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14-Night Caribbean

14 Nights Eastern Caribbean Cruise

Aboard Star Pride — Windstar

Departs San Juan

Day-by-Day Itinerary

Departs 07:00 PM

Embark

Tours & Excursions

Arrives 08:00 AM · Departs 06:00 PM

Port Call

Arrives 08:00 AM · Departs 10:00 PM

Port Call

Arrives 08:00 AM · Departs 05:00 PM

Port Call

Tours & Excursions

Arrives 08:00 AM · Departs 10:00 PM

Port Call

Tours & Excursions

Arrives 09:00 AM · Departs 10:00 PM

Port Call

Arrives 08:00 AM · Departs 05:00 PM

Port Call

Arrives 07:00 AM · Departs 07:00 PM

Port Call

Tours & Excursions

Arrives 09:00 AM · Departs 10:00 PM

Port Call

Tours & Excursions

Arrives 08:00 AM · Departs 10:00 PM

Port Call

Tours & Excursions

Arrives 08:00 AM · Departs 04:30 PM

Port Call

Arrives 11:00 AM · Departs 06:00 PM

Port Call

Arrives 08:00 AM · Departs 03:00 PM

Port Call

Arrives 07:00 AM

Disembark

Tours & Excursions

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Port Guides On This Route

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San Juan St. John Gustavia Basseterre Philipsburg Great Harbour BVI Virgin Gorda St. George’s Bequia Mayreau

Browse Destination Hubs

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Windstar port guides All Star Pride sailings Caribbean cruise ports Puerto Rico U.S. Virgin Islands Sint Maarten British Virgin Islands United Kingdom Grenada Guadeloupe France

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Upcoming Sailings

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From $5,904 per person

Nov 29, 2026 14 nights from $5,904

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Star Pride

Star Plus Class
Built 1988
312 guests