7-Night Caribbean Cruise
Departs San Juan, Puerto Rico
Sailing Dec 13 - 20, 2026
Windstar Cruises - Star Pride
4.595 Reviews
Dates & Pricing
Currently Viewing
Sail DateDec 13 - 20, `26
Oceanview
$3,162
Unlock
Balcony
Balcony
Suite
$5,662
Similar Sailings
Sponsored
Cruise Itinerary
Cruise Itinerary
Departs San Juan, Puerto Rico
Sailing Dec 13 - 20, 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
Show More
Find a Cruise
Top Cruise Deals
Search by Destination
Cruises by Port
AmaWaterwaysAmerican Cruise LinesAtlas Ocean VoyagesAurora ExpeditionsAvalon WaterwaysAzamara CruisesCarnival CruisesCelebrity CruisesCelebrity River CruisesCelestyal CruisesCrystal CruisesCunardDisney CruisesExplora JourneysHolland AmericaHX CruisesMargaritaville at SeaMSC CruisesNorwegian Cruise LineOceania CruisesPaul Gauguin CruisesPonant ExplorationsPrincess CruisesRegent CruisesRivieria TravelRoyal CaribbeanScenic River CruisesSeabournSilverseaSwan HellenicTauck River CruisesViking Ocean CruisesViking River CruisesVirgin VoyagesWindstar Cruises
Don't Miss the Latest Deals!
- Save favorite vacations & searches
- Early access to promotions
- Exclusive deals, discounts & prices
- Plus more!
Talk to a Vacation Planner
Call at
1-888-447-8459
or click here to submit a form and we will connect you with an Independent Vacation Planner that specializes in the type of travel you are interested in. 
Why Choose Avoya?
From powerful online search, to specialized travel expertise, and exclusive deals and extras - discover what makes Avoya Travel a different, better type of travel company.