Holland America Line has announced its 2027–2028 Caribbean season, offering 29 itineraries across 47 departures from October 2027 through March 2028. The season includes quick five- and six-day getaways as well as longer voyages, with more nine-day-or-longer itineraries than any other cruise line, according to the company. Nearly every sailing calls at RelaxAway, Half Moon Cay, the line's award-winning private island.
Itineraries and Destinations
The season visits 35 ports in 25 countries and territories throughout the Eastern, Western and Southern Caribbean, as well as the Panama Canal. Highlights include a 28-day Pan Am Legendary Voyage that traces historic Clipper flying boat routes. Shorter options range from five-day escapes to longer journeys that spend more time in port.
“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. “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.”
Enhanced Onboard and Shoreside Experiences
Guests can enjoy shore excursions curated with The HISTORY Channel and locally focused “Meet the Makers” tours. Destination Dining™ and the Global Fresh Fish Program bring Caribbean flavors to the table. On board, the adults-only aft pool offers live music, poolside service, and ocean views.
Beginning December 2027, the reimagined Oosterdam debuts as part of the line’s Evolution investment. New accommodations include Solo Verandah staterooms with private balconies, Bridgeview Suites with panoramic views, and Vista Suites for the first time on this ship. The transformation also adds Grand Dutch Café, an all-day venue inspired by Dutch heritage. Oosterdam will sail longer itineraries across the Southern Caribbean and Panama Canal during the season.
Private Island and Signature Experiences
RelaxAway, Half Moon Cay remains a centerpiece, featured on nearly every itinerary. The island offers pristine beaches, water activities, and cabanas. Combined with upgraded fleet amenities, the season aims to provide immersive Caribbean experiences both ashore and at sea.
