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Florida

Signature City Key West

Program No. 20902RJ

Dive deep into the legends, history, artistic legacy and natural wonders of one of Florida’s most vibrant cities as you unravel the mysteries of Old Town, Key West.

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6 days

5 nights

12 meals

5B 3L 4D

Check-in, Registration, Orientation, Welcome Dinner

Key West Old Town

Harry Truman, Little White House, Custom House

Key West Old Town

Audubon Lecture & House, USCGC Ingham

Key West Old Town

Mel Fisher Museum, Free Time

Key West Old Town

Hemingway, Tennessee Williams, Eco Discovery Center

Key West Old Town

Program Concludes

Key West Old Town

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At a Glance

With its distinctive architecture, courtyard gardens and hidden pathways, Key West’s Old Town is a delight to explore on foot. Experience what makes the southernmost city in the contiguous United States so unique, and explore what lies behind the quaint facade. With local experts, hear tales of shipwrecks, explore the Hemingway home and get a look at Papa’s favorite bar. Consider President Truman’s love affair with Key West at the “Little White House” and share the spirit of the island with artists, divers, gardeners, historians, musicians, oceanographers and other natives.

Activity Level

Keep the Pace

Walking two miles daily on paved sidewalks; some stairs and standing at museums and historic sites.

Small Group

Love to learn and explore in a small-group setting? These adventures offer small, personal experiences with groups of 13 to 24 participants.

Best of all, you’ll…

Meet numerous Key West residents and hear from them about their home and the cultural scene.
Visit the Mel Fisher Maritime Museum to examine artifacts retrieved from a sunken 17th-century ship.
Learn about the variety of bird species and exotic flora at the Audubon House and Tropical Gardens.

General Notes

You may enjoy a slower-paced program, "Key West at a Slower Pace: Living on Island Time" (#21797)

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.

Craig Wanous View biography

Craig Wanous was born and raised in Alabama, but has lived in the Florida Keys and Key West since 1990. He and his wife came to the Keys after an 18-month cruise on their sailboat. Craig became involved with Road Scholar after hosting the groups at the visitor center where he worked. He has been leading Road Scholar tours in Key West since 2014, and always enjoys the curiosity and appetite for learning shown by participants.

Joanne Martin View biography

Kristina Agard View biography

Kristina Agard grew up on Long Island Sound in southeastern Connecticut, attending/working summer camps at Project Oceanology. After graduating with a B.S. in marine biology from the University of New Hampshire, she came to the Keys to work at Seacamp on Big Pine Key, and has remained in the area ever since. Kristina has a two-decade career in marine science education and outreach that includes teaching in Long Island Sound, the Gulf of Maine, Puget Sound, and the Florida Keys National Marine Sanctuary.

Suggested Reading List (6 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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Signature City Key West

Program Number: 20902

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.

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.

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.

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.

Tom: The Unknown Tennessee Williams

by Lyle Leverich

The riveting, revelatory, and sole authorized account of the critical first decades of Tennessee Williams's life. Tennessee Williams, author of such indelible masterpieces as The Glass Menagerie and A Streetcar Named Desire, is considered by many to be the greatest literary artist of the American theater. Tom is Lyle Leverich's definitive account based on his exclusive access to letters, diaries, unpublished manuscripts, and family documents of Williams's early life and of the events that shaped this most autobiographical of dramatists. It tells the story of the marital traumas of his bullying father and overly protective mother, the mental disorders that institutionalized his beloved sister Rose, his stalled academic career, and his confused sexuality and early successes as a writer; and it leaves Thomas Lanier Williams on the brink of fame with The Glass Menagerie and his transformation into the celebrated persona of "Tennessee."

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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Signature City Key West

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At a Glance

Best of all, you’ll…

General Notes

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