14-Night Caribbean Cruise
Departs San Juan, Puerto Rico
Sailing Nov 15 - 29, 2026
Windstar Cruises - Star Pride
4.595 Reviews
Dates & Pricing
Sail DateNov 15 - 29, `26
Oceanview
$5,393
Balcony
$7,813
Suite
$10,293
Similar Sailings
Sponsored
Cruise Itinerary
Cruise Itinerary
Departs San Juan, Puerto Rico
Sailing Nov 15 - 29, 2026
Day 1
Nov 15
San Juan
Puerto Rico, United States
Departs 7:00pm
Day 2
Nov 16
Cruz Bay
St. John, United States Virgin Islands
Arrives 8:00am | Departs 6:00pm
Day 3
Nov 17
Basseterre
St. Kitts, St. Kitts And Nevis
Arrives 8:00am | Departs 5:00pm
Day 4
Nov 18
Gustavia
Saint Barthélemy, France
Arrives 7:00am | Departs 10:00pm
Day 5
Nov 19
Philipsburg
Sint Maarten
Arrives 8:00am | Departs 10:00pm
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