by Sarah Kuta
Last updated: 10:50 AM ET, Mon July 6, 2026
Holland America Line is unveiling its 2027-2028 Caribbean season.
From October 2027 through March 2028, the company will offer 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. Nearly every itinerary includes a call at RelaxAway, Half Moon Cay, the line’s award-winning private island.
“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,” says Paul Grigsby, vice president, deployment and revenue planning for Holland America Line. “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.”
The season also introduces enhanced onboard and shoreside experiences, including shore excursions curated with The HISTORY Channel and locally focused “Meet the Makers” tours bring each destination to life. 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.
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.
A highlight of the season is the 28-day Pan Am 100th Anniversary Legendary Voyage aboard 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, Mexico and Latin America, visiting 19 ports in 13 countries.
Holland America Line is also offering eight holiday cruises during the season. Ships are decorated for the season and feature festive dining, live music and holiday programming that bring together traditions from around the world, giving guests the opportunity to celebrate without the stress of planning.
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