Brad Bertelli: Author, Historian, Tour Guide

Jerry Wilkinson and Brad Bertelli
Jerry Wilkinson and Brad Bertelli

No offense to Chef Lupe and Michelle Ledesma, who have employed me at Islamorada’s Lazy Days Restaurant for nearly a decade, but I am trading in my server’s apron to pursue my professional passions.

I am sorry, but I will no longer be asking the important question, “Blue cheese, Ranch, or Tomato Basil?” Instead, I will be spending more nights with my beautiful wife Michelle. Also, I will be able to spend more time on my other two passions: writing and Florida Keys history.

It is possible to pinpoint exactly when and where these changes in my life first began to percolate. It was the day I sent an email to Jerry Wilkinson, a man I had never met. Mr. Wilkinson’s response reinforced my burgeoning interest in the local history and ultimately a friendship developed; it redefined my life and for that, for Jerry, I will forever be grateful. My hope, my plan, is to grow into his historically grand shoes.

To be clear, in no way do I consider myself anywhere near the class of Mr. Wilkinson. The man has spent decades studying these islands, colleting every document, picture, and book he could get his hands on. The truth is that more has happened on this skinny-as-bones string of islands than would immediately appear to be the case, and for as much as I study and write about the Keys, there is still so much to learn.

I have been studying the Florida Keys and the Florida Reef for five years or maybe six, tops — a mere drop in the bucket compared to the time Jerry has put in. However, if there was ever someone who had the thirst and the passion to step into Mr. Wilkinson’s shoes, I am the guy who is going to invest decades of study to get the job done. The history of the Florida Keys and the Upper Keys in particular has become my new full time job.

My plan is three-pronged. I will keep writing. In addition to my column, I am working on a series of books about the Upper Keys. The most immediate release will be the Arcadia book, Images of America: Islamorada due on bookshelves Feb. 10. Like the book Key Largo, Islamorada was co-authored by my mentor Jerry Wilkinson.

Among other projects, I am working on a book about Indian Key, my favorite island in the whole of the coconut chain. However, I will be doing more than writing about the history of the Florida Keys. To that point, I have been working as a consultant with the Florida Keys History and Discovery Foundation ( The Foundation’s desire, like my own, is to document and preserve the history of the Florida Keys and that of the Upper Keys in particular. Trust me when I say there are exciting plans in the making.

In another effort to promote the history of the Upper Keys, the Historic Upper Keys Walking Tour Company ( has been developed. “Join local author and historian Brad Bertelli as he strolls past some of the most historic scenery the Upper Keys have to offer.”

Two tours are currently offered: the Islamorada Hurricane Tour and the Historic Downtown Tavernier Tour. The 40-minute Islamorada tour starts at the Hurricane Monument and explores a fascinating stretch of the Old Highway that is particularly festooned with historical nuggets. Tours meet every Thursday at 10 a.m. or they can be arranged by appointment. The cost is $10.

The Tavernier tour is currently arranged by appointment, lasts approximately one hour, and cost $16. How pineapples and hurricanes helped to define the turn of the century community are explored, as well as one of Tavernier’s earliest subdivisions, Ollywood. Also included on the tour is the story of Captain Ben Baker, the King of the Florida Wreckers, who first brought pineapples to the island of Key Largo. The tour ends in front of the Tavernier Hotel, a building originally constructed as a movie theater.

I am nervous walking away from the restaurant. It will be an adjustment not having a pocketful of tips at the end of the night. In the dozen years I have lived in the Florida Keys, I have never once had to use my debit card. Frankly, I don’t know the pin number to the account. In any case, hopefully there won’t be too many surprises in the months to come. I will just stick to the plan and concentrate on being Brad Bertelli: author, historian, tour guide. To wish me luck or book a tour call: (305) 395-9889.

Brad Bertelli is a published author of four books on Florida and Florida Keys history. His column will appear every other week in The Reporter. Reach Brad with comments and questions at