Holland America Opens Bookings for 2027-28 Caribbean Season

Holland America's cruise ship Oosterdam in port
Cruise Industry The Caribbean
by Sam Hamilton

Holland America Line has unveiled its 2027-28 Caribbean cruise program, featuring a wide range of itineraries across the region.

Running from October 2027 through March 2028, the season includes 47 departures across 29 itineraries, visiting 35 ports in 25 countries and territories throughout the Eastern, Western, and Southern Caribbean, as well as the Panama Canal.

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 of Deployment and Revenue Planning for Holland America Line.

According to the cruise line, the new season also introduces enhanced onboard and destination experiences, including the debut of the newly refreshed *Oosterdam *which will feature new stateroom and suite categories, along with the Grand Dutch Café, an all-day dining venue inspired by Holland America Line’s Dutch heritage.

Throughout the Caribbean season, *Oosterdam *will operate longer voyages exploring the Southern Caribbean and transiting the Panama Canal.

Holland America also said that almost every itinerary will include a visit to RelaxAway, Half Moon Cay, where guests can enjoy a number of new enhancements. The private destination will introduce a new beach club offering waiter service, priority tender access, exclusive food and beverage selections, and upgraded seating options.

Visitors will also find a redesigned Lobster Shack, island-only menu offerings, new beverage experiences, expanded cabanas and villas, additional shopping outlets, and upgraded beach amenities, including pickleball courts. Available shore excursions include activities such as kayaking, snorkeling with stingrays, and horseback riding along the beach.

The cruise line also highlighted eight holiday sailings scheduled during the season.

One of the standout voyages is the 28-Day “Pan Am 100th Anniversary Legendary Voyage” aboard Zuiderdam, departing roundtrip from Miami on October 30, 2027. Developed in partnership with Pan Am, the cruise follows the historic routes of the airline’s famous Clipper flying boats through the Caribbean, with ports of call including Nassau in the Bahamas and San Juan, Puerto Rico.

**Featured itineraries for the 2027-28 season include: **

  • Five-day Eastern Caribbean & Bahamas Getaway
  • Six-day Eastern Caribbean: Amber Cove & Bahamas
  • Seven-day Eastern Caribbean: San Juan & St. Thomas
  • Seven-day Eastern Caribbean: Amber Cove & Key West
  • Seven-day Eastern Caribbean: Amber Cove & Bahamas
  • Eight-day Eastern Caribbean: San Juan & St. Thomas
  • Nine-, 10-, and 11-day Southern Caribbean: ABC Islands
  • 10- and 11-day Eastern Caribbean: Windward & Leeward Islands
  • 10- and 11-day Western Caribbean: Greater Antilles, Belize & Mexico
  • 12-day Panama Canal Discovery: Costa Rica & Greater Antilles
  • 12-day Eastern Caribbean: Barbados, St. Lucia & St. Kitts