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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 you're 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 island's 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 UNESCO's 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:

14 days - Star Collector: Lovely Leewards

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Starting from $4,593*

Cruise Line: Windstar Cruise

Ship: Star Pride | Star Legend

Sailing Dates: Nov 08 2026 | Dec 06 2026 | Dec 27 2026 | Jan 03 2027 | Nov 01 2027 | Nov 08 2027 | Nov 15 2027 | Dec 20 2027 | Dec 27 2027 | Jan 10 2028 | Jan 17 2028 | Jan 24 2028 | Jan 31 2028 | Feb 07 2028 | Feb 14 2028 | Mar 13 2028 | Mar 20 2028

Port: San Juan to San Juan

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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	San Juan, Puerto Rico	07:00 AM

7 days - San Juan & the Virgin Islands

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Starting from $2,862*

Cruise Line: Windstar Cruise

Ship: Star Pride | Star Legend

Sailing Dates: Nov 15 2026 | Nov 29 2026 | Dec 13 2026 | Dec 27 2026 | Jan 10 2027 | Nov 01 2027 | Nov 15 2027 | Dec 20 2027 | Jan 03 2028 | Jan 17 2028 | Jan 31 2028 | Feb 14 2028 | Mar 20 2028

Port: San Juan to San Juan

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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 - Windward Ways & Tobago Cays [Bridgetown to Oranjestad]

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Starting from $3,519*

Cruise Line: Windstar Cruise

Ship: Star Legend

Sailing Dates: Dec 04 2026

Port: Bridgetown to Oranjestad

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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 - Windward Islands Surf & Sunsets

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Starting from $2,930*

Cruise Line: Windstar Cruise

Ship: Star Pride | Star Legend

Sailing Dates: Nov 08 2026 | Nov 22 2026 | Dec 06 2026 | Dec 20 2026 | Jan 03 2027 | Nov 08 2027 | Nov 22 2027 | Dec 27 2027 | Jan 10 2028 | Jan 24 2028 | Feb 07 2028 | Feb 21 2028 | Mar 13 2028 | Mar 27 2028

Port: San Juan to San Juan

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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 - Jewels of the Windward Islands

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Starting from $3,138*

Cruise Line: Windstar Cruise

Ship: Star Legend

Sailing Dates: Mar 15 2026 | Nov 27 2026

Port: Bridgetown to Bridgetown

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15 Days - Star Collector: Captivating Caribbean

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Starting from $5,658*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Nov 27 2026

Port: Bridgetown to Oranjestad

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14 days - Star Collector: Caribbean Explorations

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Starting from $4,519*

Cruise Line: Windstar Cruise

Ship: Wind Surf / Wind Spirit

Sailing Dates: Feb 07 2026 | Feb 28 2026 | Mar 14 2026 | Mar 21 2026 | Dec 19 2026 | Dec 26 2026 | Jan 02 2027 | Jan 09 2027 | Jan 16 2027 | Jan 23 2027 | Jan 30 2027 | Feb 06 2027 | Feb 13 2027 | Feb 20 2027 | Feb 27 2027 | Mar 06 2027 | Mar 13 2027 | Nov 28 2027 | Dec 05 2027 | Jan 09 2028 | Jan 16 2028 | Jan 23 2028 | Jan 30 2028 | Feb 06 2028 | Feb 13 2028 | Feb 20 2028 | Feb 27 2028 | Mar 05 2028

Port: Philipsburg, St. Maarten to Philipsburg, St. Maarten

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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

7 Days - Windward Ways & Tobago Cays

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Starting from $3,919*

Cruise Line: Windstar Cruise

Ship: Star Legend

Sailing Dates: Mar 15 2026 | Feb 22 2027

Port: Oranjestad to Bridgetown

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7 days - Classic Caribbean

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Starting from $3,051*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Feb 07 2026 | Feb 28 2026 | Mar 21 2026 | Dec 26 2026 | Jan 09 2027 | Jan 23 2027 | Feb 06 2027 | Feb 20 2027 | Mar 06 2027 | Mar 20 2027

Port: Philipsburg, St. Maarten to Philipsburg, St. Maarten

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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

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Starting from $3,267*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Feb 14 2026 | Feb 21 2026 | Mar 07 2026 | Mar 14 2026 | Mar 28 2026 | Dec 19 2026 | Jan 02 2027 | Jan 16 2027 | Jan 23 2027 | Feb 13 2027 | Feb 27 2027 | Mar 13 2027

Port: Philipsburg, St. Maarten to Philipsburg, St. Maarten

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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

14 days - Star Collector: Lovely Leewards

7 days - San Juan & the Virgin Islands

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

7 days - Windward Islands Surf & Sunsets

7 days - Jewels of the Windward Islands

15 Days - Star Collector: Captivating Caribbean

14 days - Star Collector: Caribbean Explorations

7 Days - Windward Ways & Tobago Cays

7 days - Classic Caribbean

7 Days - Beach Fun & Sun: A Remote Caribbean Getaway

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