This Roundtrip Cruise From Miami Will Visit 18 Ports in the Caribbean

Holland America Line has announced a new Caribbean itinerary that’s set to make history. The 28-day Pan Am 100th Anniversary Legendary Voyage, sailing roundtrip from Miami on October 30, 2027, will visit 18 ports across nine Caribbean and Latin American destinations.

The cruise, sailing aboard Zuiderdam, is inspired by Pan Am’s original Clipper routes and celebrates a century of aviation milestones along with a shared spirit of exploration. The voyage is part of Holland America’s wider celebration of America’s 250th anniversary, which includes collaborations with other iconic American brands that shaped modern travel.

18 Ports, 9 Countries, 28 Days

Holland America’s latest itinerary is one of the most extensive Caribbean sailings the line has ever offered. Departing from Miami on October 30, 2027, the Zuiderdam will visit a remarkable mix of destinations across the Caribbean, Mexico, and Latin America before returning to Florida at the end of the voyage.

The sailing commemorates the 100th anniversary of Pan American Airways, retracing the airline’s historic Clipper routes that once connected travelers to far-flung island destinations. It also forms part of Holland America’s recognition of America’s 250th anniversary, featuring heritage partnerships that celebrate innovation and exploration.

The commemorative voyage will give guests a true taste of the Caribbean and beyond, calling at 18 ports across nine countries. It features a blend of classic destinations, private islands, and hidden gems rarely combined in one itinerary.

Here’s the full itinerary:

Day 1 – Oct 30, 2027: Miami, Florida, US
Day 2 – Oct 31, 2027: Nassau, Bahamas
Day 3 – Nov 1, 2027: Half Moon Cay, Bahamas
Day 4 – Nov 2, 2027: Day at Sea
Day 5 – Nov 3, 2027: Ocho Rios, Jamaica
Day 6 – Nov 4, 2027: Day at Sea
Day 7 – Nov 5, 2027: Santo Domingo, Dominican Republic
Day 8 – Nov 6, 2027: San Juan, Puerto Rico
Day 9 – Nov 7, 2027: St. Thomas, U.S. Virgin Islands
Day 10 – Nov 8, 2027: St. John’s, Antigua and Barbuda
Day 11 – Nov 9, 2027: Castries, Saint Lucia
Day 12 – Nov 10, 2027: Port of Spain, Trinidad and Tobago
Day 13 – Nov 11, 2027: Day at Sea
Day 14 – Nov 12, 2027: Willemstad, Curaçao
Day 15 – Nov 13, 2027: Oranjestad, Aruba
Day 16 – Nov 14, 2027: Day at Sea
Day 17 – Nov 15, 2027: Santa Marta, Colombia
Day 18 – Nov 16, 2027: Cartagena, Colombia
Day 19 – Nov 17, 2027: Day at Sea
Day 20 – Nov 18, 2027: Colón, Panama
Day 21 – Nov 19, 2027: Puerto Limón (San José), Costa Rica
Days 22–23 – Nov 20–21, 2027: Days at Sea
Day 24 – Nov 22, 2027: Belize City, Belize
Day 25 – Nov 23, 2027: Cozumel, Mexico
Day 26 – Nov 24, 2027: Day at Sea
Day 27 – Nov 25, 2027: Progreso (Mérida), Yucatán, Mexico
Day 28 – Nov 26, 2027: Day at Sea
Day 29 – Nov 27, 2027: Miami, Florida, US

Holland America’s 28-day sailing retraces many of those same routes, offering guests the chance to experience the region much like early 20th-century travelers once did, now with the comfort and elegance of a modern cruise ship. Each port of call has been carefully selected to capture the pioneering spirit that defined Pan Am’s early days.

Life Onboard Zuiderdam

Guests sailing on the Pan Am 100th Anniversary Legendary Voyage will experience the comfort and classic style that Holland America Line is known for. Zuiderdam combines timeless design with modern amenities, offering a relaxed yet refined atmosphere throughout the 28-day journey.

Accommodation options range from spacious suites to well-appointed staterooms, all featuring Holland America’s signature Mariner’s Dream beds, plush Euro-Top mattresses, and premium Elemis bath products. Guests can also enjoy complimentary 24-hour room service, daily housekeeping, and a range of onboard entertainment.

Evenings on board bring live music and performances across multiple venues. The World Stage theater showcases visually immersive productions, while the Rolling Stone Lounge and Billboard Onboard feature music ranging from pop and rock to chart-topping classics. Dining options include Holland America favorites such as Pinnacle Grill, Canaletto, and the Lido Market, offering a variety of cuisines as guests sail through the Caribbean.

Booking and Official Details

Bookings are now open for the 28-day Pan Am 100th Anniversary Legendary Voyage aboard Zuiderdam. The cruise departs from Miami, Florida, on October 30, 2027, and returns to Miami at the end of the itinerary. Travelers can view full details, pricing, and stateroom availability on Holland America Line’s official website.

Guests booking directly through Holland America can also take advantage of the line’s Flight Ease program, offering flexible airfare options with late arrival protection and 24-hour support. A selection of shore excursions will be available to pre-book, including island tours, snorkeling adventures, and cultural experiences that highlight each destination’s local heritage.

With a limited number of sailings and an itinerary that celebrates both Pan Am’s legacy and America’s 250th anniversary, this cruise is expected to attract strong interest from cruisers seeking a one-of-a-kind Caribbean experience.

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