Next year is the 100^th anniversary of Pan Am, the airline that changed modern travel as we know it. To honor the historic airline, Holland America Line brings Pan Am’s iconic Clipper routes to sea. Launching Oct. 30, 2027, the cruise line’s 28-day Pan Am 100^th Anniversary Legendary Voyage will retrace the original “flying boat” paths across Mexico, the Caribbean and Latin America.

© Holland America Line

Taking place onboard Zuiderdam, the voyage will depart from Miami, Pan Am’s historic homebase, and stop at 18 destinations, nearly half of which were featured on Pan Am’s original Great Circle Route. The itinerary is far from the typical cruise voyage, offering immersive exploration of harder-to-reach destinations for guests to dive into diverse histories, cultures and landscapes.

Stops include San Juan, Puerto Rico, a cultural hub that first linked Pan Am’s Caribbean network to both North and South America; Willemstad, Curaçao, a city that served as a strategic refueling stop during Allied operations in World War II; and Trinidad and Tobago.

Pan Am flight service training in the 1950s © Holland America Line

The trip also includes themed meals, period-inspired décor and historic programming.

Pan Am’s Clipper ships were innovative aircraft that contributed to the expansion of tourism across the Caribbean. These vessels had boat-like hulls (hence its nickname of “flying boats”) and could land on water, transforming any harbor into an airport. The aircraft let passengers disembark, stay overnight at local hotels and reboard to continue to the next destination.