Holland America Line Tests Short Cruises with 2027/28 Caribbean Season

While Holland America Line is better known for its longer cruise options, for the 2027/28 Caribbean cruise season, the line is testing out two short cruise itineraries of five- and six-days, respectively. Nearly every sailing in the region will stop at RelaxAway, Half Moon Cay.

Sailing October 2027 through March 2028, the full 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.  

Holland America will offer eight holiday cruises during the season, ranging from seven to 11 days.

“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.

Short Itineraries

Holland America will offer two short Caribbean cruises during the 2027/28 season. The first is a five-day Eastern Caribbean & Bahamas getaway that sails roundtrip from Fort Lauderdale to Nassau, RelaxAway Half Moon Cay, and Grand Turk, departing Dec. 18, 2027.

The second is a six-day Eastern Caribbean cruise, sailing roundtrip from Fort Lauderdale and visiting RelaxAway Half Moon Cay, Amber Cover, and Grand Turk, departing March 26, 2028.

Oosterdam’s First Caribbean Season Post-Refurb, RelaxAway Half Moon Cay Improvements

The 2027/28 season also marks a new chapter for Oosterdam in the Caribbean. Beginning December 2027, the ship – which was the first ship in the HAL fleet to undergo an Evolution refurbishment, in April 2025 – will make its first appearance in the Caribbean since the refit. During the 2027/28 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 includes a new beach club with 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.

Pan Am 100th Anniversary Legendary Voyage

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.

The itinerary includes stops in Nassau, Bahamas, and San Juan, two early hubs in Pan Am’s Caribbean network, along with ports such as Willemstad, Curaçao; Cartagena; and Colón, Panama. The voyage also includes multiple consecutive port days in parts of the Caribbean, giving guests more time in the destination compared to shorter itineraries.

Longer Caribbean Cruise Itineraries

While, the bulk of the 2027/28 season will be seven-day cruise options, HAL will also offer nine- to 12-day options, including nine, 10-, or 11-day Southern Caribbean ABC Island cruises; 10- and 11-day Western and Eastern Caribbean sailings; 12-day Panama Canal Discovery cruises; and a 12-day Eastern Caribbean option.

“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,” Grigsby said.