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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Departure Date:

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

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Starting from $1,299*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Dec 05 2020 | Dec 19 2020 | 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. )

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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

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

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Starting from $1,399*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Nov 29 2020

Port: St. Maarten to St. Maarten

( 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 $1,399*

Cruise Line: Windstar Cruise

Ship: Star Breeze

Sailing Dates: Dec 13 2020

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

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

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Starting from $1,399*

Cruise Line: Windstar Cruise

Ship: Star Breeze / Star Pride

Sailing Dates: Dec 19 2020 | Jan 02 2021 | Jan 16 2021 | 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. )

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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 $1,399*

Cruise Line: Windstar Cruise

Ship: Star Breeze / Star Pride

Sailing Dates: Dec 26 2020 | Jan 09 2021 | Jan 23 2021 | 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. )

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

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Starting from $1,399*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Jan 02 2021 | Feb 20 2021 | Jan 15 2022

Port: St. Maarten to Bridgetown

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

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7 days - Uncovering the Windward Wonders of the Caribbean [Bridgetown to Bridgetown]

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Starting from $1,399*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Jan 16 2021 | Mar 06 2021

Port: Bridgetown to Bridgetown

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

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Day	Port	Arrive	Depart
0	Vancouver, B.C., CA		04:00 PM
1	Scenic Cruising The Inside Passage
2	Ketchikan, Alaska, US	07:00 AM	03:00 PM
3	Juneau, Alaska, US	10:00 AM	10:00 PM
4	Skagway, Alaska, US	07:00 AM	09:00 PM
5	Glacier Bay	07:00 AM	05:00 PM
6	AT SEA	ï¿½	ï¿½
7	Seward (Anchorage), Alaska, US	04:30 AM

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

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Starting from $1,399*

Cruise Line: Windstar Cruise

Ship: Wind Surf / Wind Star

Sailing Dates: Jan 30 2021 | Mar 20 2021 | Mar 19 2022

Port: Bridgetown to St. Maarten

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

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

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Starting from $1,499*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Dec 12 2020 | Dec 26 2020 | 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. )

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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 - Jewels of the Windward Islands [Bridgetown to Bridgetown]

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Starting from $1,499*

Cruise Line: Windstar Cruise

Ship: Wind Surf / Wind Star

Sailing Dates: Jan 09 2021 | Jan 23 2021 | Feb 27 2021 | Mar 13 2021 | Jan 22 2022 | Feb 26 2022 | Mar 05 2022 | Mar 12 2022

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 Travels Private Limited reserves the right to refuse or honor any prices / sailings that are erroneously printed or quoted. Terms & Conditions apply.

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