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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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
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.

What You'll Learn

  • 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

Featured Expert
All trip 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 Johnny Layton
Johnny Layton View biography
Johnny Layton has been leading programs for Road Scholar since 2017. From the Florida Keys to Alaska, Johnny has led programs in 11 states and four countries. When he is not ensuring Road Scholar participants are having an amazing experience, you can find him in the sky crisscrossing the USA as a flight attendant or as a driver/guide on the Historic Trolley Tour at home in Asheville, North Carolina.
Profile Image of Craig Wanous
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.
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.
While we make every effort to ensure the accuracy of our published materials, programs are typically advertised more than a year prior to their start date. As a result, some program activities, schedules, accommodations, personnel, and other logistics occasionally change due to local conditions or circumstances. Should a major change occur, we will make every effort to alert you. For less significant changes, we will update you during orientation. Thank you for your understanding.
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6 days
5 nights
12 meals
5 B 3 L 4 D
DAY
1
Check-in, Registration, Orientation, Welcome Dinner
Key West Old Town
D
Opal Key Resort & Marina

Activity note: Hotel check-in available from 3:00 p.m. Remember to bring your nametag (sent previously).

Afternoon: Program Registration: 3:00 p.m. After you check in and have your room assignment, join us at the Road Scholar table in the lobby to register with the program staff, get any updated information, and confirm the time and location of the Orientation session. If you arrive late, please locate your Group Leader and let them know you have arrived. Orientation: 5:30 p.m. The Group Leader will greet everyone and lead introductions. We will review the up-to-date program schedule, discuss roles and responsibilities, logistics, safety guidelines, emergency procedures, and answer questions. We will learn from a series of local experts who will give lectures and lead field trips. Most of our travel to and from program sites will be on foot, but one day will involve travel by trolley. Periods in the schedule designated as “Free time” and “At leisure” offer opportunities to do what you like and make your experience even more meaningful and memorable according to your personal preferences. The Group Leader will be happy to offer suggestions. Program activities, schedules, personnel, and indicated distances or times may change due to local circumstances/current conditions. In the event of changes, we will alert you as quickly as possible. Thank you for your understanding.

Dinner: At the hotel.

Evening: At leisure. Continue getting to know your fellow Road Scholars, settle in, and get a good night’s rest for the day ahead.

DAY
2
Harry Truman, Little White House, Custom House
Key West Old Town
B,L,D
Opal Key Resort & Marina

Activity note: Walking up to 2 miles today on paved sidewalks along busy streets; walking and standing for up to an hour at a time at sites.

Breakfast: At the hotel.

Morning: Our Truman expert will tell us all about the President’s days in Key West and what came to be known as The Little White House. Florida’s only Presidential site, the Harry S. Truman Little White House was constructed in 1890 as housing for naval officers. Its most important usage was as President Truman’s “Winter White House” from 1946 to 1952. We will then head over on foot to the Little White House. President Harry S. Truman’s first 19 months were grueling and left him physically exhausted. His doctor ordered a warm vacation and Key West was chosen as the location. President and Mrs. Truman arrived in November 1946 for a week of relaxation. He fell in love with the climate and small-town charm and returned to what became known as the Little White House for 11 presidential working vacations and five post-presidential trips after leaving office. Truman claimed Key West was his second favorite place on earth, surpassed only by his hometown of Independence, Missouri.

Lunch: At a local restaurant.

Afternoon: After lunch, we will go on a field trip to the Custom House Museum. This living link to Key West’s historic past was built in 1891 to house the island’s customs office, postal service, and district courts. “Old 91” is now the headquarters of the Key West Art and Historical Society that maintains a collection of artifacts and art significant to the Florida Keys. A local expert will lead us through this amazing space.

Dinner: At a local restaurant.

Evening: After dinner, we will get to try out our dance moves in a salsa class taught by a local expert.

DAY
3
Audubon Lecture & House, Walking Field Trip, USCGC Ingham
Key West Old Town
B,L,D
Opal Key Resort & Marina

Activity note: Walking up to 2 miles to travel to our destinations, and up to 1 mile during the walking field trip – approximately 1 hour – with breaks in between. Standing up to 1 hour and climbing a flight of stairs at the Audubon House. Remember to wear comfortable shoes, use sunscreen, and wear a hat.

Breakfast: At the hotel.

Morning: At the hotel, we will learn from a local expert about John James Audubon, America’s greatest wildlife artist and early naturalist. Audubon began exploring Florida in 1831 and visited the Keys and Dry Tortugas the next year. He left having seen 22 different bird species, and created drawings of each for his “Birds of America” folio. After the lecture, we will go on an expert-led exploration of the Audubon House and Gardens, the place Audubon lived and worked while in Key West which was then the home of one of the town’s founders. In the center of the lot was a garden of native and imported tropical plants Audubon used in his images of local birds. We will learn about Audubon’s life and work there as well as the history of the house itself, which was the first restoration project in Key West in 1958 and is still considered the gem of the island’s restoration movement. The home also displays 28 first-edition Audubon works. After our visit, we will set out on a guided excursion walking Key West's streets, taking in its intricate architecture and vast array of colors. Hear from a local expert about Key West's rich history of the US Navy presence as well as the heyday of the wrecking, sponging and cigar industries. This walk covers about a mile and requires about one hour to complete.

Lunch: At a local restaurant.

Afternoon: After lunch, we will visit the USCGC Ingham, a National Historic Landmark preserved off shore in Key West’s Truman Waterfront Park. With an expert, we will learn about the modern maritime history of the U.S. Coast Guard and learn about the Ingham’s 50 years of service in war and peacetime.

Dinner: At a restaurant near Mallory Square.

Evening: Prior to dinner, you have the option to enjoy the Sunset Celebration at Mallory Square Dock. In Key West, watching the sun go down is a daily ritual accompanied by a festival with arts and crafts exhibitors, street performers, vendors, and a crowd of thousands of locals and visitors alike. People begin gathering about two hours before sunset for this multicultural “happening” that embodies the spirit of Key West. Following dinner, the remainder of the evening is at leisure.

DAY
4
Mel Fisher Museum, Free Time
Key West Old Town
B
Opal Key Resort & Marina

Activity note: Mel Fisher Museum is next to the hotel. An elevator is available at the Mel Fisher Museum, though you may need to climb a flight of stairs to reach some parts of the facility. Walking and other free time activities according to personal choice.

Breakfast: At the hotel.

Morning: This morning we will visit the Mel Fisher Maritime Museum where we will learn about marine archaeology and see treasures, including gold and silver bars, retrieved from beneath the sea. Dedicated to educating the public on maritime and colonial activity in the New World and preserving maritime culture resources, the museum celebrates 500 years of history. As a special highlight, we will go behind the scenes and explore the conservation lab.

Lunch: On your own to sample the daytime local fare. Your Group Leader will be happy to offer recommendations.

Afternoon: Free time. This period of time has been set aside for your personal independent exploration to see and do what interests you most. Please refer to the list of Free Time Opportunities. The Group Leader will be happy to offer suggestions. Please note that the period scheduled for free time is subject to change depending on local circumstances and opportunities for independent exploration.

Dinner: On your own.

Evening: At leisure. Enjoy a stroll to view the passing parade, or, if you’re feeling adventurous, wet your whistle in one of Hemingway's favorite hangouts. Hint: Two local bars lay claim to being his “real” favorite. Again, you have the suggestion to check-out the Sunset Celebration at Mallory Square Dock. In Key West, watching the sun go down is a daily ritual accompanied by a festival with arts and crafts exhibitors, street performers, vendors, and a crowd of thousands of locals and visitors alike. People begin gathering about two hours before sunset for this multicultural “happening” that embodies the spirit of Key West.

DAY
5
Hemingway, Tennessee Williams, Butterfly Gardens
Key West Old Town
B,L,D
Opal Key Resort & Marina

Activity note: Walking up to 1.5 miles to travel to our destinations and standing at sites for up to an hour at a time; climbing a flight of stairs at the Hemingway House and at lunch. Climbing four steps to ride a trolley to Hemingway House and from the Butterfly Gardens.

Breakfast: At the hotel.

Morning: We will go on a literary journey of Key West starting with the Hemingway House, which we’ll reach by trolley. There, a local expert will lead us through the former residence of one of America’s most iconic writers, whose personal life was as colorful as any of his characters. Ernest Hemingway first visited Key West in 1928, arriving from Havana. We will learn about the lives and times of Hemingway and his wife, Pauline, in Key West, and about the house itself. Personal touches are still visible throughout the house, from European antiques to trophies and skins which are the legacy of Hemingway’s African safaris. It was at the house that Hemingway produced some of his best known works including “To Have And Have Not,” which is set in Key West. Descendants of his six-toed cat still flourish there. Afterwards, we will learn about Key West literary figure Tennessee Williams during an expert-led visit to an exhibit dedicated to the playwright.

Lunch: At a local restaurant.

Afternoon: After lunch, we will visit the Key West Butterfly and Nature Conservatory where we will see and learn from an expert staff member about exotic butterflies, plants, and birds in this beautiful, glass-enclosed habitat. From there, we will board the trolley and make our way to dinner.

Dinner: At a local restaurant. Share favorite experiences and enjoy camaraderie with new Road Scholar friends during our farewell dinner.

Evening: At leisure. Prepare for check-out and departure in the morning.

DAY
6
Program Concludes
Key West Old Town
B

Activity note: Hotel check-out by 11:00 a.m.

Breakfast: At the hotel. This concludes our program.

Morning: If you are returning home, safe travels. If you are staying on independently, have a wonderful time. If you are transferring to another Road Scholar program, detailed instructions are included in your Information Packet for that program. We hope you enjoy Road Scholar learning adventures and look forward to having you on rewarding programs in the future. Don’t forget to join our Facebook page and follow us on Instagram. Best wishes for all your journeys!






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