Holland America Line has unveiled its 2027/28 Caribbean season, spanning 29 itineraries across 47 departures from October 2027 through March 2028.
The line will be visiting 35 ports in 25 countries and territories across the Eastern, Western and Southern Caribbean and the Panama Canal.
Paul Grigsby, Holland America Line Vice President of Deployment and Revenue Planning, said the season gave guests more ways to experience the Caribbean than ever before.
“With more Caribbean itineraries of nine days or longer than any other cruise line, guests have more time to explore each destination and relax at our private island,” Mr Grigsby said.
A highlight of the season is the 28-day Pan Am 100th Anniversary Legendary Voyage aboard Zuiderdam, departing Miami on October 30, 2027.
Created in partnership with Pan Am, the sailing traces the airline’s historic Clipper flying boat routes across the Caribbean, Mexico and Latin America, visiting 19 ports in 13 countries including Nassau, San Juan, Willemstad and Cartagena.

The season also introduces the reimagined Oosterdam, the first ship to debut as part of Holland America Line’s Evolution investment, sailing the Caribbean from December 2027.
New features include Solo Verandah staterooms with private balconies, Bridgeview Suites with panoramic ocean views, Vista Suites and the Grand Dutch Café, an all-day venue inspired by the line’s Dutch heritage.
RelaxAway, Half Moon Cay, the line’s private island, features on nearly every itinerary and has been enhanced with a new beach club offering waiter service, priority tendering and exclusive food and beverage options, alongside refreshed cabanas, a new Lobster Shack and Aperol spritz tricycles.
Eight holiday cruises are available during the season, including a seven-day Eastern Caribbean departure aboard Rotterdam on December 22, 2027, and an 11-day Southern Caribbean Holiday aboard Oosterdam also departing December 22.




