11-night Eastern Caribbean: Windward & Leeward Islands Cruise From Fort Lauderdale, Florida

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An aerial view of the colorful waterfront of St. John's, Antigua, with a long pier extending into the calm, blue sea and the town's charming buildings and marina in the background.
Holland America's Oosterdam sailing in Alaska.
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Sailing Dec 11, 2027

from $1,884 per person* taxes and fees included

Your 11-night Caribbean Cruise at a Glance

Sailings aboard Oosterdam depart from Fort Lauderdale, Florida with 7 stops in ports-of-call including St. Maarten (Philipsburg), Basseterre, St. Kitts, and Roseau, Dominica. The Cruise Web can help you find the best deals and stateroom prices on the next sailing December 11, 2027.

Fort Lauderdale is a popular destination offering scenic beaches, a network of canals, and a lively atmosphere with excellent shopping, dining options. Before you depart Fort Lauderdale, Florida, we can help you plan travel and accommodations for your Caribbean cruise.

Destination

Caribbean

Stops on your Caribbean voyage will include Basseterre, St. Kitts on day 5 and Half Moon Cay on day 11. We can help you with excursions and making the most of any itinerary.

Cruise Ship

Oosterdam

Oosterdam, built in 2003 and refurbished in 2026, carries 1,964 passengers with a crew of 817. Ask us about dining options like Lido Market and entertainment like Billboard Onboard!

Amazing food and superb service make Holland America one of the longest running cruise lines. We can help you maximize deals on Caribbean cruises aboard Oosterdam or 10 of Holland America’s other ships.