Holland America Line has opened bookings for its 2027-2028 Caribbean season, offering a wide range of itineraries designed to provide more ways to discover 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, running from October 2027 to March 2028, comprises 29 itineraries across 47 sailings, visiting 35 ports in 25 countries and territories of the Eastern, Western, and Southern Caribbean, as well as the Panama Canal. It also features new experiences both onboard and ashore, including the debut of the refurbished Oosterdam, part of the Evolution modernization program 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 voyage that allows them to explore the region in depth,” said Paul Grigsby, Vice President of Rollout Planning and Revenue for Holland America Line. “By offering more Caribbean itineraries of nine days or more than any other cruise line, our guests have more time to experience each destination and enjoy both our private island and exclusive onboard experiences.”
Throughout the season, travelers can enjoy experiences designed to connect them with the essence of the Caribbean both on board and ashore. Excursions, developed in collaboration with The HISTORY Channel, and Meet the Makers tours, focused on local producers and artisans, will provide an intimate look at each destination. The culinary offerings, featuring Destination Dining™ and the Global Fresh Fish program, will showcase the flavors of the Caribbean. In addition, passengers can relax in spaces such as the exclusive adults-only aft pool, complete with live music, poolside service, and ocean views.
From December 2027, those sailing through the Caribbean will be able to discover the revamped Oosterdam, the first ship to debut after its transformation within the Evolution program.
The ship will incorporate new categories of cabins and suites adapted to the current needs of travelers, including single cabins with private balcony and workspace, as well as new Bridgeview Suites, with panoramic ocean views and larger area, and the Vista Suites, which are being launched for the first time on this ship.
The Grand Dutch Café, inspired by the cruise line's Dutch heritage, will also be added to the dining options. During the 2027-2028 Caribbean season, the Oosterdam will primarily operate extended itineraries in the Southern Caribbean and through the Panama Canal.
RelaxAway's private island, Half Moon Cay, included in virtually all Caribbean itineraries, will debut new offerings to enhance the traveler experience. Among the new features are a new beach club with waiter service, priority disembarkation, an exclusive food and beverage selection, indoor and outdoor areas with views of the ship, and improved relaxation spaces.
The Lobster Shack will also be renovated, and new island-exclusive dishes and experiences like Aperol Spritz tricycles and Bacardi Beach Buggies will be added. Improvements also include new cabanas and villas, retail spaces, updated beach facilities, and activities such as pickleball. Excursions will offer kayaking, snorkeling with stingrays, and horseback riding on the beach.
Christmas celebrations at sea
The season will feature eight special Christmas and New Year's cruises. Among them is a seven-day Eastern Caribbean itinerary aboard the Rotterdam, departing on December 22, 2027, from Fort Lauderdale, with stops in Grand Turk, RelaxAway Half Moon Cay, Charlotte Amalie (St. Thomas), and San Juan, where it will remain until late into the night.
Those seeking a longer Christmas vacation can embark on the revamped Oosterdam for an 11-day Southern Caribbean cruise, also departing December 22 from Fort Lauderdale, which will visit RelaxAway Half Moon Cay, George Town (Grand Cayman), Cartagena and offer 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 from Miami on October 30, 2027. Developed in partnership with Pan Am, this commemorative itinerary follows the historic routes of the Clipper flying boats, exploring the Caribbean, Mexico, and Latin America, and visiting 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 travel history.
The tour includes stops in Nassau, San Juan, Willemstad (Curacao), Cartagena and Colón (Panama), plus several consecutive days in port to enjoy a much more immersive experience than traditional cruises.
Main routes
Five and six day getaways
- Eastern Caribbean and Bahamas (5 days) – Zuiderdam
Departure and return to Fort Lauderdale (December 18, 2027). Stopovers in Nassau, RelaxAway Half Moon Cay and Grand Turk. - Eastern Caribbean: Amber Cove and Bahamas (6 days) – Eurodam
Departure and return to Fort Lauderdale (March 26, 2028). Stopovers at RelaxAway Half Moon Cay, Amber Cove (Dominican Republic) and Grand Turk.
Seven and eight day itineraries
- They include routes through the Eastern Caribbean with stops in Amber Cove, Key West, San Juan, St. Thomas, St. Maarten and the Bahamas, aboard Eurodam, Rotterdam and Zuiderdam, with departures between October 2027 and March 2028.
Itineraries of nine to twelve days
- The offer includes tours of the Southern Caribbean (Aruba, Bonaire and Curacao), the Western Caribbean (Jamaica, Belize and Mexico), the Windward and Leeward Islands, as well as several 12-day cruises through the Panama Canal, with partial transit through the canal and navigation on Gatun Lake.
- A 12-day Eastern Caribbean itinerary is also offered, with stops in Barbados, St. Lucia, Martinique, St. Kitts, Tobago and St. Maarten, aboard the Volendam.
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