_m.webp)
15-Night Caribbean Cruise
Departs Saint Maarten (Phillipsburg), Netherlands Antilles
Sailing Dec 19, 2027 - Jan 3, 2028
Windstar Cruises - Wind Surf
4.7148 Reviews
Dates & Pricing
Currently Viewing
Sail DateDec 19, `27 - Jan 03, `28
Oceanview
$5,219
Suite
$10,919
Similar Sailings
Sponsored
Cruise Itinerary
Cruise Itinerary
Departs Saint Maarten (Phillipsburg), Netherlands Antilles
Sailing Dec 19, 2027 - Jan 3, 2028
Day 1
Dec 19
Saint Maarten (Phillipsburg)
Netherlands Antilles
Departs 11:59pm
Day 2
Dec 20
San Jose
Costa Rica
Arrives 8:00am | Departs 11:59pm
Day 3
Dec 21
Saint Barthelemy (Gustavia)
Guadeloupe
Arrives 8:00am | Departs 11:59pm
Day 4
Dec 22
Road Bay
Arrives 8:00am | Departs 11:59pm
Day 5
Dec 23
Jost Van Dyke
British Virgin Islands
Arrives 7:00pm | 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.