Holland America Line has opened its 2027–2028 Caribbean season with a range of short and long cruises designed to give guests more ways to explore the region.
The options range from quick five- and six-day getaways to longer, nine- to 12-day voyages that spend more time in port than any other cruise line sailing the Caribbean. Almost all of the itineraries include a call at RelaxAway, Half Moon Cay, the line’s award-winning private island.
The season includes 29 itineraries across 47 departures from October 2027 to March 2028. The trips will visit 35 ports in 25 countries and territories throughout the Eastern, Western and Southern Caribbean, as well as the Panama Canal. The season also introduces upgraded onboard and shoreside experiences, including the launch of the reimagined Oosterdam as part of the line’s broader Evolution investment across the fleet.
Oosterdam will sail longer itineraries across the Southern Caribbean and Panama Canal. The renewed ship now includes Solo Verandah staterooms with private balconies and dedicated workspace, as well as premium options such as Bridgeview Suites with panoramic ocean views and expanded living space, and Vista Suites. The transformation also adds the Grand Dutch Café.
“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,” Holland America Line vice president of deployment and revenue planning Paul Grigsby said. “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.”
A highlight of the season is the 28-Day Pan Am 100th Anniversary Legendary Voyage aboard Zuiderdam, departing 30 October, 2027, roundtrip from Miami, Florida. The itinerary includes stops in Nassau, Bahamas, and San Juan, two hubs in Pan Am’s Caribbean network, along with ports such as Willemstad, Curaçao; Cartagena; and Colón, Panama.
Holland America Line also offers eight holiday cruises during the season. In the prior month, Holland America Line launched a 2027-2028 season for Europe.
