Holland America Line and Pan Am Partner for 28-Day ‘Golden Age’ Anniversary Cruise

In an era when modern air travel is often defined headaches and hurry, two heritage brands are teaming up to bring back the romance, style, and deliberate pace of mid-century travel.

Holland America Line (HAL) and Pan American Global Holdings revealed new details this week onboard Volendam at the Manhattan Cruise Terminal for their upcoming Pan Am 100th Anniversary Legendary Voyage—a 28-day Caribbean and Central American itinerary aboard Zuiderdam set to depart roundtrip from Miami on Oct. 30, 2027.

The voyage, on sale now still with availability, marks the centennial of Pan American World Airways, which launched its first airmail flight out of Florida to Havana in October 1927.

Speaking at a media launch event aboard Volendam on Thursday, Paul Grigsby, vice president of itinerary planning and deployment for Holland America Line, and Craig Carter, CEO of Pan American Global Holdings, detailed how the collaboration came together and why travelers are hungering for a return to the “Golden Age” of travel.

Island Hopping by Sea and Sky

The idea for the collaboration originated when Grigsby was reading Stranded in the Sky: The Untold Story of Pan Am Luxury Airliners Trapped on the Day of Infamy, and evaluating the early days of Pan Am’s transpacific and Caribbean operations, where early “Flying Clippers” had limited range and had to leapfrog between island outposts.

“These aircraft had relatively small ranges—like 2,500 to 3,000 miles—and in order to get across the Pacific, they would have to leapfrog and do basically stepping stones across the sea,” Grigsby said on Thursday. “It dawned on me that that’s a lot like how we design cruises. We don’t have a problem with range, but we add all of those stepping stones for enrichment. That’s what people want to do—they want to collect these various places.”

Grigsby mapped out a 28-day route following Pan Am’s historic “Great Circle” route through the Caribbean—a region where Pan Am founder Juan Trippe first built the airline’s network. The itinerary features 13 of the 16 countries originally served by the Flying Clippers, along with strategic historical ports like Curaçao, which served as a crucial refueling stop for the flying boats during World War II.

While a 28-day Caribbean cruise is rare in an industry dominated by three- to seven-night runs, HAL leadership embraced the scope.

“I think Holland America is one of the few companies that would be audacious enough to do a 28-day Caribbean cruise,” Grigsby noted. “What we’re celebrating with this cruise is kind of this rare intersection of air and sea, when flying boats looked a lot like ships.”

For Pan Am, the partnership felt like a natural fit for two brands that shaped 20th-century global mobility.

“One in 10 people who immigrated from Europe in the early 1900s came in on a Holland America Line ship,” Carter said. “You go to the ’50s, ’60s, and ’70s, and you talk to a lot of people that immigrated… they came in on a Pan Am plane. The nostalgia and history between our two brands together is very formidable.”

Onboard Experience: Menus, Memorabilia, and Clipper Clubs

On board Zuiderdam, the 28-day sailing will act as a “seagoing time capsule,” featuring retrofitted spaces, vintage dining, and specialized enrichment:

• Recreated Clipper Club: The ship will feature moments inspired by Pan Am’s famous Clipper Club—the airline’s exclusive network of airport lounges that pioneered luxury pre-flight hospitality.
  
• Period Culinary & Cocktails: Menus will feature reimagined classic dishes served during Pan Am’s peak years, including Cocktail de Crevettes, Sole en Croûte (Dover sole with crabmeat filling in puff pastry), and Soufflé Grand Marnier. The bar program will feature historical cocktails like the Pan Am Cocktail (white rum, Campari, orgeat, lemon, and egg white) and the classic Clipper Cocktail (Mount Gay Eclipse rum, Dolin Blanc, and grenadine).
  
• Guest Speakers & Historians: Presentations will feature aviation historians and storytellers, including actor Willie Aames (Eight Is Enough, Charles in Charge); Linda Freire and David Hinson of the Pan Am Museum Foundation; international speaker Steve Gray; and hospitality executive and multi-million-miler pilot David Kliman.

On shore, HAL has created exclusive shore excursions tracing Pan Am’s operational footprint. Highlights include classic roadster tours in Cartagena, Colombia; visits to the Chaguaramas flying boat base in Trinidad; navigation tours to Shirley Heights in Antigua; and excursions along the Panama Canal Railway in Colón.

A One-Off Voyage—For Now

While current plans call for the October 2027 voyage to be a special single-sailing event, both executives hinted that future collaborations aren’t out of the question if passenger demand holds.

When asked if the concept could expand beyond 2027, Grigsby pointed to other famous aviation paths. “The Pacific route would be super fun to recreate—either the China Clipper or the Anzac Clipper that operated from San Francisco down to the Pacific,” Grigsby said, referencing historic routes that island-hopped through Kiribati, Samoa, New Caledonia, and New Zealand.

For now, the focus remains on the 2027 centennial departure out of Miami.

“If you’re a history buff, you love aviation, and you love cruising, this is the journey that you want to be on,” Carter said.