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Florida

Key West at a Slower Pace: Living on Island Time

Program No. 21797RJ
Find out what makes Key West such a unique city as you stroll its vibrant streets, discovering its heritage, culture, world-class museums and the true spirit of island life.

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At a Glance

Don’t let the quaint, small-town façade fool you — there’s a lot more to Key West than meets the eye. Discover all its hidden treasures at an easy pace befitting this laid-back island city. Navigate by trolley to experience its rich history and the unique pace of life on “island time.” Appreciate the blend of Victorian, Bahaman and New England architecture in its iconic “conch houses.” Hear tales of ships and shipwrecks and walk in the footsteps of larger-than-life figures like Hemingway and President Truman. Share the spirit of the island with artists, divers, gardeners, historians, musicians, oceanographers and other experts who reveal the city through the eyes of Key West natives.
Activity Level
On Your Feet
Walking up to one mile on even terrain.

What You'll Learn

  • Go inside the structure that gave birth to Key West’s historical restoration movement, the Audubon House, where you can see 28 first-edition works by James Audubon.
  • With a docent, navigate the Custom House Museum, a living link to Key West’s historic past and home to art and artifacts that tell the story of this island town.
  • Learn about life in Key West when Ernest Hemingway and President Harry Truman were residents during explorations of the Hemingway House and Truman's Little White House.

General Notes

You may be interested in a more active version of this program, "Signature City Key West" (#20902).
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 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.
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: 3:00-5:00 p.m. After you have your room assignment, come over to the Road Scholar desk in the lobby to pick up your arrival packet containing your up-to-date schedule, and to confirm the time of dinner and the orientation session. During orientation, 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. The remainder of the evening will be at leisure. Settle in, relax, and prepare for the day ahead. On our trip we will learn from our knowledgeable Group Leader along with a series of local experts who will give lectures and lead field trips. Program-related travel and transfers will be via a trolley transportation unless noted otherwise. Meals will feature local cuisine in a variety of settings. 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.

DAY
2
Boat Cruise, Trolley Tour, Stories of the Deep
Key West Old Town
B,L,D
Opal Key Resort & Marina

Activity note: Walking up to 1 mile to travel to our destinations, with breaks in between. Walking on sidewalks. Getting on/off a trolley which has three steps. Remember to wear comfortable shoes, use sunscreen, and wear a hat.

Breakfast: At the hotel.

Morning: We will set out to enjoy Key West by boat, learning about its shorelines and history on this morning cruise.

Lunch: At a local restaurant with the group.

Afternoon: This afternoon, we’ll experience Key West by private trolley with commentary from our driver. We will hear stories from Key West’s most famous – and infamous – residents and learn what draws so many people to this unique destination. While you’re out and about, take note of some of the things you’d like to see and do in Key West during your free time this week.

Dinner: At a local restaurant.

Evening: Back at the hotel, we will wrap up our first day meeting and hearing from a local deep sea diver who will delight us with tales of his many years of fishing and diving in these waters.

DAY
3
Hemingway House, Tennessee Williams, San Carlos Institute
Key West Old Town
B,L,D
Opal Key Resort & Marina

Activity note: Getting on/off a trolley which has three steps. Climbing a flight of stairs at Hemingway House. Walking up to 1.5 mile with breaks in between. Remember to wear comfortable shoes, use sunscreen, and wear a hat.

Breakfast: At the hotel.

Morning: This morning, via trolley ride, we will go on a literary journey of Key West starting with the Hemingway House. 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 with the group.

Afternoon: We will walk to the nearby San Carlos Institute, a cultural hub for Key West’s Cuban diaspora since 1871. With donations from tobacco farmers in Cuba, the Institute served as the epicenter for the Cuban independence movement from Spain and as a school for exiles with instruction in both English and Spanish – one of the first schools to do so in the U.S. During our visit, we will delve more into the San Carlos Institute’s rich and storied past and learn about its present-day functions with a short introductory film followed by an exploration of the Institute’s current site and an expert-led lecture.

Dinner: At a local restaurant.

Evening: At leisure.

DAY
4
Audubon Lecture & House, Custom House, Free Time
Key West Old Town
B
Opal Key Resort & Marina

Activity note: Walking up to .5 miles on paved sidewalks. Standing up to 1 hour; climbing a flight of stairs at the Audubon House. Walking and other free time activities according to personal choice.

Breakfast: At the hotel.

Morning: This morning at the hotel, we'll 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’ll go on a docent-led visit 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. We’ll end our morning with a visit 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.

Lunch: On your own to sample the daytime local fare.

Afternoon: Free time. Your group leader will be happy to make suggestions. One idea before dinner is attending the daily 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.

Dinner: On your own this evening to explore and sample the town’s numerous dining options.

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.

DAY
5
Little White House, Mel Fisher
Key West Old Town
B,L,D
Opal Key Resort & Marina

Activity note: Walking up to 2 miles throughout the day with breaks in between; standing at sites on docent-led trips.

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 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, Independence, Missouri.

Lunch: At a local restaurant.

Afternoon: Next, we will visit the Mel Fisher Maritime Museum where we will learn from a docent 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 to see the conservation lab. If you have not already, this evening is your last opportunity to attend 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.

Dinner: At a restaurant near Mallory Square.

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.

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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