Holland America Line is doubling its longer Caribbean sailings for the 2027-2028 cruise season, unveiling longer itineraries, more port times and improved flagship experiences centered on the region.
The new distribution includes: 47 departure points, 29 itineraries From October 2027 to March 2028, they cover everything from a five-day Bahamas escape to a 28-day voyage inspired by the historic Pan Am airship route. The line says it will make an offer. More nine-day or longer Caribbean cruises than any other cruise line. During the season.
The program is as follows 35 ports in 25 countries and regions Cross the Eastern, Western and Southern Caribbean with a Panama Canal sailing.
The central part of the season remains. Relaxaway, Half Moon KHolland America’s private island in the Bahamas has almost every itinerary that includes a visit there.
The private destination is also making a series of improvements ahead of the season, including a new beach club with waiter service, upgraded cabanas and villas, expanded food and beverage options, new shopping, additional beach amenities and activities like pickleball.
The cruise line is also emphasizing destination-focused shore experiences, including HISTORY Channel themed excursions, regionally focused “Meet the Makers” tours and Caribbean-inspired onboard dining programs.
A new look at Oosterdam
One of the biggest additions this season is the newly reimagined Caribbean debut. OosterdamIt is the first ship to emerge from Holland America’s extensive fleet modernization program.
Beginning in December 2027, the ship will undergo a refit that includes new accommodation categories including Solo Verandah staterooms, Bridgeview Suites and Vista Suites, and will sail longer Southern Caribbean and Panama Canal itineraries.
The renovation also added the Grand Dutch Café, one of the brand’s signature locations.
Longer Caribbean Voyages
The itineraries include shorter five- and six-day sailings from Fort Lauderdale, but the focus is clearly on cruises of a week or longer.
Highlights include 9-, 10- and 11-day Southern Caribbean sailings visiting Aruba, Curaçao and Bonaire. longer Eastern Caribbean voyages featuring islands such as Antigua, Martinique, St. Kitts, Dominica, and St. Lucia; Western Caribbean cruises visiting Jamaica, Belize, Honduras, and Mexico; A 12-day Panama Canal itinerary that includes partial canal transit.
Holiday departures are also back with Christmas sailings featuring destinations including Grand Turk, St. Thomas, San Juan, Aruba, Curaçao and Grand Cayman.
Pan Am themed sailing
Among the most unique sailings of the season: 28-day Pan Am 100th anniversary legendary voyage aboard Jawi the dam.
Departing from Miami on October 30, 2027, the itinerary was developed in partnership with Pan Am and follows the airline’s historic Caribbean and Latin American airship routes.
sailing visit 19 ports in 13 countriesIt combines classic Caribbean ports with several less frequently visited destinations, including Nassau, San Juan, Curaçao, Cartagena, and Colón.
Growing demand for long-haul Caribbean cruises
The announcement reflects a broader trend across the Caribbean cruise industry, where cruise lines are increasingly expanding longer itineraries beyond the traditional seven-day format.
These extended voyages allow ships to typically include deeper southern Caribbean itineraries, Panama Canal sailings, and more overnight or late evening calls, appealing to travelers who want to spend more time at the destination rather than at sea.
