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Florida

Key West at a Slower Pace: Living on Island Time

Program No. 21797RJ

Find out what makes Key West such a unique city as you stroll its vibrant streets, discovering its heritage, culture, world-class museums and the true spirit of island life.

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6 days

5 nights

12 meals

5B 3L 4D

Check-in, Orientation, Welcome Dinner

Key West Old Town

Boat Cruise, Key West Trolley

Key West Old Town

Hemingway House, Tennessee Williams, San Carlos Institute

Key West Old Town

Audubon Lecture & House, Custom House, Free Time

Key West Old Town

Little White House, Mel Fisher

Key West Old Town

Program Concludes

Key West Old Town

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At a Glance

Don’t let the quaint, small-town façade fool you — there’s a lot more to Key West than meets the eye. Discover all its hidden treasures at an easy pace befitting this laid-back island city. Navigate by trolley to experience its rich history and the unique pace of life on “island time.” Appreciate the blend of Victorian, Bahaman and New England architecture in its iconic “conch houses.” Hear tales of ships and shipwrecks and walk in the footsteps of larger-than-life figures like Hemingway and President Truman. Share the spirit of the island with artists, divers, gardeners, historians, musicians, oceanographers and other experts who reveal the city through the eyes of Key West natives.

Activity Level

On Your Feet

Walking up to one mile on even terrain.

Best of all, you’ll…

Go inside the structure that gave birth to Key West’s historical restoration movement, the Audubon House, where you can see 28 first-edition works by James Audubon.
Navigate the Customs House Museum, a living link to Key West’s historic past and home to art and artifacts that tell the story of this island town.
Learn about life in Key West when Ernest Hemingway and President Harry Truman were residents during explorations of the Hemingway House and Truman's Little White House.

General Notes

You may be interested in a more active version of this program, "Signature City Key West" (#20902).

Featured Expert

All trip experts

Joanne Martin

Joanne Martin grew up in the Greater Boston area, and has lived in Key West for nearly two decades. Over the years, she has worked in sales, marketing, and the travel industry. Her love of history led her to her current job as gallery manager at the Audubon House and Tropical Gardens where she has been since 2014, starting out leading visitors there.

Please note: This expert may not be available for every date of this program.

Bob Wolz View biography

Bob graduated from Youngstown State University, majoring in history with a minor in business. In 1999, he became the executive director of the Harry S. Truman Little White House State Historic Site. Bob created a not-for-profit corporation that aims to expand educational outreach of the Little White House and complete its restoration. He is an accomplished writer, having co-authored or edited several books including 'Presidents in Paradise.' His work has also appeared in the Florida Artland History Magazine and the American Political Science Review.

Lynn Wanous View biography

Lynn Wanous and her family sailed into the Florida Keys on their sailboat in 1990s. Lynn has fully embraced the island culture and is now a "fresh water conch," a term for long-time non-native residents of Key West. She worked at Edward Jones Financial Services and won the prestigious Spirit of Caring Award, given annually to only one employee in the entire company. Lynn has been leading Road Scholar Key West groups since 2018.

Joanne Martin View biography

Suggested Reading List (5 books)

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.

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Key West at a Slower Pace: Living on Island Time

Program Number: 21797

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.

Key West: History of an Island of Dreams

by Maureen Ogle

Parrotheads, Hemingway aficionados, and sun worshippers 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.

Notebooks

by Tennessee Williams & Margaret Thornton

Tennessee Williams’s Notebooks, here published for the first time, presents by turns a passionate, whimsical, movingly lyrical, self-reflective, and completely uninhibited record of the life of this monumental American genius from 1936 to 1981, the year of his death. In these pages Williams (1911-1981) wrote out his most private thoughts as well as sketches of plays, poems, and accounts of his social, professional, and sexual encounters. The notebooks are the repository of Williams’s fears, obsessions, passions, and contradictions, and they form possibly the most spontaneous self-portrait by any writer in American history.

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.

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.

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Key West at a Slower Pace: Living on Island Time

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At a Glance

Best of all, you’ll…

General Notes

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