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Caribbean

Caribbean

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

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

7-Day Eastern Caribbean

7-Day Eastern Caribbean

Starting from $699*

Cruise Line: Holland America Line

Ship: ms Eurodam

Sailing Dates: Feb 14 2021 | Mar 07 2021 | Mar 28 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 Eastern Caribbean

10-Day Panama Canal Sunfarer

10-Day Panama Canal Sunfarer

Starting from $1,079*

Cruise Line: Holland America Line

Ship: ms Zuiderdam

Sailing Dates: Feb 14 2021 | Mar 07 2021 | Mar 28 2021

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

11-Day Panama Canal Sunfarer

11-Day Panama Canal Sunfarer

Starting from $1,179*

Cruise Line: Holland America Line

Ship: ms Zuiderdam

Sailing Dates: Feb 03 2021 | Feb 24 2021 | Mar 17 2021 | Apr 07 2021

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

14-Day Eastern / Western Caribbean

14-Day Eastern / Western Caribbean

Starting from $1,339*

Cruise Line: Holland America Line

Ship: ms Eurodam

Sailing Dates: Feb 14 2021 | Mar 07 2021 | Mar 28 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 Eastern / Western Caribbean

11-Day Southern Caribbean Wayfarer

11-Day Southern Caribbean Wayfarer

Starting from $1,379*

Cruise Line: Holland America Line

Ship: ms Nieuw Statendam

Sailing Dates: Feb 17 2021 | Mar 10 2021 | Mar 31 2021

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

7-Day Western Caribbean

7-Day Western Caribbean

Starting from $699*

Cruise Line: Holland America Line

Ship: ms Eurodam

Sailing Dates: Jan 31 2021 | Feb 21 2021 | Mar 14 2021 | Apr 04 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

14-Day Western / Tropical Caribbean

14-Day Western / Tropical Caribbean

Starting from $1,389*

Cruise Line: Holland America Line

Ship: ms Eurodam

Sailing Dates: 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. )

14-Day Western / Tropical Caribbean

7-Day Western Caribbean

7-Day Western Caribbean

Starting from $749*

Cruise Line: Holland America Line

Ship: ms Nieuw Amsterdam

Sailing Dates: Feb 13 2021 | Apr 07 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

14-Day Western / Tropical Caribbean

14-Day Western / Tropical Caribbean

Starting from $1,339*

Cruise Line: Holland America Line

Ship: ms Nieuw Amsterdam

Sailing Dates:

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

7-Day Tropical Caribbean

7-Day Tropical Caribbean

Starting from $749*

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. )

7-Day Tropical Caribbean

10-Day Southern Caribbean Seafarer

10-Day Southern Caribbean Seafarer

Starting from $1,279*

Cruise Line: Holland America Line

Ship: ms Nieuw Statendam

Sailing Dates: 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. )

10-Day Southern Caribbean Seafarer

7-Day Eastern Caribbean

7-Day Eastern Caribbean

Starting from $649*

Cruise Line: Holland America Line

Ship: ms Nieuw Amsterdam

Sailing Dates: Feb 06 2021 | Feb 27 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 Eastern Caribbean

14-Day Eastern / Western Caribbean

14-Day Eastern / Western Caribbean

Starting from $1,239*

Cruise Line: Holland America Line

Ship: ms Nieuw Amsterdam

Sailing Dates: Feb 06 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 Eastern / Western Caribbean

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

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

Starting from $1,299*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Feb 13 2021 | Apr 03 2021 | Dec 11 2021 | Mar 05 2022 | Mar 19 2022

Port: St. Maarten to St. Maarten

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

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

Day	Port	Arrive	Depart
0	Philipsburg, St. Maarten		07:00 PM
1	Barbuda, Barbuda	08:00 AM	03:00 PM
2	Roseau, Dominica	08:00 AM	05:00 PM
3	Pigeon Island, St. Lucia	08:00 AM	04:00 PM
4	Les Saintes, Guadeloupe	08:00 AM	06:00 PM
5	Basseterre, St. Kitts	08:00 AM	10:00 PM
6	Gustavia, St. Barth�lemy	08:00 AM	10:00 PM
7	Philipsburg, St. Maarten	06:00 AM

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

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

Starting from $1,999*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: 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: Caribbean Explorations [St. Maarten to St. Maarten]

Day	Port	Arrive	Depart
0	Philipsburg, St. Maarten		07:00 PM
1	Barbuda, Barbuda	08:00 AM	03:00 PM
2	Roseau, Dominica	08:00 AM	05:00 PM
3	Pigeon Island, St. Lucia	08:00 AM	04:00 PM
4	Les Saintes, Guadeloupe	08:00 AM	06:00 PM
5	Basseterre, St. Kitts	08:00 AM	10:00 PM
6	Gustavia, St. Barth�lemy	08:00 AM	10:00 PM
7	Philipsburg, St. Maarten	06:00 AM	11:59 PM
8	Falmouth Harbour, Antigua	08:00 AM	10:00 PM
9	At Sea
10	Soper's Hole, Tortola, B.V.I.	08:00 AM	06:00 PM
10	Jost Van Dyke, Great Harbour, B.V.I.	07:00 AM	11:59 PM
11	Jost Van Dyke, Great Harbour, B.V.I.	12:01 AM	03:00 PM
11	Virgin Gorda, Prickly Pear Beach, B.V.I	06:00 PM	11:59 PM
12	Virgin Gorda, Prickly Pear Beach, B.V.I	12:01 AM	05:00 PM
13	Gustavia, St. Barth�lemy	08:00 AM	10:00 PM
14	Philipsburg, St. Maarten	06:00 AM

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

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

Starting from $1,499*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: 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 - Yachtsman's Caribbean [St. Maarten to St. Maarten]

Day	Port	Arrive	Depart
0	Philipsburg, St. Maarten		07:00 PM
1	Falmouth Harbour, Antigua	08:00 AM	10:00 PM
2	At Sea	�	�
3	Soper's Hole, Tortola, B.V.I.	08:00 AM	06:00 PM
3	Jost Van Dyke, Great Harbour, B.V.I.	07:00 AM	11:59 PM
4	Jost Van Dyke, Great Harbour, B.V.I.	12:01 AM	03:00 PM
4	Virgin Gorda, Prickly Pear Beach, B.V.I	06:00 AM	11:59 PM
5	Virgin Gorda, Prickly Pear Beach, B.V.I	12:01 AM	05:00 PM
6	Gustavia, St. Barth�lemy	08:00 AM	10:00 PM
7	Philipsburg, St. Maarten	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 $1,399*

Cruise Line: Windstar Cruise

Ship: Star Breeze / Star Pride

Sailing Dates: 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 - 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	�

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 $1,399*

Cruise Line: Windstar Cruise

Ship: Star Breeze / Star Pride

Sailing Dates: 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. )

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: Leeward & Windward Caribbean Havens [St. Maarten to Bridgetown]

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: Jan 08 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 [St. Maarten to Bridgetown]

7 days - Lush & Lovely Islands of the Lesser Antilles [St. Maarten to Bridgetown]

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: Feb 20 2021 | Jan 15 2022

Port: St. Maarten to Bridgetown

( 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]

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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.