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 the Mediterranean and Alaska 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 6 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
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One page with the route, the day-by-day schedule, typical weather and a notes box for each day.
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 Oct 13, 2026