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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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7 days - Windward Islands Surf & Sunsets

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Starting from $2,338*

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

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Starting from $2,399*

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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7 days - Classic Caribbean

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Starting from $2,399*

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

7 Days - Mind, Body and Spirit Collection: Bermuda Bliss

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Starting from $2,399*

Cruise Line: Windstar cruises

Ship: Star Pride

Sailing Dates: Oct 19 2025

Port: New York City to San Juan

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6 Days - Panama's Pristine Caribbean

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Starting from $2,399*

Cruise Line: Windstar cruises

Ship: Star Pride

Sailing Dates: Mar 09 2026

Port: Colon to Oranjestad

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7 days - San Juan & the Virgin Islands

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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

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

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Starting from $2,499*

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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7 Days - Windward Ways & Tobago Cays

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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 - Windward Island Delights

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Starting from $2,599*

Cruise Line: Windstar cruises

Ship: Wind Spirit

Sailing Dates: Dec 28 2025 | Mar 07 2026

Port: Bridgetown to Bridgetown

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8 Days - In the Wake of the Spanish Armadas

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Starting from $3,299*

Cruise Line: Windstar Cruise

Ship: Wind Surf

Sailing Dates: Feb 01 2026

Port: Oranjestad to Colon

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Day	Port	Arrive	Depart
0	ORANJESTAD		06:00 PM
1	AT SEA	12:00 PM	05:00 PM
2	SANTA MARTA	09:00 AM	06:00 PM
3	CARTAGENA	9:00 AM	6:00 PM
4	AT SEA	9:00 AM	6:00 PM
5	BOCAS DEL TORO	9:00 AM	6:00 PM
6	AT SEA	9:00 AM	6:00 PM
7	COLÃN	ï¿½	ï¿½
8	COLÃN	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 - Windward Islands Surf & Sunsets

7 days - Jewels of the Windward Islands

7 days - Classic Caribbean

7 Days - Mind, Body and Spirit Collection: Bermuda Bliss

6 Days - Panama's Pristine Caribbean

7 days - San Juan & the Virgin Islands

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

7 Days - Windward Ways & Tobago Cays

7 Days - Windward Island Delights

8 Days - In the Wake of the Spanish Armadas

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