Roundtrip Cruise From Miami to 18 Beautiful Caribbean Ports
Holland America Line is celebrating both the spirit of adventure and America’s rich history with the launch of a new roundtrip cruise from Miami. Set to depart on October 30, 2027, this 28-day journey aboard the Zuiderdam will visit 18 ports across the Caribbean, retracing the original flying Clipper routes once charted by Pan American World Airways (Pan Am).
The trip, dubbed the Pan Am 100th Anniversary Legendary Voyage, is inspired by the iconic airline’s “flying boat” routes, offering an exciting historical twist to a tropical cruise.
This immersive voyage is more than just a scenic tour of the Caribbean. It’s a unique blend of nostalgia and exploration, bringing travelers to both well-known and less-traveled destinations.
The cruise will make stops at several original Pan Am destinations, including Nassau, Bahamas; Ocho Rios, Jamaica; Santo Domingo, Dominican Republic; and San Juan, Puerto Rico. Altogether, the cruise will visit nine of these historic ports and 18 total across the Caribbean, Mexico, and Latin America.

Among the key stops on this exciting itinerary are:
- Nassau, Bahamas
- Half Moon Cay, Bahamas
- Ocho Rios, Jamaica
- Santo Domingo, Dominican Republic
- San Juan, Puerto Rico
- St. Thomas, US Virgin Islands
- St. John, US Virgin Islands
- Castries, St. Lucia
- Port-of-Spain, Trinidad
- Willemstad, Curaçao
- Oranjestad, Aruba
- Santa Maria, Colombia
- Cartagena, Colombia
- Colon, Panama
- Puerto Limon, Costa Rica
- Belize City, Belize
- Cozumel, Mexico
- Progreso, Mexico
In addition to its impressive roster of ports, the cruise marks a significant milestone for Holland America Line as it collaborates with Pan Am to honor America’s 250th anniversary. Both companies share a legacy of pioneering modern travel—Pan Am in the skies and Holland America Line on the seas.
Kacy Cole, Chief Marketing Officer for Holland America Line, explained, “Pan Am is an iconic American brand, and we are proud to partner with them to celebrate America’s rich heritage. By combining the legacy of Pan Am with Holland America Line’s extensive seafaring history, we are offering guests a chance to experience the same spirit of adventure and discovery that helped shape the nation.”
Paul Grigsby, Vice President of Itinerary Planning and Deployment for Holland America Line, echoed this sentiment, noting that both Pan Am and Holland America Line helped define the modern travel experience. He added, “With roots stretching over a century, both brands share a deep connection to exploring the world and creating lasting memories for travelers.“
This historic voyage offers more than just a getaway; it’s a chance for travelers to relive a key part of aviation and maritime history while enjoying the luxury and service Holland America is known for. With 18 ports to explore, this journey promises an unforgettable adventure for those seeking to combine relaxation with cultural immersion.
For more info and pricing on this itinerary, click here to go directly to Holland America’s website.