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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Itinerary
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.
Read More.
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.
Duration
6 days
5 nights
What's Included
12 meals (
5B, 3L, 4D
)
2 expert-led lectures
9 expert-led field trips
1 hands-on experience
An experienced Group Leader
5 nights of accommodations
Taxes and customary gratuity
Road Scholar Assurance Plan
Day
1
Check-in, Registration, Orientation, Welcome Dinner
Location:
Key West Old Town
Meals:
D
Stay:
The Marker
Activity Note
Hotel check-in available from 4:00 p.m. Remember to bring your nametag (sent previously).
Afternoon:
Hotel check in is at 4:00 p.m. Program Registration: 3:00-5:00 p.m. Join us at the Road Scholar table in the lobby to meet with 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
Location:
Key West Old Town
Meals:
B,L,D
Stay:
The Marker
Activity Note
Walking up to 2.5 miles spread throughout the day, on paved sidewalks along busy streets; walking and standing for up to an hour at a time. Please note that the elevator at Custom House is currently out of order, so any participants who cannot manage stairs will not have access to the second floor. Remember to wear comfortable shoes, use sunscreen, and wear a hat.
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, USCGC Ingham
Location:
Key West Old Town
Meals:
B,L,D
Stay:
The Marker
Activity Note
Walking up to either 2 or 3.2 miles, spread throughout the day, to our destinations. In the afternoon, participants have the option to walk 1.2 miles with the group leader back to the hotel. Or if they prefer not to walk, they may take the free public shuttle, "The Duval Loop", back to the hotel. Additionally, 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.
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. The afternoon's scheduled activities will end at the Ingham. From here, you have several hours before the group re-gathers for dinner. You may chose to continue to explore the city from here on foot, walk back to the hotel with the group leader, or take the Duval Loop (the city's free bus that can drop you near the hotel). If you wish to take the Duval Loop, your group leader can show you how.
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
Location:
Key West Old Town
Meals:
B
Stay:
The Marker
Activity Note
Walking up to 1.5 miles today on paved sidewalks. 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 from an expert about marine archaeology and sea 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, Eco Discovery Center
Location:
Key West Old Town
Meals:
B,L,D
Stay:
The Marker
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 between destinations.
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 Florida Keys Eco-Discovery Center. Here we will learn about the area's different ecosystems, creatures, history, and conservation efforts. We will receive a presentation from a docent before having the opportunity to explore the natural history museum's more than 6,000 square feet of interactive exhibits.
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
Location:
Key West Old Town
Meals:
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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Please Note:
This program has itinerary variations on certain dates.
Dec 07, 2025 - Dec 12, 2025
Nov 02, 2025 - Nov 07, 2025
Nov 16, 2025 - Nov 21, 2025
Dec 07, 2025 - Dec 12, 2025
Jan 04, 2026 - Jan 09, 2026
Feb 01, 2026 - Feb 06, 2026
Feb 22, 2026 - Feb 27, 2026
Mar 08, 2026 - Mar 13, 2026
Nov 15, 2026 - Nov 20, 2026
Dec 06, 2026 - Dec 11, 2026
Dec 7 - Dec 12, 2025 Itinerary Differences:
Accommodations are at The Marker Key West
