KEY WEST CITY TOUR FIELD GUIDE
A 90‑Minute Literary Stroll Through Old Town Key West’s Writerly Crossroads
A guided walking tour of downtown Key West that visits the former homes and favorite haunts of Tennessee Williams, Shel Silverstein, Elizabeth Bishop and Robert Frost—useful for travelers wanting a concise, authoritative orientation to the island’s literary history.
A 90‑Minute Literary Stroll Through Old Town Key West’s Writerly Crossroads.
Join the Old Town Literary Walking Tour to move through downtown Key West with a guide who illuminates the writers who called the island home. Inspired by David A. Kaufelt’s original route, the tour visits former homes and favorite haunts—bringing to life stories about Tennessee Williams, Shel Silverstein, Elizabeth Bishop, Robert Frost and lesser‑known local talent—and lasts about 90 minutes. Tours begin in front of the Monroe County Public Library at 700 Fleming Street; participants are asked to arrive on time and wear comfortable shoes.
Highlights
Outing Highlights
Stops Tied to Major 20th‑Century Poets and Playwrights
The tour points out the former homes and favorite haunts associated with internationally known writers—an on‑the‑ground way to connect place with the pages of mid‑century American literature.
A Compact Walk Through Downtown Old Town
Designed to be completed in roughly an hour and a half, the route threads through downtown Key West, pausing at houses, haunts and lesser‑known local sites that shaped writers’ lives and work.
Beyond the Names: Tales of Island Talent
Alongside the big names, the guide highlights stories of local writers and community context, offering a richer picture of Key West’s literary life beyond headline authors.
What the day feels like
What the Walk Feels Like
Expect a paced, interpretive stroll through Old Town: the guide pauses at former residences and neighborhood haunts, layers in anecdotes about writers’ lives and work, and moves on—covering the essentials in about 90 minutes from a meeting point at the public library.
THE LEGENDS
Stops Tied to Major 20th‑Century Poets and Playwrights
The tour points out the former homes and favorite haunts associated with internationally known writers—an on‑the‑ground way to connect place with the pages of mid‑century American literature.
THE ROUTE
A Compact Walk Through Downtown Old Town
Designed to be completed in roughly an hour and a half, the route threads through downtown Key West, pausing at houses, haunts and lesser‑known local sites that shaped writers’ lives and work.
THE LOCAL THREAD
Beyond the Names: Tales of Island Talent
Alongside the big names, the guide highlights stories of local writers and community context, offering a richer picture of Key West’s literary life beyond headline authors.
Suitability
Who it's for
Who gets the most from this walk (and what administrative details to know).
Practical planner
Details to review before reserving
Wear comfortable shoes suitable for walking; plan to arrive at the meeting point on time.
Check in at the meeting point in front of the Monroe County Public Library and have any ID ready if you qualify for educator or student pricing.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long is the Old Town Literary Walking Tour?
The tour lasts approximately 90 minutes.
When does the tour run?
Tours are offered on Sunday and Wednesday.
Where do we meet for the tour?
Tours commence in front of the Monroe County Public Library, 700 Fleming Street (between Elizabeth and William Streets) in Key West.
What are the admission rates and are there discounts?
General admission is $30; discounted rates are available for teachers & librarians and for students.
Do teachers, librarians or students need ID?
Yes—teachers, librarians and students must present valid ID at check‑in to receive discounted admission.
Is there any specific clothing or footwear recommended?
Participants are asked to wear comfortable shoes appropriate for a walking tour and to be on time at the meeting point.