Holland America Opens 2027-28 Caribbean Season With Longer Routes

Holland America Line has opened bookings for its 2027-28 Caribbean season, putting longer sailings at the center of a 47-departure deployment scheduled from October 2027 through March 2028. The program spans 29 itineraries ranging from five to 28 days, with calls at 35 ports in 25 countries and territories.

The schedule is built around extended Eastern, Western and Southern Caribbean routes, including more itineraries of nine days or longer than Holland America Line says any other cruise line will offer in the region that season.

Longer routes stretch the Caribbean map

Eurodam, Oosterdam, Rotterdam, Volendam and Zuiderdam will operate the season, with departures primarily from Fort Lauderdale and Miami. Nearly every itinerary includes a call at RelaxAway, Half Moon Cay, the line’s private destination in The Bahamas.

“We’ve built this season to give guests more ways to experience the Caribbean,” said Paul Grigsby, vice president, deployment and revenue planning for Holland America Line.

Southern Caribbean sailings include Aruba, Bonaire and Curacao, while Eastern Caribbean itineraries call at destinations such as Puerto Rico, the U.S. Virgin Islands and St. Maarten. Western Caribbean voyages include calls in Jamaica, Belize, Honduras and Mexico.

The season also includes 12-day Panama Canal Discovery cruises with a partial transit of the canal, including the locks and Gatun Lake, along with calls in Colombia, Costa Rica and the Cayman Islands. Eight holiday departures are scheduled for Thanksgiving, Christmas and New Year’s sailings across multiple ships.

The longest Caribbean offering is the 28-day Pan Am 100th Anniversary Legendary Voyage on Zuiderdam, departing Miami on Oct. 30, 2027. Created with Pan Am, the roundtrip voyage visits 19 ports in 13 countries while following portions of the airline’s historic Caribbean routes.

Oosterdam will introduce Evolution upgrades in the Caribbean

Oosterdam will join the Caribbean program in December 2027 after a multi-week dry dock at Fincantieri’s Palermo yard in Italy. The 2003-built, 81,769-gross-ton ship carries about 1,965 passengers at double occupancy and will be the first vessel to complete work under Holland America Line’s $500 million Evolution modernization program.

The program covers six Vista and Signature Class ships. Individual schedules for the other five ships have not been finalized, and the work is focused on interiors, venues and cabin categories, with no ship lengthening or additional decks planned.

Oosterdam’s changes will include Solo Verandah staterooms with private balconies and dedicated workspaces, along with Bridgeview Suites, Vista Suites and the addition of the Grand Dutch Café. During the season, the ship is scheduled to operate longer Southern Caribbean and Panama Canal itineraries.

RelaxAway, Half Moon Cay adds a beach club and villas

RelaxAway, Half Moon Cay is also being expanded ahead of the season. The destination, rebranded from Half Moon Cay in summer 2026, recently added a pier and new amenities through Carnival Cruise Line, Holland America Line’s sister brand.

Additional work includes a new beach club with priority tendering, waiter service, upgraded seating and exclusive food and beverage options. The island is also adding cabanas and villas, expanding shopping and beach facilities, refreshing dining venues including the Lobster Shack, and introducing activities such as pickleball.

Holland America Line will continue offering Caribbean shore excursions developed with The History Channel and “Meet the Makers” tours focused on local artisans and businesses. Additional Oosterdam renovation and voyage details are expected in the coming weeks through the line’s Evolution updates.

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