Holland America Line has opened bookings for its 2027–2028 Caribbean season, featuring a wide range of itineraries designed to offer more ways to explore the region: from five- and six-day getaways to extended cruises that spend more time in each port than any other cruise line operating in the Caribbean. Nearly all itineraries include a stop at RelaxAway, Half Moon Cay, the company’s private island.
The season, which will run from October 2027 to March 2028, includes 29 itineraries spread across 47 sailings, with stops at 35 ports in 25 countries and territories in the Eastern, Western, and Southern Caribbean, as well as the Panama Canal. In addition, it features new experiences both on board and ashore, including the debut of the refurbished Oosterdam as part of the Evolution modernization program, which is being implemented across the entire fleet.
“We’ve designed this season to offer our guests more ways to discover the Caribbean, whether they’re looking for a short getaway or a longer trip that allows them to explore the region in depth,” says Paul Grigsby, vice president of deployment and revenue planning at Holland America Line. “By offering more Caribbean itineraries of nine days or longer than any other cruise line, our guests have more time to get to know each destination and enjoy both our private island and exclusive onboard experiences.”
Throughout the season, travelers will be able to enjoy experiences designed to connect them with the essence of the Caribbean, both on board and ashore. The excursions—developed in collaboration with The HISTORY Channel—and the “Meet the Makers” tours, which focus on local producers and artisans, will offer an up-close look at each destination. The culinary offerings, featuring Destination Dining™ and the Global Fresh Fish program, will highlight the flavors of the Caribbean. In addition, passengers can relax in areas such as the adults-only aft pool, complete with live music, poolside service, and ocean views.
Starting in December 2027, travelers cruising the Caribbean will be able to experience the refurbished Oosterdam, the first ship to debut following its transformation as part of the Evolution program.
The ship will feature new categories of staterooms and suites tailored to the current needs of travelers, including single staterooms with private balconies and workspaces, as well as new Bridgeview Suites—which offer panoramic ocean views and more space—and Vista Suites, which are making their debut on this ship.
In addition, the Grand Dutch Café, inspired by the Dutch seafaring tradition, will become part of the dining options. During the 2027–2028 Caribbean season, the Oosterdam will primarily operate extended itineraries through the Southern Caribbean and the Panama Canal.
RelaxAway’s private island, Half Moon Cay—which is included in virtually all Caribbean itineraries—will debut new offerings to enhance the traveler experience. Highlights include a new beach club with waitstaff, priority disembarkation, an exclusive food and beverage menu, indoor and outdoor areas with views of the ship, and improved relaxation areas.
The Lobster Shack will also be renovated, and new dishes exclusive to the island will be introduced, along with experiences such as Aperol Spritz tricycles and Bacardi Beach Buggies. The improvements also include new cabanas and villas, retail spaces, renovated beach facilities, and activities such as pickleball. Excursions will include kayaking, snorkeling with stingrays, and horseback riding on the beach.
Christmas Celebrations on the High Seas
The season will feature eight special Christmas and New Year's cruises. Among them is a seven-day itinerary through the Eastern Caribbean aboard the Rotterdam, departing on December 22, 2027, from Fort Lauderdale and making stops at Grand Turk, RelaxAway Half Moon Cay, Charlotte Amalie (St. Thomas), and San Juan, where it will remain until late at night.
Those looking for a longer Christmas vacation can board the refurbished Oosterdam for an 11-day cruise through the Southern Caribbean, also departing on December 22 from Fort Lauderdale. The cruise will visit RelaxAway Half Moon Cay, George Town (Grand Cayman), and Cartagena, and will include overnight stops in Aruba and Curaçao.
All the ships will be decorated for the holidays and will offer special menus, live music, and activities inspired by Christmas traditions from around the world.
One of the season’s highlights will be the Pan Am 100th Anniversary Legendary Voyage, a 28-day cruise aboard the Zuiderdam, departing on October 30, 2027, from Miami. Developed in collaboration with Pan Am, this commemorative itinerary follows the historic routes of the Clipper seaplanes, traveling through the Caribbean, Mexico, and Latin America and calling at 19 ports in 13 countries. Nearly half of the ports of call were part of Pan Am’s original network, offering travelers the chance to relive one of the most iconic eras in the history of travel.
The itinerary includes stops in Nassau, San Juan, Willemstad (Curaçao), Cartagena, and Colón (Panama), as well as several consecutive days in port to enjoy a much more immersive experience than that of traditional cruises.
Main Routes
Five- and six-day getaways
- Eastern Caribbean and the Bahamas (5 days) – Zuiderdam
Departure from and return to Fort Lauderdale (December 18, 2027). Port calls in Nassau, RelaxAway Half Moon Cay, and Grand Turk. - Eastern Caribbean: Amber Cove and the Bahamas (6 days) – Eurodam
Departure from and return to Fort Lauderdale (March 26, 2028). Port calls at RelaxAway Half Moon Cay, Amber Cove (Dominican Republic), and Grand Turk.
Seven- and eight-day itineraries
- They include itineraries through the Eastern Caribbean with stops in Amber Cove, Key West, San Juan, St. Thomas, St. Maarten, and the Bahamas, aboard the Eurodam, Rotterdam, and Zuiderdam, with departures between October 2027 and March 2028.
Nine- to twelve-day itineraries
- The offerings include cruises through the Southern Caribbean (Aruba, Bonaire, and Curaçao), the Western Caribbean (Jamaica, Belize, and Mexico), the Windward and Leeward Islands, as well as several 12-day cruises through the Panama Canal, featuring a partial transit through the canal and a cruise on Gatún Lake.
- A 12-day itinerary through the Eastern Caribbean is also available, with stops in Barbados, Saint Lucia, Martinique, Saint Kitts, Tobago, and St. Maarten, aboard the Volendam.
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