A lifelong Conch falls even more in love with Key West



Lace up your sneakers and lather on the sunscreen, because it’s time to join fifth-generation Conch Monroe Holloway on a journey like no other in the Florida Keys.

A Key West native, Holloway leads walking tours under the pseudonym of Monroe Hemingway, paying homage to his favorite Key West leading citizen, a role he also takes to heart.

His Southernmost Historical Walking Tours offer a way to learn about the history of our beautiful island while burning the calories all those margaritas have packed on. Early risers can set out at 9 a.m., while tourgoers who would rather not schlep around town before they’ve had a proper breakfast cocktail canbooka1p.m.departure.

All tours are an hour long and begin near the historic Southernmost House Hotel (1400 Duval St.), an island landmark. From there, the tour heads toward Truman Avenue as Holloway shares a wide variety of historical facts about Cayo Hueso.

After the tour, guests are invited to Ana’s Cuban Café (corner of Simonton and South streets) for their choice of flan, Key lime pie or conch ceviche (a local favorite).



Holloway started his Southernmost Historical Walking Tours because of his passion for history and desire to bring it back to life. He strongly believes there is a lack of Key West history and wanted to create a business to share the voluminous research he has conducted.

His vision is to take people into the weeds of Key West, where they can discover a side of the town not possible to experience from a vehicle. He has spent countless hours researching at the local library, scouring websites and interviewing Key West legends to build up his knowledge of the island’s history and people from 1871-1920.

Tourgoers are encouraged to ask questions and photograph the various landmarks. Each intimate group learns about the quirky architecture on the island, specifically the history of the Gato building and the Southernmost House, including how they got their names.



At the end of the hour, tourgoers are ready for the Key West version of “Jeopardy!” or for that phone-a-friend call that might come in from a pal who makes it onto “Who Wants to be a Millionaire: Key West Edition.”

Who knew that cigars from Key West were once a sought-after commodity? Not me. Or that the Avalon House was once called the Cuban Club? I didn’t, either. This is precisely why I booked a Southernmost Historical Walking Tour.

Holloway — who, by the way, is not only easy on the eyes, but also on the ears — educated me from the start with information I never knew about my hometown. Growing up in Key West, I have my fair share of fun facts and stories passed down from my grandma, but he put me to shame.

Holloway is a walking encyclopedia of Key West knowledge. I love how he turns facts into stories to help make things more relatable. He paints a picture like no other guide on the island, and it’s a masterful painting.

We started our private tour on a gorgeous February morning. I’ll be the first to admit that I am lazy and prefer – y, driving every chance I can get, so of course I was hesitant to take the tour in the first place.



I am not one to sweat and be bothered with the heat, but after chugging an iced coffee, I gave in. And boy, am I glad I did.d.

Holloway kept theh pace as hhe guidedid d me from street to street. We stopped in front of several old Conch houses and he explained the architecture. Even though I grew up in a Conch house built by my late grandfather, Roy Potter, I didn’t know the history behind these special designs — until Holloway told me.

You can tell just how eager and passionate he is about his new venture. When he speaks, the excitement rushes out of his voice and into every story he tells. Luckily for me, he kept me laughing and walking so I didn’t have time to complain about the heat.

I fell in love with Key West a little more that morning and became even more proud to call this little island home. Holloway made me feel smarter than my senior high school self (and if you knew your girl back then, she thought she was the smartest).

As the tour came to an end, we parked ourseves on a bench at Ana’s Cuban Café.


Naturally, I ordered the Key lime pie as a reward to myself for keeping up (and sweating it out) on the tour. It was the perfect way to end an already productive and beautiful morning. And after a morning absorbing all of Monroe’s informative stories, the stop at Ana’s is a great way for tourgoers to unwind, reconnect and regroup, all while tasting a piece of paradise.

Considering how much I learned about the island I’ve called home my entire life, I highly recommend Southernmost Historical Walking Tours for anyone, visitors and longtime locals alike. So gather some friends and give Holloway a call. I promise you won’t regret it.

Tickets are $25 and well worth it for the most interesting and in-depth look at Key West from a local storyteller’s perspective. Just show up at the starting point a bit before 9 a.m. or 1 p.m., or book online at www.travelthekeys.com. ¦

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