Local tour guide brings Downtown history alive

Gary Sass
Gary Sass

Any given week, you’ll find Andrew Jackson walking the streets of Downtown – well, Gary Sass dressed as Andrew Jackson, that is.

Sass, a local history buff and Downtown advocate, is entering his fourth year as guide of the Downtown Jacksonville “Top to Bottom” Walking Tour, now available both Tuesday and Thursday mornings at 10 a.m. After eight years of providing North Florida tours from Fernandina to Palm Coast, Sass’s company, AdLib Luxury Tours & Transportation, now conducts more Jacksonville-area tours than St. Augustine tours. And, no surprise, the most popular tour destination is Downtown Jacksonville.

We recently chatted with Gary about why he loves showcasing Downtown Jacksonville and sharing its best historic stories.

Where are you from originally, and what brought you to Jacksonville?

My family and I moved here from upstate New York. Our fascination with Jacksonville started after taking an online quiz from Jacksonville popped up as our No. 1 place to live. We decided to move here first, and then we would create the perfect job. The result was AdLib Luxury Tours & Transportation.

What is your background? Did you learn to give tours, or are you self-taught?

My degree is in computer science, and I worked for 20 years in software development and services for companies such as IBM. My wife and I both took many tours around the world – we even met on a walking tour of London. We were surprised no one was doing tours of Jacksonville or offering personalized tours in North Florida. So we developed our own style, a luxury tour with a flexible itinerary, that would match the first-class service expected at a top resort hotel.

At the Laura Street Trio.
At the Laura Street Trio.

How did the idea for the “Top To Bottom” tour come about?

Visit Jacksonville asked if we could take a travel writer on a walking tour. The travel writer ended up writing about this great walking tour of Downtown going in and out of buildings. I did not realize how good a product we had until she wrote about it! We decided to create the Jacksonville Walking Tour program about three years ago, and our first offering was the Tuesday 10 a.m. “Top to Bottom” tour.

What does your tour feature?

We feature the “top” of Jacksonville with skyline views from the tallest building and the secret underground tunnels that make up the “bottom.” There are other stops on the tour including The Florida Theatre, The Carling, Greenleaf & Crosby building and the Wells Fargo Center. Each stop features a unique historical or cultural aspect of Jacksonville. The new Thursday “Top to Bottom” version includes a behind the scenes look at the Jacksonville Symphony.

What types of groups do you typically get on your tour?

The majority of the people on tour are locals. Some of our tour guests work Downtown, and some are traveling to Downtown just for the tour. People really enjoy learning about their city. The number of tourist attendees is growing every week as the community realizes we are a destination. Often groups call to reserve a day and time for a private tour, and we’ve customized the tour for school groups and company team-building.

What part of the tour do your guests typically enjoy most?

The tour is designed to strike a responsive chord with everyone given all the cultural touches. However, it is fun to hear the “oohs and ahhs” as you walk through the dark tunnel. Everyone loves to take photos of the underground bank vault and old safe-deposit boxes.

Inside the bank vault.
Inside the bank vault.

What are your goals with these tours?

Our goal is to deliver the most entertaining tour while showing off the best of Downtown. We enjoy sharing the local history and culture by telling our Jacksonville story through many props. We are also demonstrating every week that Downtown is a safe destination and an awesome place to live, work and play.

What do you love most about Downtown Jacksonville?

From a business perspective, the support we get from Visit Jacksonville, Jacksonville Landing, Downtown Vision, Florida Theatre, Skyline Café, Southlight Gallery, the Carling, 121 Atlantic Place, Wells Fargo, Jacksonville Symphony and others are very key and a win/win for all Downtown stakeholders.

From a personal perspective, I really enjoy the variety of restaurants and events.

Where do you see Downtown tours in the future?

As Downtown grows as a destination so will the variety of tours we offer. We have developed many walking, driving and river tours, so it will be fun to roll them out as people discover Downtown. We’re launching an 8 p.m. Friday “River City Haunts” ghost tour in October, where tour-takers will encounter local ghosts while finding out why they are haunting the city.

To learn more about Sass’s “Top to Bottom” Tour, visit his company’s website. Hospitality employees at hotels are invited check out the “Top to Bottom” tour for free. All “Top to Bottom” tours meet at the Jacksonville Landing escalators at 10 a.m. Tuesdays and Thursdays. Call 904-827-1845 or email to reserve.