Key Aspects:
- Holland America Line unveiled its 2027-28 Caribbean season with 47 departures across 29 itineraries.
- The deployment emphasizes longer Caribbean voyages, with more sailings of 9 days or longer.
- The season will also introduce a reimagined Oosterdam and upgrades to RelaxAway, Half Moon Cay.
Longer Caribbean cruises are taking center stage in Holland America Line’s 2027 deployment.
The cruise line has unveiled its 2027-28 Caribbean season, featuring 47 departures across 29 itineraries sailing between October 2027 and March 2028. Cruises range from 5 to 28 days and visit 35 ports in 25 countries throughout the Eastern, Western, and Southern Caribbean.
The longer itineraries will allow ships to reach the Southern Caribbean without sacrificing time in port, giving guests access to less common destinations such as the ABC Islands of Aruba, Bonaire, and Curaçao.
Nearly every itinerary in the new schedule announced on July 6, 2026, will stop at the cruise line’s private island, RelaxAway, Half Moon Cay, in the Bahamas.
Holland America said it will offer more Caribbean cruises lasting 9 days or longer than any other cruise line during the season, giving guests a bigger selection of extended sailings beyond the traditional weeklong cruise.
“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.
Among the offerings are Southern Caribbean cruises to Aruba, Bonaire, and Curaçao and Eastern Caribbean itineraries visiting ports including Puerto Rico, the US Virgin Islands, and St. Maarten.
Western Caribbean voyages will call in Jamaica, Belize, Honduras, and Mexico, with 12-day Panama Canal Discovery sailings including a partial transit of the canal. Those voyages will stop in Colombia, Costa Rica, and the Cayman Islands while allowing guests to experience the locks and Gatun Lake without committing to a full canal crossing or a repositioning voyage.
Holiday travelers will have eight special departures, including Thanksgiving, Christmas, and New Year’s cruises aboard several ships in the fleet.
For those looking for an even longer voyage, the season also includes the cruise line’s Legendary Voyages of longer, destination-intensive sailings that typically feature fewer sea days and multiple consecutive port days or late-evening stays in select ports.
This includes a 28-day Pan Am 100th Anniversary sailing aboard Zuiderdam. Departing October 30, 2027, from Miami, the itinerary visits 19 ports in 13 countries while tracing portions of Pan American Airways’ Caribbean routes.
New Accommodations and Upgrades
Beyond the itinerary lineup, Holland America is introducing several changes that guests will see both onboard and ashore during the 2027 Caribbean season.
The biggest ship upgrade will be the debut of the reimagined Oosterdamwhich will begin sailing Caribbean itineraries in December 2027, following a multi-week dry dock at the Fincantieri shipyard in Palermo, Italy. The vessel will be the first to undergo the cruise line’s Evolution updates designed to refresh accommodations and add new public spaces across existing ships.
The renovations on the 81,769-gross-ton ship will include the addition of Solo Verandah staterooms with private balconies and dedicated workspaces designed for solo passengers. Bridgeview Suites with larger living areas and panoramic ocean views and Vista Suites, which will make their debut on the ship, are also expected.
Meanwhile, RelaxAway, Half Moon Cay will also receive several more upgrades ahead of the season as the cruise line joins other major lines investing heavily in private destinations. The cruise line’s sister company, Carnival Cruise Line, recently added a new pier and amenities to the shared destination.
Next up will be a new beach club that will offer priority tendering, waiter service, upgraded seating, and exclusive food and beverage options. RelaxAway is also adding more cabanas and villas, expanding shopping areas and beach facilities, introducing new activities such as pickleball, updating dining venues, and adding beverage stations across the island. These include Aperol spritz tricycles and Bacardi beach buggies.
During the 2027 season, Holland America Line will continue to offer shore excursions developed with The History Channel alongside its “Meet the Makers” tours, highlighting local artisans and businesses.
Bookings for the 2027-28 Caribbean season are now open with sailings aboard Eurodam, Oosterdam, Rotterdam, Volendam, and Zuiderdam departing primarily from Fort Lauderdale and Miami.
