✈️ A New Era Takes Flight: Honoring Pan Am®’s First Passenger Journey

Commemorating a milestone in American exploration, innovation, and partnership

On January 16, 1928, a small crowd gathered in Key West, Florida, to witness something quietly revolutionary: a Fokker F7 aircraft preparing to depart for Havana, Cuba. This wasn’t Pan American Airways’ first time flying the route; the airline had been carrying mail across the Florida Straits since October 1927. But this 90-mile flight was different, because today it would carry fare-paying passengers for the very first time — and help launch the United States into the age of international air travel.

By mid-January 1928, Pan Am® had upgraded its Key West facilities to support passenger service. Two sturdy Fokker F7 aircraft (General New and General Machado) were readied for the historic occasion.

• General New carried mostly mail along with one nonpaying passenger: Pan Am® founder Juan Trippe, who insisted on experiencing the moment firsthand
• General Machado carried the first official fare-paying passengers, who had shelled out $50 for the one-hour journey to Havana — a considerable sum at the time, but a small price to pay for the promise of a new frontier
• The flight was smooth, swift, and symbolic. As General Machado’s wheels touched down in Havana, Pan Am® officially began transitioning from a humble mail carrier to the world’s first truly global airline.

Pan Am®’s first passenger flight was more than a milestone — it was a declaration of intent.

• It marked the beginning of Pan Am®’s evolution into the United States’ most influential international airline, often referred to as America’s “Chosen Instrument” of global aviation
• It validated Juan Trippe’s bold vision for accessible international air travel
• It set the stage for rapid expansion across Latin America
• Within the same year, Pan Am® accelerated its growth and reach by adding larger aircraft including Fokker trimotors and Sikorsky amphibians

This single flight became the spark that ignited decades of innovation, adventure, and global connection.

Holland America and Pan Am® share a deep heritage rooted in discovery. Both brands have carried generations of travelers across borders, oceans, and cultures — connecting them to the world and to each other.

Today, Holland America is proud to honor that legacy through its exclusive partnership with Pan Am®, honoring the airline’s pioneering spirit as it approaches its 100th anniversary. Together, these two travel icons are celebrating innovation, heritage, and the art of leisurely travel with a commemorative 100th Anniversary voyage, carefully crafted to follow the historic routes of Pan Am®’s famous Clipper planes across the Caribbean and Mexico.

Pan Am® is also a proud partner of Holland America’s United States 250th Anniversary celebration in 2026, helping mark the nation’s upcoming semiquincentennial by honoring stories of American ingenuity — stories like this one.

As we look back at Pan Am®’s first passenger flight, we’re reminded that when it comes to imagination, determination, and innovation, the sky’s the limit.

Explore Holland America’s 28-Day Pan Am® 100th Anniversary Legendary Voyage and rediscover the Golden Age of Travel.