7-Night Caribbean Cruise
Departs San Juan, Puerto Rico
Sailing Dec 27, 2026 - Jan 3, 2027
Windstar Cruises - Star Pride
4.595 Reviews
Dates & Pricing
Currently Viewing
Sail DateDec 27, `26 - Jan 03, `27
Oceanview
$4,262
Unlock
Balcony
Balcony
Suite
$6,262
Similar Sailings
Sponsored
Cruise Itinerary
Cruise Itinerary
Departs San Juan, Puerto Rico
Sailing Dec 27, 2026 - Jan 3, 2027
Day 1
Dec 27
San Juan
Puerto Rico
Departs 11:59PM
Day 2
Dec 28
Saint John
Us Virgin Islands (Cruz Bay)
Arrives 8:00AM | Departs 11:59PM
Day 3
Dec 29
Saint Barthelemy (Gustavia)
Guadeloupe
Arrives 8:00AM | Departs 11:59PM
Day 4
Dec 30
Saint Kitts And Nevis (Basse Terre)
Arrives 8:00AM | Departs 11:59PM
Day 5
Dec 31
Saint Maarten (Phillipsburg)
Netherlands Antilles
Arrives 8:00AM | Departs 11:59PM
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.