Historical Tour Guide Cliff Shields

Cliff Shields is a historical tour guide and reenactor with Tour St. Augustine, who portrays Henry Flagler, a railroad magnate of the Gilded Age. A St. Augustine resident since 2014, Cliff fell in love with…

Cliff Shields is a historical tour guide and reenactor with Tour St. Augustine, who portrays Henry Flagler, a railroad magnate of the Gilded Age. A St. Augustine resident since 2014, Cliff fell in love with the city and devoted his time to learning about its history and that of the people who have influenced it over hundreds of years.


What is your favorite thing about St. Augustine and St. Johns County?

I enjoy the history the city has to offer being the oldest city in America. The city is not overcrowded with full-time residences, but I love the fact the tourism is so plentiful. Saint Augustine is a picture-perfect storybook location to visit and live.


What led you to become a St. Augustine history buff, and an expert on Gilded Age Mogul Henry Flagler?

I retired from 31 years in the hotel/resort industry and 15 years from the National Cemetery Administration, an agency within the Veterans Administration. After a couple of years of retirement and just “relaxing on my time” I decided I wanted to do something fun and part-time to fill a void in my life. I saw the tourism in St. Augustine and wanted to be a part of the “action.” I simply just walked into the office of Tour Saint Augustine on Granada Street and introduced myself and asked what I needed to do in becoming a tour guide. I was given an opportunity, after interviewing and being hired as a tour guide for field trip students. I was then asked if I wanted to do adult bus tours as a character in history. Having an extensive background in the hotel/resort industry I felt Henry Flagler was an excellent character to portray … and as Paul Harvey used to say, “and now you know the rest of the story.”


How has reenacting historical figures and events affected your life?

Stepping onto a tour bus with adults as Henry Flagler turns a lot of heads. I love staying in first person as I do and watch the faces of people and the comments they make all while giving a 452-year history lesson on St. Augustine. It gives me great satisfaction at the end of the tour to get a round of applause, handshakes, and many photo opportunities. I may never see them again but I know I have made many friends, memories and a good impression. I look forward to being called upon as Henry Flagler in the community. The bottom line: it has filled my retirement years with fun and excitement.


What is your favorite aspect of reenacting?

My favorite parts are the looks and stares you get when entering a building, area or tour bus. People who know Henry Flagler call out my name and generally want to take a picture, shake my hand or just ask me questions.


How have you seen St. Augustine change/grow for the better?

I was in St. Augustine in 1958 as a 9-year-old. I returned in 2013 for the first time with the National Cemetery as the Director of the Jacksonville and St. Augustine National Cemeteries. I chose to retire December 31, 2014. I have now seen St. Augustine in a whole different perspective. Growth in the tourism industry from 1958 to 2017 is extraordinary. I guess I can say it is the “Tale of Two Cities” in growth and excitement. The Old Town Historical District is like going back in time but mixed with the modern lifestyle in the suburbs. It is the best of both worlds.


What is your favorite place in St. Johns County? Why?

Why, of course, that would be St. Augustine. It is the history, mystery, mayhem, ghosts and magic that make St. Augustine my favorite place and I get to work and live here and share all of that with the tourists.


What is your favorite Henry Flagler story and why?

My favorite Henry Flagler stories are his rise from rags to riches and launching himself into the Gilded Age with Standard Oil, John D. Rockefeller, and the Ponce de Leon and Alacazar Hotels. I always start out with that story just in case there is someone in the crowd that has no idea who Henry Flagler was, and there is always one. Everyone can identify with Standard Oil and the Rockefeller family. It is always a hoot to talk about his three wives, especially Ida Alice.


Behind the scenes with Cliff Shields