Next year marks the 100th anniversary of Pan Am, the pioneering airline that reshaped modern travel. To celebrate this milestone, Holland America Line will revive Pan Am’s legendary Clipper routes at sea. Beginning Oct. 30, 2027, the cruise line’s 28-day Pan Am 100th Anniversary Legendary Voyage will follow the original “flying boat” paths through Mexico, the Caribbean and Latin America.
© Holland America Line
Sailing aboard Zuiderdam, the voyage departs from Miami—Pan Am’s historic home base—and visits 18 ports, nearly half of which align with stops on Pan Am’s original Great Circle Route. Rather than a standard cruise, the itinerary emphasizes immersive exploration of lesser-known and harder-to-reach destinations, giving guests a chance to experience diverse histories, cultures and landscapes.
Highlights include San Juan, Puerto Rico, a cultural crossroads that once connected Pan Am’s Caribbean network with North and South America; Willemstad, Curaçao, an island city that served as a strategic refueling point during World War II; and Trinidad and Tobago, known for its vibrant cultural traditions.
Pan Am flight service training in the 1950s © Holland America Line
The voyage also features period-inspired décor, themed meals and historical programming that evoke the golden age of travel. These curated experiences aim to recreate the spirit of the Clipper era while offering modern comfort and service.
Pan Am’s Clipper flying boats were technological innovations that helped open the Caribbean to widespread tourism. With hulls designed to land on water, these aircraft turned coastal harbors into makeshift airports and allowed passengers to disembark for overnight stays before reboarding to continue their journeys. That blend of mobility and local immersion played a significant role in connecting far-flung destinations and shaping mid-20th-century travel.
By retracing Clipper routes on a contemporary cruise ship, the anniversary voyage seeks to honor Pan Am’s legacy—bringing together maritime travel, historical storytelling and regional discovery for guests who want a deeper, more atmospheric way to travel the Caribbean and beyond.