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

While Cuba has been off-limits to most American travelers since 1963, in recent years cruise ships have started calling again and flights from the United States have resumed. Most visitors today are drawn not only by the islandâs mild climate and beautiful beaches but also its cultural riches. Havana has a wealth of colonial buildings and vintage automobiles, as well as intimate paladares that serve local dishes and street parties that move to the rhythms of mambo and salsa. On the country's southern coast, Cienfuegos has elegant mansions and a 19th-century street plan that earned it a place on UNESCOâs list of World Heritage sites.

Explore Caribbean

Candy-colored cocktails sipped in seaside watering holes. Carefree days followed by calypso-flavored nights. These ..read more

Sort by: Sailing Date | Price | Duration

Departure Date:

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

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Starting from $2,599*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Dec 09 2023 | Dec 23 2023 | Jan 06 2024 | Jan 20 2024 | Feb 03 2024 | Feb 17 2024 | Mar 02 2024 | Mar 16 2024 | Dec 21 2024 | Jan 04 2025 | Jan 18 2025 | Jan 25 2025 | Feb 08 2025 | Feb 22 2025 | Mar 01 2025 | Mar 15 2025

Port: St. Maarten to St. Maarten

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

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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. Barthï¿½lemy	08:00 AM	10:00 PM
7	Philipsburg, St. Maarten	06:00 AM

7 Days - Beach Fun & Sun: A Remote Caribbean Getaway [St. Maarten to St. Maarten]

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Starting from $2,299*

Cruise Line: Windstar Cruise

Ship: Star Pride / Wind Surf

Sailing Dates: Nov 04 2023 | Dec 16 2023 | Dec 30 2023 | Jan 13 2024 | Jan 27 2024 | Feb 10 2024 | Feb 24 2024 | Mar 09 2024 | Mar 23 2024 | Dec 28 2024 | Jan 11 2025 | Feb 01 2025 | Feb 15 2025 | Mar 08 2025 | Mar 22 2025

Port: St. Maarten to St. Maarten

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

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14 Days - Star Collector: Captivating Caribbean [Bridgetown to Oranjestad]

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Starting from $3,699*

Cruise Line: Windstar Cruise

Ship: Star Pride

Sailing Dates: Nov 18 2023

Port: Bridgetown to Oranjestad

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

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

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Starting from $3,599*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Dec 09 2023 | Dec 16 2023 | Dec 23 2023 | Dec 30 2023 | Jan 06 2024 | Jan 13 2024 | Jan 20 2024 | Jan 27 2024 | Feb 03 2024 | Feb 10 2024 | Feb 17 2024 | Feb 24 2024 | Mar 02 2024 | Mar 09 2024 | Mar 16 2024 | Dec 21 2024 | Dec 28 2024 | Jan 04 2025 | Jan 11 2025 | Jan 25 2025 | Feb 01 2025 | Feb 08 2025 | Feb 15 2025 | Mar 01 2025 | Mar 08 2025 | Mar 15 2025

Port: St. Maarten to St. Maarten

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

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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. Barthï¿½lemy	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. Barthï¿½lemy	08:00 AM	10:00 PM
14	Philipsburg, St. Maarten	06:00 AM

11 Days - Colombian & Southern Caribbean Coastlines [Bridgetown to ColÃ³n]

11 Days - Colombian & Southern Caribbean Coastlines [Bridgetown to Colón]

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Starting from $2,999*

Cruise Line: Windstar Cruise

Ship: Wind Star

Sailing Dates: Dec 19 2023 | Nov 19 2024

Port: Bridgetown to ColÃ³n

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

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

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Starting from $2,799*

Cruise Line: Windstar Cruise

Ship: Star Pride

Sailing Dates: Nov 03 2024

Port: San Juan to San Juan

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

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Day	Port	Arrive	Depart
0	Fort Lauderdale, Florida, US		05:00 PM
1	Days at Sea	ï¿½	ï¿½
2	Amber Cove, Dominican Republic	10:00 AM	06:00 PM
3	San Juan, Puerto Rico	01:00 AM	11:00 PM
4	St. Thomas, U.S.V.I.	08:00 AM	05:00 PM
5	Days at Sea	ï¿½	ï¿½
6	Half Moon Cay, Bahamas	08:00 AM	03:00 PM
7	Fort Lauderdale, Florida, US	07:00 AM

*Prices are per person, based on double occupancy. Prices do not include Government Fees & Taxes. Pricing and availability subject to change without notice. STIC Travel Group reserves the right to refuse or honor any prices / sailings that are erroneously printed or quoted. Terms & Conditions apply.

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Caribbean

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

7 Days - Beach Fun & Sun: A Remote Caribbean Getaway [St. Maarten to St. Maarten]

14 Days - Star Collector: Captivating Caribbean [Bridgetown to Oranjestad]

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

11 Days - Colombian & Southern Caribbean Coastlines [Bridgetown to ColÃ³n]

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

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