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20902
Florida

Signature City Key West

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.
Rating (4.88)
Program No. 20902RJ
Length
6 days
Starts at
1,699
Florida

Signature City Key West

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.
Length
6 days
Starts at
1,699
Program No. 20902 RJ
Prefer to enroll or inquire by phone? 800-454-5768
climate
Plan ahead.
What kind of weather can you expect? Take a look!
itinerary
Please Note:
The itinerary for this program is different on certain dates.
Select your type of room
Price will update based on selection
Prices displayed below are based on per person,doubleoccupancy.
DATES & starting prices
PRICES
Dec 12 - Dec 17, 2021
Starting at
1,699
Itinerary Note

This program will take place at the Margaritaville Resort in Key West's Old Town.

Jan 9 - Jan 14, 2022
Starting at
2,049
Feb 13 - Feb 18, 2022
Starting at
2,349
Mar 6 - Mar 11, 2022
Starting at
2,349
Nov 13 - Nov 18, 2022
Starting at
1,799
Dec 4 - Dec 9, 2022
Starting at
1,699
DATES & starting prices
PRICES
Dec 12 - Dec 17, 2021
Starting at
2,299
Itinerary Note

This program will take place at the Margaritaville Resort in Key West's Old Town.

Jan 9 - Jan 14, 2022
Starting at
2,999
Feb 13 - Feb 18, 2022
Starting at
3,349
Mar 6 - Mar 11, 2022
Starting at
3,349
Nov 13 - Nov 18, 2022
Starting at
2,549
Dec 4 - Dec 9, 2022
Starting at
2,349

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 United States’ southernmost city so unique and 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.

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 be interested in a more leisurely version of this program, "Key West at a Slower Pace: Living on Island Time" (#21797).
Featured Expert
All Experts
Profile Image
Bob Wolz
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.

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

Profile Image of Bob Wolz
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.
Profile Image of Alex Okinczyc
Alex Okinczyc View biography
Alex Okinczyc, a longtime resident of Key West, is an experienced deep sea diver who shares his stories through humor, connecting with his audience and music! Okinczyc brings his treasures from the sea to tell us about his passion for deep sea diving and for Key West.
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.
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.
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.
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.
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."
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.





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