Holland America Announces 2027-28 Caribbean Schedule
Holland America has revealed its 2027-2028 Caribbean schedule, which includes 29 itineraries across 47 departures. Voyages will range from five to 28 days, with a variety of sailings in the eastern, western, and southern Caribbean, as well as to the Panama Canal. Across the season, ships are scheduled to visit 35 ports in 25 countries and territories.
Throughout the Caribbean season, passengers can expect experiences designed to help them connect more deeply with the region, both aboard the ship and while ashore. Shore excursions curated with The History Channel will be offered, as well as local-focused “Meet the Makers” tours. On board, Holland America’s Destination Dining program and the Global Fresh Fish Program will reflect the flavors of the Caribbean.
Oosterdam‘s Transformation
Starting in December 2027, travelers will have the opportunity to experience the renovated Oosterdam — the first ship to debut as part of Holland America’s Evolution investment. It will debut new Solo Verandah staterooms with private balconies and dedicated workspace, as well as premium options such as the Bridgeview Suites and Vista Suites. The transformation will also add the all-day venue Grand Dutch Café. Oosterdam will operate longer voyages across the southern Caribbean and Panama Canal.
Half Moon Cay
Nearly every sailing on the 2027-2028 Caribbean schedule includes a visit to RelaxAway, Half Moon Cay, Carnival Corporation’s private Bahamian island. The enhanced tropical paradise features a new beach club, a refreshed Lobster Shack, expanded cabanas and villas, new activities such as pickleball, new shops, and new beverage experiences including Aperol spritz tricycles and Bacardi beach buggies.
Pan Am 100th Anniversary Cruise
A highlight of the season will be the 28-day Pan Am 100th Anniversary Legendary Voyage aboard Zuiderdam, departing October 30, 2027 roundtrip from Miami. 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. Nearly half of the itinerary will feature destinations that were part of Pan Am’s original network, allowing passengers the opportunity to follow in the footsteps of one of travel’s most iconic brands while exploring both well-known and hidden-gem ports.
The itinerary will include stops in Nassau, Bahamas, and San Juan, Puerto Rico, two early hubs in Pan Am’s Caribbean network. Other calls include Willemstad, Curaçao; Cartagena, Colombia; and Colón, Panama. The voyage also includes multiple consecutive port days in parts of the Caribbean, giving visitors more time in the destination compared to shorter itineraries.
