If you’ve ever dreamed of stepping back into travel’s most glamorous era, Holland America Line just made it possible (and then some). The cruise line has teamed up with Pan Am to launch a 28-day journey that retraces the airline’s legendary flying Clipper routes across the Caribbean, Mexico, and Latin America. The Pan Am 100th Anniversary Legendary Voyage sets sail aboard the Zuiderdam on October 30, 2027, from Miami, Pan Am’s original home base, promising four exciting weeks of nostalgia and sunshine.
This isn’t your typical island-hop, though. The month-long itinerary hits 18 ports, including seven original Pan Am destinations like Nassau, San Juan, Willemstad, and Port of Spain. Guests can expect a mix of lively Caribbean capitals, hidden harbors, and cultural gems, from rum tastings and rainforests to art-filled streets and white-sand beaches.
A journey where history meets high seas

The voyage celebrates Pan Am’s centennial with themed events, vintage-inspired décor, and gourmet dining that channels the elegance of the 1930s flying era. Onboard talks and exhibits will share stories of Pan Am’s iconic Clippers – the seaplanes that first connected far-flung islands and helped shape global tourism.
“This collaboration is a tribute to the golden age of travel and humanity’s enduring drive to explore,” said Paul Grigsby, Holland America’s VP of itinerary planning.
From Half Moon Cay to Cartagena and back to Miami, the Legendary Voyage invites travelers to relive an age when travel wasn’t just about getting there, it was about the adventure itself.
Prices start around $4,000 USD.