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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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Select your type of room
Price will update based on selection
Prices displayed below are based on per person,doubleoccupancy.
DATES & starting prices
PRICES
Jan 14 - Jan 19, 2024
Starting at
3,149
Filling Fast!
Jan 28 - Feb 2, 2024
Starting at
3,149
Feb 11 - Feb 16, 2024
Starting at
3,599
Feb 25 - Mar 1, 2024
Starting at
3,599
Dec 1 - Dec 6, 2024
Starting at
2,399
DATES & starting prices
PRICES
Jan 14 - Jan 19, 2024
Starting at
4,599
Jan 28 - Feb 2, 2024
Starting at
4,599
Feb 11 - Feb 16, 2024
Starting at
5,419
Feb 25 - Mar 1, 2024
Starting at
5,419
Filling Fast!
Dec 1 - Dec 6, 2024
Starting at
3,269

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.

Best of all, you’ll…

  • 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 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 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 Lynn Wanous
Lynn Wanous View biography
Lynn Wanous and her family sailed into the Florida Keys on their sailboat in 1990s. Lynn has fully embraced the island culture and is now a "fresh water conch," a term for long-time non-native residents of Key West. She worked at Edward Jones Financial Services and won the prestigious Spirit of Caring Award, given annually to only one employee in the entire company. Lynn has been leading Road Scholar Key West groups since 2018.
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.
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.
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.
Key West: History of an Island of Dreams
by Maureen Ogle
Parrotheads, Hemingway aficionados, and sun worshippers 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.
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.
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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!






Important registration tip:
If you want to attend the live lecture, please do not wait until the last minute to enroll.
If you enroll after a lecture is complete, we’ll send you a recording of the event.