11 Night Eastern Caribbean: Windward & Leeward Islands Cruise aboard the Holland America Oosterdam
Prepare for eleven nights of relaxing sailing around the Caribbean when you embark on the Holland America Oosterdam from Fort Lauderdale and back again.
While aboard this trip you'll stop at favorite ports like San Juan in addition to rare ports like Roseau. This route is a special one for the Oosterdam, As it sails it only once.
We include all all taxes and fees in this price, so there are no surprises.
The Holland America Oosterdam
Based in Fort Lauderdale and refurbished less than one year ago in 2025, over 2,000 travelers can cruise on this top-rated Vista class cruise ship.
The Oosterdam Holland America boasts a gym, a spa, five jacuzzis, and a casino.
- Ship class
- Vista
- Built
- 2003
- Refurbished
- 2025
- Guests
- 2,024
- Crew
- 817
- Length
- 935 ft
Your Itinerary
This cruise consists of three sea days and seven port days. Highlights include long stops in Fort-de-France and Philipsburg as well as visits to very uncommon stops like Roseau.
© OpenStreetMap · © ESA WorldCover
Book Your Cruise
Since being listed 28 days ago, the cost of this sailing has remained steady at $1,829. Right now this itinerary is at an all time low, so secure your cabin now before it increases.
Photos show a typical cabin in each class. Layout and decor vary by category.
Resources
Add it to your calendar
Your departure and return dates in the calendar you already use.
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OutlookPrintable CruiseSheet
One page with the route, the day-by-day schedule, typical weather and a notes box for each day.
Wifi and Cell Service
GigSky offers plans that cover internet on and off the ship at a fraction of the Holland America price. For this cruise, get a 12-day plan for only $153.42. The connection works onboard and on shore.
Your plan includes 500MB per day of high speed data, plus unlimited messaging, rideshare, maps, and email.
Alternate Sailings
The Oosterdam sails this route once next year, but doesn't sail it this year. This is the only ship that sails this exact route.
No other departures of this route are on sale right now.
Show alternate dates for this cruise → Show all cruises that sail this route →
Data as of Nov 3, 2026