Holland America Opens 2027-28 Caribbean Season With Longer Routes

Updated July 7, 2026

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, whether they are looking for a quick getaway or a longer journey that explores more of the region," said Paul Grigsby, vice president, deployment and revenue planning for Holland America Line. "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 and with signature experiences on board."

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 call in Jamaica, Belize, Honduras and Mexico.

The season also includes 12-day Panama Canal Discovery cruises with a partial transit of the canal, taking in 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.

Holiday options include Rotterdam's seven-day Eastern Caribbean Holiday itinerary departing Dec. 22, 2027, roundtrip from Fort Lauderdale, with calls at Grand Turk, RelaxAway, Half Moon Cay, Charlotte Amalie, St. Thomas, and a late-night stay in San Juan. Oosterdam is also scheduled to depart Dec. 22 on an 11-day Southern Caribbean Holiday voyage roundtrip from Fort Lauderdale, calling at RelaxAway, Half Moon Cay, George Town and Cartagena, with late-night stays in Aruba and Curacao. Ships will be decorated for the season, Holland America Line said, with festive dining, live music and holiday programming.

Across the program, Holland America Line will continue offering Caribbean shore excursions developed with The History Channel, along with "Meet the Makers" tours focused on local artisans and businesses. The line also said Destination Dining and its Global Fresh Fish Program will lean into Caribbean flavors, while onboard spaces such as the adults-only aft pool will offer live music, poolside service and ocean views.

The longest Caribbean offering is a 28-day sailing, the 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 Clipper flying boat routes across the Caribbean, Mexico and Latin America. Nearly half of the itinerary features destinations from Pan Am's original network, Holland America Line said, including Nassau and San Juan, along with calls such as Willemstad, Cartagena and Colon. The voyage also includes multiple consecutive port days in parts of the Caribbean.

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 have not been finalized, and the work is focused on interiors, venues and cabin categories. No ship lengthening or additional decks are planned.

Oosterdam's changes will include Solo Verandah staterooms with private balconies and dedicated workspaces, along with Bridgeview Suites offering panoramic ocean views and expanded living space. Vista Suites will debut on the ship, and the transformation will add the Grand Dutch Café, an all-day venue inspired by Holland America Line's Dutch heritage. During the season, Oosterdam 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, exclusive food and beverage options, and indoor and outdoor spaces with ship views. The island is also adding expanded cabanas and villas, new shopping venues and enhanced beach facilities.

Dining and beverage additions include a refreshed Lobster Shack, island-exclusive menu items, Aperol spritz tricycles and Bacardi beach buggies. New activities include pickleball. Shore excursions range from kayaking and snorkeling with stingrays to horseback riding along the beach.

Additional Oosterdam renovation and voyage details are expected in the coming weeks through the line's Evolution updates.

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