8-Night Caribbean Cruise
Departs Boston, Massachusetts
Sailing Oct 20 - 28, 2026
Windstar Cruises - Star Pride
4.595 Reviews
Dates & Pricing
Currently Viewing
Sail DateOct 20 - 28, `26
Oceanview
$2,926
Unlock
Balcony
Balcony
Suite
$5,426
Similar Sailings
Sponsored
Cruise Itinerary
Cruise Itinerary
Departs San Juan, Puerto Rico
Sailing Oct 20 - 28, 2026
Day 1
Oct 20
Boston
Massachusetts, United States
Departs 5:00pm
Day 2
Oct 21
At Sea
Day 3
Oct 22
At Sea
Day 4
Oct 23
Hamilton
Bermuda
Arrives 8:45am
Day 5
Oct 24
Hamilton
Bermuda
Departs 7:00am
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.