Holland America Is Betting Big on Longer Caribbean Cruises, With a New 2027-2028 Season

Holland America Line is doubling down on longer Caribbean voyages for the 2027-2028 cruise season, unveiling a schedule heavy on extended itineraries, more port time and a revamped flagship experience centered on the region.

The new deployment includes 29 itineraries across 47 departures between October 2027 and March 2028, spanning everything from five-day Bahamas escapes to a 28-day voyage inspired by the historic Pan Am flying boat routes. The line says it will offer more Caribbean cruises of nine days or longer than any other cruise line during the season.

The program covers 35 ports in 25 countries and territories across the Eastern, Western and Southern Caribbean, along with Panama Canal sailings.

A central part of the season remains RelaxAway, Half Moon Cay, Holland America’s private island in The Bahamas, with nearly every itinerary including a call there.

The private destination is also getting a series of enhancements 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 facilities and activities like pickleball.

The cruise line is also emphasizing destination-focused experiences ashore, including HISTORY Channel-themed excursions, locally focused “Meet the Makers” tours and Caribbean-inspired dining programs on board.

A New Look for Oosterdam

One of the biggest additions to the season is the Caribbean debut of the newly reimagined Oosterdam, the first vessel to emerge from Holland America’s broader fleet modernization program.

Beginning in December 2027, the ship will sail longer Southern Caribbean and Panama Canal itineraries after a transformation that includes new accommodation categories, including Solo Verandah staterooms, Bridgeview Suites and Vista Suites.

The renovation also adds the Grand Dutch Café, one of the brand’s signature venues.

Longer Caribbean Voyages

While the schedule includes shorter five- and six-day sailings from Fort Lauderdale, the emphasis is clearly on week-plus cruises.

Highlights include nine-, 10- and 11-day Southern Caribbean voyages visiting Aruba, Curaçao and Bonaire; longer Eastern Caribbean sailings featuring islands like Antigua, Martinique, St. Kitts, Dominica and St. Lucia; Western Caribbean cruises calling in Jamaica, Belize, Honduras and Mexico; and 12-day Panama Canal itineraries that include a partial canal transit.

Holiday departures are also returning, with Christmas sailings featuring destinations including Grand Turk, St. Thomas, San Juan, Aruba, Curaçao and Grand Cayman.

A Pan Am-Themed Voyage

Among the season’s most distinctive sailings is a 28-day Pan Am 100th Anniversary Legendary Voyage aboard Zuiderdam.

Departing from Miami on Oct. 30, 2027, the itinerary was developed in partnership with Pan Am and follows many of the airline’s historic Caribbean and Latin American flying boat routes.

The voyage visits 19 ports in 13 countries, including Nassau, San Juan, Curaçao, Cartagena and Colón, combining classic Caribbean ports with a number of less frequently visited destinations.

Growing Demand for Longer 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.

Those extended voyages typically allow ships to include deeper Southern Caribbean itineraries, Panama Canal sailings and more overnight or late-evening calls while appealing to travelers looking to spend more time in destinations rather than at sea.

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