Holland America Line has officially opened bookings for its 2027-2028 Caribbean cruise season, running from October 2027 through March 2028.
The programmer offers 29 itineraries across 47 departures from October 2027 to March 2028. Options range from short five- and six-day breaks to longer voyages with extended port time. Nearly every sailing includes the private island RelaxAway at Half Moon Cay, with visits to 35 ports across 25 countries and territories. Enhanced experiences include HISTORY Channel excursions, local tours and the reimagined Oosterdam ship featuring new staterooms and venues.
The upcoming season covers the Eastern, Western, and Southern Caribbean regions, as well as transit options through the Panama Canal. Cruisers will visit 35 ports across 25 different countries and territories. Ships like Rotterdam, Zuiderdam, and Eurodam will operate key routes out of major Florida hubs like Miami and Fort Lauderdale. Maintaining its reputation for deeper regional travel, the line is offering more Caribbean itineraries of 9 to 12 days or longer than any other competing cruise line.
Breaking from tradition, the line is testing select 5- and 6-day short escapes out of Fort Lauderdale for travelers seeking quicker getaways.
A focal point of the 2027-2028 season is the Caribbean debut of the upgraded Oosterdam ship following its fleet-modernization “Evolution” refit. The ship adds 30 dedicated Solo Verandah staterooms featuring private balconies and specialized workspaces to accommodate the growing solo travel market. The design introduces new Bridgeview Suites offering panoramic ocean views and updated Vista Suites.
The ship will now feature the Grand Dutch Café, an all-day dining venue celebrating the
Oosterdam will specifically handle the longer itineraries across the Southern Caribbean and the Panama Canal. Nearly every itinerary on the schedule includes a dedicated stop at RelaxAway, Half Moon Cay, Holland America’s award-winning private island destination in the Bahamas.
The island is debuting significant infrastructure enhancements for this season. Upgraded amenities include a new beach club with personalised waiter service, priority tendering access, and exclusive premium dining layouts. Refreshed food stands include the Lobster Shack, Aperol Spritz mobile tricycles, and freshly constructed pickleball courts.
For aviation and history enthusiasts, the crown jewel of the season is the 28-Day Pan Am 100th Anniversary Legendary Voyage aboard the Zuiderdam. The departure sails roundtrip from Miami, Florida on October 30, 2027. Developed in partnership with Pan Am, this unique voyage traces the historical routes of the company’s famous Clipper flying boats. The ship will call on 19 ports across 13 countries, featuring consecutive port days in historic early network hubs like San Juan, Puerto Rico, and Nassau, Bahamas. While Foynes, County Limerick, is a legendary landmark in aviation history, serving as a crucial transatlantic base for Pan Am’s Boeing 314 Clippers, it is not part of this specific cruise because the ship does not cross the Atlantic Ocean
The line has confirmed eight special holiday cruises encompassing Thanksgiving, Christmas, and New Year itineraries. These specific sailings feature distinct international holiday programming, worldwide culinary menus, and festive decor to ensure hassle-free holiday hosting at sea. Bookings are actively open to the public on the Holland America Line Site.
