14-Night Caribbean Cruise
Departs San Juan, Puerto Rico
Sailing Nov 29 - Dec 13, 2026
Windstar Cruises - Star Pride
4.595 Reviews
Dates & Pricing
Currently Viewing
Sail DateNov 29 - Dec 13, `26
Oceanview
$5,393
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Balcony
Balcony
Suite
$10,293
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Cruise Itinerary
Cruise Itinerary
Departs San Juan, Puerto Rico
Sailing Nov 29 - Dec 13, 2026
Day 1
Nov 29
San Juan
Puerto Rico, United States
Departs 7:00PM
Day 2
Nov 30
Cruz Bay
St. John, United States Virgin Islands
Arrives 8:00AM | Departs 6:00PM
Day 3
Dec 1
Gustavia
Saint Barthélemy, France
Arrives 8:00AM | Departs 10:00PM
Day 4
Dec 2
Basseterre
St. Kitts, St. Kitts And Nevis
Arrives 8:00AM | Departs 5:00PM
Day 5
Dec 3
Philipsburg
Sint Maarten
Arrives 8:00AM | Departs 10:00PM
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