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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 [Bridgetown to Oranjestad]

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Starting from $1,799*

Cruise Line: Windstar Cruise

Ship: Star Breeze / Star Legend

Sailing Dates: Feb 18 2023

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

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

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Starting from $2,499*

Cruise Line: Windstar Cruise

Ship: Star Pride

Sailing Dates: Feb 04 2023 | Feb 11 2023 | Feb 18 2023 | Feb 25 2023 | Mar 04 2023

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

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Starting from $2,999*

Cruise Line: Windstar Cruise

Ship: Star Pride

Sailing Dates: Feb 04 2023 | Feb 18 2023 | Mar 04 2023

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	ï¿½

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: Feb 11 2023 | Feb 25 2023 | Mar 11 2023

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

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: Mar 25 2023 | Dec 09 2023 | Dec 23 2023 | Jan 06 2024 | Jan 20 2024 | Feb 03 2024 | Feb 17 2024 | Mar 02 2024 | Mar 16 2024

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

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Starting from $2,599*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Feb 18 2023 | Mar 18 2023

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	Falmouth Harbour, Antigua	08:00 AM	10:00 PM
2	At Sea	ï¿½	ï¿½
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. Barthï¿½lemy	08:00 AM	10:00 PM
7	Philipsburg, St. Maarten	05:00 AM	ï¿½

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

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Starting from $2,499*

Cruise Line: Windstar Cruise

Ship: Star Legend

Sailing Dates: Feb 11 2023

Port: Oranjestad to Bridgetown

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

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14 Days - Star Collector: Leeward & Windward Caribbean Havens [St. Maarten to Bridgetown]

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Starting from $3,999*

Cruise Line: Windstar Cruise

Ship: Star Breeze / Wind Surf

Sailing Dates: Feb 18 2023

Port: St. Maarten to Bridgetown

( 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 $2,499*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Feb 25 2023

Port: St. Maarten to Bridgetown

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

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

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Starting from $2,499*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Feb 04 2023 | Mar 04 2023

Port: Bridgetown 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 [Bridgetown to Oranjestad]

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

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

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

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

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

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

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 - Jewels of the Windward Islands [Bridgetown to Bridgetown]

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