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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 (4.82)
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
Length
6 days
Rating (4.82)
Starts at
1,699
Program No. 20902RJ

Your well-being is our #1 priority

To make your experience as safe as possible, we require all participants to be fully vaccinated. See our Safety Roadmap

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We want your Road Scholar learning adventure to be something to look forward to—not worry about. Learn more

Prefer to enroll or inquire by phone? 800-454-5768
climate
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Select your type of room
Price will update based on selection
Prices displayed below are based on per person,doubleoccupancy.
DATES & starting prices
PRICES
Nov 13 - Nov 18, 2022
Starting at
1,799
Dec 4 - Dec 9, 2022
Starting at
1,699
Jan 8 - Jan 13, 2023
Starting at
2,399
Jan 22 - Jan 27, 2023
Starting at
2,399
Jan 29 - Feb 3, 2023
Starting at
2,449
Feb 5 - Feb 10, 2023
Starting at
2,449
Feb 12 - Feb 17, 2023
Starting at
2,449
Feb 26 - Mar 3, 2023
Starting at
2,449
Mar 5 - Mar 10, 2023
Starting at
2,499
Nov 12 - Nov 17, 2023
Starting at
2,049
Dec 3 - Dec 8, 2023
Starting at
1,999
DATES & starting prices
PRICES
Nov 13 - Nov 18, 2022
Starting at
2,549
Dec 4 - Dec 9, 2022
Starting at
2,349
Jan 8 - Jan 13, 2023
Starting at
3,479
Jan 22 - Jan 27, 2023
Starting at
3,479
Jan 29 - Feb 3, 2023
Starting at
3,529
Feb 5 - Feb 10, 2023
Starting at
3,529
Feb 12 - Feb 17, 2023
Starting at
3,529
Feb 26 - Mar 3, 2023
Starting at
3,529
Mar 5 - Mar 10, 2023
Starting at
3,639
Nov 12 - Nov 17, 2023
Starting at
2,879
Dec 3 - Dec 8, 2023
Starting at
2,739

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.
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.
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.
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.
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.
36 Reviews
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4.82 Average
(5)

5 stars for this relaxed visit to the historic sites of Key West led by the fabulous Craig. The hotel is perfectly located right on the water with lovely outdoor seating for a view of the harbor. While the itinerary was slower paced than we expected from the website description, we did enjoy all the sites we visited. Late starts of 9:00am for tour departures or lectures allowed for leisurely mornings. We walked slowly to each location with Craig, who used headphones to narrate each walk. All our tour guides were excellent, and our guest speakers in the hotel meeting room were excellent. A few highlights for us were the butterfly garden, Truman's Little White House, Hemingway's house (and the cats!), Tennessee Williams' home. Plan for humid and warm weather, and bring a bathing suit if you enjoy spending the free afternoon poolside. Lots of history and nature on this pleasant vacation.

(5)

This trip was wonderful. Not only do you stay at a lovely resort in a very central location, but you hear from outstanding instructors who really know their subject matter. We visited so many interesting places and ate amazing food. I would highly recommend this trip.

(5)

This was a great winter break. The program was varied and the city is lovely.

(5)

If you like to visit tropical destinations but want more to do than sit on a beach, this is the trip for you. There is so much rich cultural history in Key West that your days will filled with fascinating experiences steps from the fabulous resort that you'll stay in. The food is super fresh and healthy and there is so much variety. The shopping is great if you're interested. Very walkable town as it's flat and convenient to get to places by foot. Lots of things to do during free time. March 2022 visit

(5)

This was the second time we enrolled in this program. It was just as fun the second time around!

(5)

You may be thinking Key West is a dusty old island with boats, bars serving margaritas, and a place where Hemingway stayed for a while, but not much else. While Key West has those, there's a lot more to it than that. It's full of rich history, a place where artists, entrepreneurs, and presidents have made their home, and full of beautiful scenery. If your even mildly curious, take this short Key West trip and see for yourself. You won't regret it.

(5)

When my family and friends ask me how my trip to Key West was, my answer is, "Fabulous!". Road Scholar provided just the right combination of education, fellowship, and site visits.

This reviewer did not give a star rating.

Wonderful trip. Hotel and food were amazing. Our group leader, Craig, was so knowledgeable and organized. Learned so much about the culture and history of this beautiful city. Actually thinking about doing this trip again next year!

(2)

Excellent howeve coordinator quire average didn’t at provide eqsuggestions for free time. Rarelyused whispers. . No Covid vacvinecheck even though told by RS. There Seoul’s d Ed cautioned n. Q Thank special speakers all very informative and interesting.

(5)

Beautiful location. Diverse and varied activities. We went down early to explore some of the other Keys.

(5)

A great mid-winter getaway in a warm climate offering excellent accommodations in the heart of Key West, great meals at a variety of restaurants, interesting field trips and lectures, with time to explore on your own.

(5)

I highly recommend this program as it provides education, exercise and relaxation. The local speakers are all excellent; walking around Key West to the homes, museums and restaurants is easy and very pleasant as our leader uses the headsets to give us interesting tidbits of information on the way. Craig is an excellent leader giving us all of the information we need to enjoy ourselves and be happy that we came on this trip.

(5)

This was a fun and educational program with wonderful accomodations and lots of delicious foods. It is NOT a program for those with mobility issues.

(5)

The Road Scholar trip to Key West was fun and informative. I look forward to more adventures with Road Scholarsd!

(4)

An excellent typical Roadscholar excursion to Key West with well prepared speakers, venues, and appropriate excursions. Key West resident leader was quite helpful in allowing large group to enjoy the visit of 4 full days. Opal Resort is a comfortable older facility well maintained, with 2 elevators near the entrance so request rooms near the elevator to avoid long hallways. The variety and quality of the restaurants as well as a full breakfast was much appreciated. Multiple opportunities to enjoy Key Lime Pie. Recommend Bagatelle for dinner on your own. One might consider an extra day to take ferry $190 each to Dry Tortugas National Park. The Key West Airport will be replaced in 2024; it is appropriate for a provincial city in a banana republic. There are only 8 "gates" which means you may wait on arrival 30-90 minutes on the plane (we waited 30/others 90). Do not check luggage unless you wish to lose it or wait hours for grossly understaffed baggage facility. We had to wade through a mob of 100s awaiting luggage to get to the front door which was difficult for a spouse pushing a walker. Note peak times 11-2 pm to avoid long security lines (we left at 9 am) Use Lyft/Uber to hotel not overpriced taxis. Truman White House/Hemingway House were highlights of a full introduction to the charms of Key West One might consider a visit on your own to Zachary Taylor State Park entrance $2.50 for pedestrians. The full vibe of Key West especially the spirited bars and famous T shirt shops was fully available on Duval Street. Enjoy and relax!

(5)

First time back to Key West in forties years, a great time and learning experience with a great group of people, great escape from the winter weather up north!!

This reviewer did not give a star rating.

What a wonderful trip. The hosts were fantastic dealing with a larger than normal group. There was a complaint that the fish at the last lunch restaurant was way overcooked and the service was a bit iffy. Otherwise a great trip.

(5)

The Key West trip we enjoyed this December was a treat for the pre-holiday rush. Beautiful setting, lovey accommodations, friendly people, great trip leader. We left full of information and stories about Key West that we will love to share with others.

(5)

Road Scholar trips are not only interesting and informative, but are a great venue for friends and family members to spend time together in a new experience. Thumbs up!

(5)

The Signature City Key West program was just plain fun! The hotel was on the waterfront which gave views of sail boats at breakfast and over-the-water sunsets before dinner. Best of all, nearly all the activities and restaurants were within a comfortable walking distance on scenic and pedestrian-friendly streets. For those who like to stay out late, the night life was hopping with many bars, restaurants, musicians and local talent within easy walking distance. Most of the program time was spent visiting interesting historical Key West houses and museums interspersed with great food and key lime pie at locally owned restaurants. More than half the group was solo travelers and everyone mixed and mingled during events and while dining. There were plenty of other solos to venture forth with during free time and many new friendships were made. Craig, our incredibly organized and knowledgeable guide, made sure that everyone felt included and maximized both the fun and learning of the trip. This was an excellent learning adventure and a program to take if you want to learn, eat, explore and just have fun.

(4)

Overall a good program, especially if you like authors

(5)

This was a good trip to see the highlights of Key West. We stayed at The Reach hotel in Key West and it was very comfortable.

(5)

As a single women I really enjoy Road Scholar programs. I have always met interesting people and I have never felt left behind.

(5)

Great program, wonderful hotel and lots of good food. Only issue was the weather which Road Scholar cannot control. Key take away for Road Scholars always bring your base layer even when you go to Key West you never know when it might get cold!

(5)

What a great trip! Craig was an awesome group leader and Key West is an awesome town! We saw and learned a lot, and had a wonderful fun time doing it. And the food was incredible. Thanks you RS... It was definitely worth the price.

(5)

Great trip you will be happy

(5)

This was my first Road Scholar trip and my first time to Florida. The program was excellent. The group of 15 was a nice size and made it easy to get to know one another. The guide, tours, lectures, food were perfect. I enjoyed my trip and hope to take another RS excursion in the near future.

(5)

Excellent program, group was very enjoyable, leader outstanding.

(5)

what a great way to experience Key West! I feel like we covered everthing from a variety of foods, museums and culture. You could tell our host, Craig, really knows and loves his home of Key West

(5)

This program was varied and always interesting. I learned so much of the history on this small island.

(5)

This travel experience is great for those who want to do more than sit around on a beach all day !! Traveling with the group is much easier than doing all the preparations yourself. You find yourself immersed in the experience instead of overwhelmed by the planning.

(5)

Like our other two Road Scholar tours, this one to Key West was enjoyable, entertaining and educational. It's the best way to visit anywhere.

(4)

A delightful exposure to Key West with diverse visits to Hemingway's House, Mel Fisher Museum, Cultural Center, Tennessee Williams Museum and Coast Guard cutter, The sunset in Mallory Square is not to be believed- worth the trip! Craig was a great leader sharing his knowledge and enthusiasm with us.

(5)

Mike Fowler our leader on this trip was a gem. What a great leader a keen eye for what everyone was up to. Such care for all. The program was excellent and I have been to Key West 2 times before but not with the program details and excellence as this one.

(5)

Key West is a place unlike most other U.S. beach towns. This program hits all the historical highlights (and there are many), and gives additional perspectives on the town, what it's like to live there, and what makes it so special. Quick and active, it's very enjoyable and interesting.

(5)

Key West is often thought of as just a party town, truth is, there is much to see and much to learn in this really fun environment. The Truman White House and Butterfly House just two excellent examples!






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