Five Days in Key West: An Independent Adventure

Head to Key West for a mid-week adventure as you learn about the lives of famous residents of the past — from Hemingway to Truman — and come to see why this island city inspired them.
Rating (5)
Program No. 23602RJ
5 days
Starts at

At a Glance

Spend five lovely days in the sunny city of Key West at the Historic Curry Mansion Inn! Explore the island with local experts to hear stories of historical figures who have lived here — from pirates to playwrights to presidents. Hop on a bicycle and feel the warm, salty air on your face as you pedal to Hemingway’s House. Stop by to say hello to the spirit of Harry Truman at his Little White House, and learn about the life of Tennessee Williams at a museum dedicated to the famous playwright. Delve into the flora and fauna of Key West, and take in a live theatre performance during this mid-week seaside learning adventure. Plus, take advantage of lots of independent time to sail, kayak, snorkel or explore the architecture and maritime history of this four-square-mile island on foot, by bicycle or by trolley!
Independent City Discoveries
Independent City Discoveries
Learn with a Group Leader and enjoy educational programming while also getting independent time to explore on your own. Most Independent City Discoveries include lectures, self-guided excursions and passes for public transit and museums.

Best of all, you'll ...

  • Experience the sunset festival, a nightly Key West tradition since the 1960s — complete with jugglers, local musicians, artists and food vendors.
  • Take part in a literary bike tour as you cycle to Ernest Hemingway’s House.
  • Learn what Key West was like when President Harry Truman was a resident at his Little White House.

General Notes

Combine this program with our long-weekend Key West program to make it a full week and save $100! Give us a call to combine this program with "A Weekend in Key West: An Independent Adventure" (#23601).
Visit the Road Scholar Bookshop
You can find many of the books we recommend at the Road Scholar store on bookshop.org, a website that supports local bookstores.
Mile Marker Zero: The Moveable Feast of Key West
by William McKeen
For Hemingway and Fitzgerald, there was Paris in the twenties. For others, later, there was Greenwich Village, Big Sur, and Woodstock. But for an even later generation—one defined by the likes of Jimmy Buffett, Tom McGuane, and Hunter S. Thompson—there was another moveable feast: Key West, Florida. The small town on the two-by-four-mile island has long been an artistic haven, a wild refuge for people of all persuasions, and the inspirational home for a league of great American writers. Some of the artists went there to be literary he-men. Some went to re-create themselves. Others just went to disappear—and succeeded. No matter what inspired the trip, Key West in the seventies was the right place at the right time, where and when an astonishing collection of artists wove a web of creative inspiration.
Key West: History of an Island of Dreams
by Maureen Ogle
Parrotheads, Hemingway aficionados, and sun worshipers view Key West as a tropical paradise, and scores of writers have set tales of mystery and romance on the island. The city’s real story—told by Maureen Ogle in this lively and engaging illustrated account—is as fabulous as fiction. In the two centuries since the city’s pioneer founders battled Indians, pirates, and deadly disease, Key West has stood at the crossroads of American history. In 1861, Union troops seized control of strategically located Key West. In the early 1890s, Key West Cubans helped José Martí launch the Cuban revolution, and a few years later the battleship Maine steamed out of Key West harbor on its last, tragic voyage. At the turn of the century, a technological marvel—the overseas railroad—was built to connect mainland Florida to Key West, and in the 1920s and 1930s, painters, rumrunners, and writers (including Ernest Hemingway and Robert Frost) discovered Key West. During World War II, the federal government and the military war machine permanently altered the island’s landscape, and in the second half of the 20th century, bohemians, hippies, gays, and jet-setters began writing a new chapter in Key West’s social history.
Hemingway's Key West
by Stuart McIver
This vivid portrait reveals both Hemingway, the writer, and Hemingway, the hard-drinking, woman-chasing fighter and sportsman of legend. Hemingway's decade in Key West during the 1930s was his most productive. His only book set in the U.S., To Have and Have Not, takes place there. Meet his circle of friends (known as "the Mob"), his second wife, Pauline, and their two children. Hear from Hemingway contemporaries and scholars about the man and the town that he made famous.
To Have and Have Not
by Ernest Hemingway
This is the dramatic, brutal story of Harry Morgan and his efforts to support his family by running contraband between Key West and Cuba. Set in the 1930s, the book carries all the flavor of an era that was poor, tough and resourceful. Harshly realistic, yet with one of the most subtle and moving relationships in Hemingway's "oeuvre", it goes beyond high adventure. It was adapted for film and became a memorable classic, starring Humphrey Bogart and Lauren Bacall.
Last Train to Paradise: Henry Flagler and the Spectacular Rise and Fall of the Railroad that Crossed an Ocean
by Les Standiford
Last Train to Paradise is acclaimed novelist Les Standiford’s fast-paced and gripping true account of the extraordinary construction and spectacular demise of the Key West Railroad—one of the greatest engineering feats ever undertaken, destroyed in one fell swoop by the Labor Day hurricane of 1935.

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