sea	�	�
7	San Juan, Puerto Rico	07:00 AM	�

9-Day Eastern Caribbean Seafarer

9-Day Eastern Caribbean Seafarer

Starting from $543*

Cruise Line: Holland America Line

Ship: ms Volendam

Sailing Dates: Nov 11 2019

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

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

9-Day Eastern Caribbean Seafarer

7-Day Eastern Caribbean

7-Day Eastern Caribbean

Starting from $1,049*

Cruise Line: Holland America Line

Ship: ms Veendam

Sailing Dates: Nov 13 2019 | Dec 04 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

11-Day Southern Caribbean Wayfarer

11-Day Southern Caribbean Wayfarer

Starting from $1,399*

Cruise Line: Holland America Line

Ship: ms Koningsdam

Sailing Dates: Nov 13 2019 | 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 Southern Caribbean Wayfarer

14-Day Eastern Caribbean / Authentic Cuba

14-Day Eastern Caribbean / Authentic Cuba

Starting from $2,099*

Cruise Line: Holland America Line

Ship: ms Veendam

Sailing Dates: Nov 13 2019 | Dec 04 2019

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 Caribbean / Authentic Cuba

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

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

Starting from $1,699*

Cruise Line: Windstar Cruise

Ship: ï¿½Star Pride

Sailing Dates: Nov 13 2019 | Feb 22 2020

Port: Bridgetown to San Juan

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

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

Day	Port	Arrive	Depart
0	Bridgetown, Barbados		06:00 PM
1	Bequia, St. Vincent & the Grenadines	08:00 AM	07:00 PM
2	Castries, St. Lucia	07:00 AM	10:00 PM
3	Les Saintes, Guadeloupe	09:00 AM	06:00 PM
4	Basseterre, St. Kitts	08:00 AM	10:00 PM
5	Gustavia, St. Barth�lemy	08:00 AM	10:00 PM
6	Virgin Gorda, Prickly Pear Beach, B.V.I	08:00 AM	05:00 PM
7	San Juan, Puerto Rico	07:00 AM

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*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.