Holland America Line has announced the opening of its 2027-28 Caribbean season.
Sailing October 2027 through March 2028, the season includes 29 itineraries across 47 departures, 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, deployment and revenue planning for Holland America Line.
The company stated in a press release that the season also introduces enhanced onboard and shoreside experiences, including the debut of the reimagined Oosterdam.
The ship now offers guests new stateroom and suite categories, and Grand Dutch Café, an all-day venue inspired by the company’s Dutch heritage.
During the 2027-28 Caribbean season, the Oosterdam will sail longer itineraries across the Southern Caribbean and Panama Canal.
According to the press release, nearly every itinerary includes a call at RelaxAway, Half Moon Cay.
The destination will provide guests with an elevated experience during the season with a new beach club offering waiter service, priority tendering, exclusive food and beverage options, and upgraded seating.
Guests will also find a refreshed Lobster Shack, island-exclusive menu items and new beverage experiences. Additional upgrades include expanded cabanas and villas, new shopping venues and enhanced beach facilities and activities, such as pickleball.
Shore excursions range from kayaking and snorkeling with stingrays to horseback riding along the beach.
Holland America Line also highlighted that it offers eight holiday cruises during the season.
A highlight sailing of the season is the 28-Day “Pan Am 100th Anniversary Legendary Voyage” aboard the Zuiderdam, departing October 30, 2027, roundtrip from Miami, Florida.
Created in partnership with Pan Am, the sailing traces the airline’s historic Clipper flying boat routes across the Caribbean. The itinerary includes stops in Nassau, Bahamas and San Juan.
Highlighted itineraries include the:
- Five-day Eastern Caribbean & Bahamas Getaway
- Six-day Eastern Caribbean: Amber Cove & Bahamas
- Seven-day Eastern Caribbean: Amber Cove & Key West
- Seven-day Eastern Caribbean: Amber Cove & Bahamas
- Seven-day Eastern Caribbean: San Juan & St. Thomas
- Eight-day Eastern Caribbean: San Juan & St. Thomas
- Nine-, 10- or 11-day Southern Caribbean: ABC Islands
- 10- or 11-day Western Caribbean: Greater Antilles, Belize & Mexico
- 10- or 11-day Eastern Caribbean: Windward & Leeward Islands
- 12-day Panama Canal Discovery: Costa Rica & Greater Antilles, and
- 12-day Eastern Caribbean: Barbados, St. Lucia & St. Kitts.
