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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

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7 Days - Windward Ways & Tobago Cays [Oranjestad to Bridgetown]

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Starting from $2,299*

Cruise Line: Windstar Cruise

Ship: Star Legend / Star Pride

Sailing Dates: Jan 13 2024 | Feb 10 2024 | Mar 09 2024 | Jan 04 2025 | Feb 15 2025

Port: Oranjestad to Bridgetown

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

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7 Days - Windward Ways & Tobago Cays [Bridgetown to Oranjestad]

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Starting from $2,299*

Cruise Line: Windstar Cruise

Ship: Star Legend / Star Pride

Sailing Dates: Nov 25 2023 | Jan 20 2024 | Dec 14 2024 | Jan 11 2025 | Feb 22 2025

Port: Bridgetown to Oranjestad

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

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Day	Port	Arrive	Depart
0	Hong Kong, China		ï¿½
1	Hong Kong, China	ï¿½	07:00 AM
2	Xiamen, China	08:00 AM	06:00 PM
3	AT SEA	ï¿½	ï¿½
4	Hundred Islands, Philippines	08:00 AM	05:00 PM
5	Manila, Philippines	10:00 AM	ï¿½
6	Manila, Philippines	ï¿½	06:00 PM
7	Boracay, Philippines	10:00 AM	06:00 PM
8	Coron, Philippines	07:00 AM	04:00 PM
9	Puerto Princesa, Philippines	08:00 AM	06:00 PM
10	AT SEA	ï¿½	ï¿½
11	Kota Kinabalu, Sabahlaem, Malaysia	08:00 AM	06:00 PM
12	AT SEA	ï¿½	ï¿½
13	AT SEA	ï¿½	ï¿½
14	Singapore	07:00 AM	ï¿½

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

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Starting from $2,399*

Cruise Line: Windstar Cruise

Ship: Wind Surf / Star Pride

Sailing Dates: Nov 11 2023

Port: St. Maarten to Bridgetown

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

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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 - Jewels of the Windward Islands [Bridgetown to Bridgetown]

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Starting from $2,699*

Cruise Line: Windstar Cruise

Ship: Wind Surf / Star Pride / Wind Spirit

Sailing Dates: Nov 18 2023 | Mar 21 2024 | Mar 28 2024 | Dec 07 2024 | Dec 21 2024 | Jan 04 2025 | Jan 18 2025 | Feb 01 2025 | Feb 15 2025

Port: Bridgetown to Bridgetown

( 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

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

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Starting from $2,999*

Cruise Line: Windstar Cruise

Ship: Star Pride

Sailing Dates: Nov 03 2024 | Nov 16 2024 | Nov 23 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	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	ï¿½	ï¿½
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. Barthï¿½lemy	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

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

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Starting from $2,999*

Cruise Line: Windstar Cruise

Ship: Star Pride

Sailing Dates: Nov 16 2024 | Nov 30 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	San Juan, Puerto Rico		10:00 PM
1	Vieques, Puerto Rico	08:00 AM	09:00 PM
2	Gustavia, St. Barthï¿½lemy	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

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

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

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Starting from $2,999*

Cruise Line: Windstar Cruise

Ship: Wind Star / Wind Spirit

Sailing Dates: Mar 10 2024 | Mar 16 2024 | Mar 15 2025

Port: ColÃ³n to Bridgetown

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

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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. 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 - Windward Ways & Tobago Cays [Oranjestad to Bridgetown]

7 Days - Windward Ways & Tobago Cays [Bridgetown to Oranjestad]

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

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

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

7 days - Jewels of the Windward Islands [Bridgetown to Bridgetown]

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

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

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

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

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