New cruise to retrace Pan Am Clipper's route in the Caribbean and Latin America

Nostalgia for a South Florida-born aviation pioneer has reached the high seas.

Cruise line Holland America and Pan American World Airways are teaming up to offer a 28-day cruise to the Caribbean and Latin America that retraces the original flying Clipper routes.

The voyage, which takes place during Pan Am’s 100th anniversary, will depart PortMiami on Oct. 30, 2027, and return there the following month, both companies told the Miami Herald on Monday.

With 18 ports of call, the Holland Zuiderdam will first head south to Jamaica, then east to Puerto Rico, southwest to Colombia, and finally return to Miami via stops in Panama and Mexico. During one stretch, the ship will make six ports of call in six days.

Holland, owned by Doral-based Carnival, is calling the cruise the 28-Day Pan Am 100th Anniversary Legendary Voyage.

Pan Am nostalgia

The trip serves as a reminder of the strong ties some in South Florida have for the former airline, which filed for bankruptcy protection in January 1991 and by the end of that year shut down operations.

Pan Am was founded in 1927 as the first international airline in the U.S., initially in Key West. In 1928, the airline opened a terminal and airfield on Northwest 36th Street on the site of the original Miami International Airport. Several of its buildings there remain intact.

The idea for the cruise came when a Holland executive read the book "Stranded in the Sky: The Untold Story of Pan Am Luxury Airliners Trapped on the Day of Infamy," by Phillip Jett. The work chronicles Pan Am’s predicament during the bombing of Pearl Harbor and the flying boat service the carrier had in the Pacific.

"The genesis really came from reading the book," Paul Grigsby, vice president of itinerary planning and deployment for Holland America Line, said in an interview with the Miami Herald. "It got me thinking about the service network that they created" in that era and at that delicate time.

Then, about a year ago, Grigsby contacted Pan American World Airways, the company that owns the branding and logos of the long-bankrupt airline.

"I got a pretty quick response," the Holland executive said. The voyage was finalized in September.

Clipper service with Miami roots

Pan Am’s Clipper service was originally created as "ships of the air" but with high levels of comfort and elegance, said Craig Carter, chief executive officer for Pan American World Airways. That included multicourse meals served on fine china, and cocktail lounges. In 2024, Carter acquired the trademark, logo and intellectual property, including the name Pan American World Airways.

"Pan Am’s Clipper ships played a pivotal role in shaping modern air travel — and expanding tourism across the Caribbean," Holland said in a statement. With boatlike hulls, Clippers could land on water, transforming virtually any harbor into an airport and enabling access to destinations without established runways, the cruise line said.

Tracing history with a cruise

Of the 18 ports in the 2027 cruise, nine were original Pan Am destinations. They include Nassau, San Juan, Charlotte Amalie, St. John’s, Castries, Port of Spain, Colon and Progreso.

Nassau, Bahamas, was an early Pan Am destination in the Caribbean and what Holland considers "a cornerstone of regional aviation history." San Juan, Puerto Rico, was Pan Am’s link between South America and North America. Meanwhile, UNESCO World Heritage City Willemstad, Curacao, was a key refueling stop for the Allies during World War II.

Through themed meals, decor from the era, talks and multimedia presentations, Holland hopes to have "guests experience the magic of travel’s golden era."

The voyage won’t include stops in Cuba or Venezuela, key destinations for Pan Am in the early years.

The cost of the trip starts at $3,274 based on double occupancy, including taxes and fees.

Holland America’s collaboration with Pan Am is part of the cruise line’s commemoration of the United States’ 250th birthday.

Many details of what will take place during the cruise haven’t yet been finalized, Amy Carter, vice president of brands and licensing for Pan American World Airways, said in an interview with the Herald.

But she said some ideas include creating Pan Am-branded cocktail lounges and cocktails aboard the ship. Adding art from Pan Am’s heyday is also under consideration, as are showing films and having lectures.

"None of this is set in stone," she said.

Grigsby, the Holland executive, sees parallels between Holland’s history and that of Pan Am, such as its large network of destinations.

He wishes a former co-worker Andrew Sherry was around to see the cruise take place.

Sherry, who sat in an office next to the executive, died in 2015. Before joining Holland, he worked for Pan Am. He closed the door on the last Pan Am last flight out of Seattle, recalled Grigsby.

"I think about him," he said. "He made an impression on us."

Sherry often talked glowingly about Pan Am, Grigsby said.

"It’s something that runs in the blood."

Reservations

To get more information, including more details on the trip as they are unveiled as well as booking and pricing information, go to Holland’s website. To book tickets, talk to your travel agent, call 877-SAIL HAL (877-724-5425) or visit the cruise line online.

Itinerary for Pan Am 100th Anniversary Legendary Voyage

The stops after leaving PortMiami:

Nassau; Relax Away, Half Moon Cay, the carrier’s private island; Ocho Rios, Jamaica; Santo Domingo, Dominican Republic; San Juan; Charlotte Amalie, St. Thomas; St. John’s; Castries, St. Lucia; Port-of-Spain; Willemstad, Curaçao; Oranjestad, Aruba; Santa Marta, Colombia; Cartagena; Colon, Panama; Puerto Limon, Costa Rica; Belize City; Cozumel, Mexico; Progreso, Mexico; PortMiami