Holland America Line has unveiled its 2027–2028 Caribbean season, featuring 47 departures across 29 itineraries ranging from five-day escapes to extended voyages through the Caribbean and Panama Canal.
Sailing between October 2027 and March 2028, the program visits 35 ports across 25 countries and territories, with nearly every itinerary including a call at the line’s private island, RelaxAway, Half Moon Cay.
Longer stays and more destination immersion
The new season has been designed to give guests more time ashore, with Holland America Line continuing its focus on destination-rich itineraries.
Guests can choose from Eastern, Western and Southern Caribbean sailings, as well as Panama Canal voyages, with onboard experiences complemented by Destination Dining, the Global Fresh Fish Program, HISTORY Channel shore excursions and locally focused “Meet the Makers” experiences.
Paul Grigsby, Vice President of Deployment and Revenue Planning for Holland America Line, said the new season caters to a wide range of travellers.
“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,” he said.
Reimagined Oosterdam joins the fleet
A highlight of the season will be the Caribbean debut of the newly refurbished Oosterdam following its Evolution transformation.
The refreshed ship will introduce new accommodation categories, including Solo Verandah staterooms, Bridgeview Suites and Vista Suites, alongside the addition of the Grand Dutch Café. Oosterdam will operate longer Southern Caribbean and Panama Canal itineraries during the season.
Private island enhancements
RelaxAway, Half Moon Cay is also receiving a series of upgrades ahead of the season, including a new beach club, expanded cabanas and villas, refreshed dining venues, new beverage experiences and additional recreational activities.
The season also includes eight festive holiday sailings and a 28-day Pan Am 100th Anniversary Legendary Voyage aboard Zuiderdam, retracing the historic flying boat routes of Pan American Airways through the Caribbean and Latin America.
Guests booking eligible 2027–2028 Caribbean cruises with the Have It All package will receive inclusions such as shore excursions, specialty dining, a Signature Beverage Package and Wi-Fi.
