14-Night Caribbean Cruise
Departs San Juan, Puerto Rico
Sailing Dec 13 - 27, 2026
Windstar Cruises - Star Pride
4.595 Reviews
Dates & Pricing
Currently Viewing
Sail DateDec 13 - 27, `26
Oceanview
$5,193
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Balcony
Balcony
Suite
$10,093
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Cruise Itinerary
Cruise Itinerary
Departs San Juan, Puerto Rico
Sailing Dec 13 - 27, 2026
Day 1
Dec 13
San Juan
Puerto Rico, United States
Departs 7:00pm
Day 2
Dec 14
Cruz Bay
St. John, United States Virgin Islands
Arrives 8:00am | Departs 6:00pm
Day 3
Dec 15
Gustavia
Saint Barthélemy, France
Arrives 8:00am | Departs 10:00pm
Day 4
Dec 16
Basseterre
St. Kitts, St. Kitts And Nevis
Arrives 8:00am | Departs 5:00pm
Day 5
Dec 17
Philipsburg
Sint Maarten
Arrives 8:00am | Departs 10:00pm
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