Holland America Line has unveiled its 2027–2028 Caribbean season with a range of itineraries designed to give guests more ways to explore the region — from quick five- and six-day getaways to longer voyages that spend more time in port than any other cruise line sailing the Caribbean. Nearly every itinerary includes a call at RelaxAway, Half Moon Cay, the line’s award-winning private island.
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.
The season also introduces enhanced onboard and shoreside experiences, including the debut of the reimagined Oosterdam as part of the line’s broader Evolution investment across the fleet.
Paul Grigsby, vice president, deployment and revenue planning for Holland America Line, said: “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.”
And Grigsby continued: “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.”
Throughout the season, guests can expect experiences designed to connect more deeply with the region, both on board and ashore. Shore excursions curated with The HISTORY Channel and locally focused “Meet the Makers” tours bring each destination to life, while Destination Dining and the line’s Global Fresh Fish Program reflect the flavors of the Caribbean. On board, guests can unwind in spaces like the adults-only aft pool, where live music, poolside service and ocean views create a more relaxed atmosphere.
Guests sailing in the Caribbean beginning December 2027 will also have the opportunity to experience the reimagined Oosterdam, the first ship to debut as part of Holland America Line’s Evolution investment. Following its transformation, the ship introduces new stateroom and suite categories designed to reflect how guests travel today, along with expanded access to signature venues.
New accommodations include 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 debuting on the ship for the first time. The transformation also adds Grand Dutch Café, an all-day venue inspired by the line’s Dutch heritage. During the 2027–2028 Caribbean season, Oosterdam will sail longer itineraries across the Southern Caribbean and Panama Canal.
RelaxAway, Half Moon Cay is included on nearly every Caribbean itinerary and is being enhanced with new offerings that elevate the private island experience. A new beach club features waiter service, priority tendering, exclusive food and beverage options, and upgraded seating, along with indoor and outdoor spaces with ship views.
Guests will also find a refreshed Lobster Shack, island-exclusive menu items and new beverage experiences including Aperol spritz tricycles and Bacardi beach buggies. Additional upgrades include expanded cabanas and villas, new shopping venues, 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 offers eight holiday cruises during the season, giving guests a range of options to celebrate at sea. Guests can spend the holidays aboard Rotterdam on a Dec. 22, 2027, roundtrip from Fort Lauderdale, Florida, seven-day Eastern Caribbean Holiday itinerary, sailing to Grand Turk, Turks & Caicos; RelaxAway, Half Moon Cay; Charlotte, Amalie; St. Thomas; and a late-night stay in San Juan, Puerto Rico.
For a longer holiday escape, guests can sail aboard the newly reimagined Oosterdam on an 11-day Southern Caribbean Holiday voyage, also departing Dec. 22, roundtrip from Fort Lauderdale, with calls at RelaxAway, Half Moon Cay; George Town, Grand Cayman; and Cartagena, Colombia, along with late-night stays in Aruba and Curaçao.
A highlight of the season is the 28-Day Pan Am 100th Anniversary Legendary Voyage aboard Zuiderdam, departing Oct. 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, Mexico and Latin America, visiting 19 ports in 13 countries.
Nearly half of the itinerary features destinations that were part of Pan Am’s original network, offering guests the opportunity to follow in the footsteps of one of travel’s most iconic brands while exploring both well-known and less frequently visited ports throughout the region.
Sail on over to www.hollandamerica.com for more.
