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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:

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

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Starting from $2,499*

Cruise Line: Windstar Cruise

Ship: Star Pride | Star Seeker

Sailing Dates: Nov 01 2025 | Nov 15 2025 | Nov 30 2025 | Jan 23 2026 | Feb 06 2026 | Feb 20 2026 | Mar 06 2026 | Nov 15 2026 | Nov 15 2026 | Dec 13 2026 | Dec 27 2026 | Jan 10 2027

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

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

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Starting from $3,999*

Cruise Line: Windstar Cruise

Ship: Star Pride | Star Seeker

Sailing Dates: Nov 02 2025 | Nov 09 2025 | Nov 16 2025 | Nov 23 2025 | Jan 23 2026 | Jan 30 2026 | Feb 06 2026 | Feb 13 2026 | Feb 20 2026 | Feb 27 2026 | Mar 06 2026 | Nov 08 2026 | Dec 06 2026 | Dec 27 2026 | Jan 03 2027

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

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Starting from $2,499*

Cruise Line: Windstar Cruise

Ship: Star Pride | Star Seeker

Sailing Dates: Jan 30 2026 | Feb 13 2026 | Feb 27 2026 | Mar 13 2026 | Nov 08 2026 | Nov 22 2026 | Dec 06 2026 | Dec 20 2026 | Jan 03 2027

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 [Bridgetown to Bridgetown]

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Starting from $2,599*

Cruise Line: Windstar Cruise

Ship: Wind Surf / Star Pride / Wind Spirit

Sailing Dates: Jan 18 2026 | Mar 07 2026 | Mar 21 2026

Port: Bridgetown to Bridgetown

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

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Starting from $3,699*

Cruise Line: Windstar Cruise

Ship: Wind Surf / Wind Spirit

Sailing Dates: Dec 07 2025 | Dec 14 2025 | Dec 21 2025 | Jan 31 2026 | Feb 07 2026 | Feb 28 2026 | Mar 14 2026 | Mar 21 2026

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 [Oranjestad to Bridgetown]

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Starting from $2,599*

Cruise Line: Windstar Cruise

Ship: Star Pride / Wind Surf

Sailing Dates: Jan 25 2026

Port: Oranjestad to Bridgetown

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

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Starting from $2,299*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Dec 21 2025 | Feb 07 2026 | Feb 28 2026 | Mar 21 2026

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

6 Days - Beach Fun & Sun: A Remote Caribbean Getaway [Philipsburg, St. Maarten to Philips]

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Starting from $2,399*

Cruise Line: Windstar Cruise

Ship: Wind Spirit / Wind Surf

Sailing Dates: Dec 14 2025 | Dec 28 2025 | Jan 04 2026 | Jan 24 2026 | Jan 31 2026 | Feb 14 2026 | Feb 21 2026 | Mar 07 2026 | Mar 14 2026 | Mar 28 2026

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

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

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Starting from $3,499*

Cruise Line: Windstar Cruise

Ship: Wind Star | Wind Spirit

Sailing Dates: Nov 18 2025 | Nov 24 2026

Port: Bridgetown to Colon

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5 Days - Barefoot Break in the British Virgin Islands [Philipsburg, St. Maarten to Philip]

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Starting from $2,099*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Dec 02 2025

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

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Day	Port	Arrive	Depart
0	St. Maarten		06:00 PM
1	SOPER'S HOLE,JOST VAN DYKE, GREAT HARBOUR	12:00 PM	05:00 PM
2	JOST VAN DYKE, GREAT HARBOUR	09:00 AM	06:00 PM
3	VIRGIN GORDA / PRICKLY PEAR	9:00 AM	6:00 PM
4	Gustavia	ï¿½	ï¿½
5	St. Maarten	07:00 AM	ï¿½

*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 - San Juan & the Virgin Islands [San Juan to San Juan]

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

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

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

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

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

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

6 Days - Beach Fun & Sun: A Remote Caribbean Getaway [Philipsburg, St. Maarten to Philips]

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

5 Days - Barefoot Break in the British Virgin Islands [Philipsburg, St. Maarten to Philip]

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