J Magazine Winter 2019
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BOB SELF<br />
As thousands<br />
of Downtown<br />
workers head<br />
to their offices<br />
for the day,<br />
Gary Sass is<br />
imparting<br />
subterranean<br />
history lessons<br />
in Jacksonville’s<br />
urban core<br />
“I’M A MAN OF PROPS,”<br />
said Gary Sass, and that much is readily<br />
apparent. At his feet sits a black-and-white<br />
canvas tote bag stuffed with the visual aids<br />
he employed while leading a tour of Downtown<br />
churches earlier that day.<br />
“When people ask me a question, I can<br />
physically show them a prop on the tour. It’s<br />
a style that I have.”<br />
It was a Monday in mid-September,<br />
when we met, plowing through bagels and<br />
juice before settling down for a bull session<br />
that lasted nearly two hours. As the owner<br />
of Ad Lib Luxury Tours, Sass has become<br />
something of a local icon, a fixture in the<br />
urban core who knows this city as well as<br />
almost anyone alive today.<br />
Sass was born in Kingston, N.Y. in late<br />
February of 1963, cultivating a love for history<br />
from an early age.<br />
“It was the first capital of New York<br />
State,” he said, “and then the British<br />
burned it in 1777, and the capital moved<br />
to Albany.”<br />
He attended SUNY-Potsdam in the early<br />
‘80s, majoring in computer science. That<br />
work took him all over the U.S. and Europe,<br />
paying the bills while helping him build his<br />
archive of historical data.<br />
“I was a little bit of a confirmed bachelor,<br />
and then I met my wife while I was working<br />
in London for a year.” Ironically or not, they<br />
met on a walking tour.<br />
After the birth of his second child 15<br />
years ago, Sass and his wife decided to scale<br />
back on the constant moving that went with<br />
his IT career.<br />
“So we went on a six-month study of the<br />
perfect place to live in the United States.<br />
My wife went to a website; she answered<br />
250 questions and up popped Jacksonville,<br />
Florida as her perfect place to live. So we<br />
started researching Jacksonville, and other<br />
areas, and Jacksonville came up No. 1,<br />
based on all the criteria that was important<br />
to us, from cost of living to proximity to<br />
the beach, weather, all different types of<br />
factors.”<br />
Sass and his wife were just two of the<br />
thousands of people who’ve moved to Jacksonville<br />
over the past decade, but among<br />
them all, it’s likely that no one else put more<br />
thought into the decision.<br />
Once they’d picked their city, they<br />
narrowed their focus to specific neighborhoods.<br />
“We ended up on the border of St.<br />
Johns and Duval County,” said Sass, “in<br />
a community called Walden Chase. That<br />
community became Nocatee.”<br />
He continued in the IT biz for a while,<br />
but was often rejected for being overqualified,<br />
and that quickly pushed him to finally<br />
pursue his passion full-time.<br />
“I went two months without a job,” he<br />
said, “and then I said to my wife, ‘Well, let’s<br />
take this as a sign that we’re supposed to<br />
start our own company.’”<br />
He had a couple ideas, but the tours that<br />
resonated.<br />
“Nobody is doing personalized tours,<br />
and nobody is doing Jacksonville. In<br />
St. Augustine, it was just the trains and<br />
trolleys,” he said. They had run such tours<br />
successfully in a number of cities previously,<br />
around the world, so they decided to<br />
reboot the gimmick here, basically starting<br />
from scratch.<br />
“We decided that we would become the<br />
local experts.”<br />
FROM THE MOMENT OF<br />
finalizing their decision, it was about<br />
three weeks before their first tours. Sass<br />
had started researching the area from the<br />
moment he arrived, leaning heavily on the<br />
local library and the Jacksonville Historical<br />
Society.<br />
“I’m a pretty quick study,” he said. “I<br />
became friends with the people who ran<br />
the archives,” folks like Wayne Wood and<br />
Emily Lisska. “They became some of my first<br />
friends here,” he said.<br />
He spends as much time researching<br />
his subject matter as he does on the actual<br />
tours, if not more. This has made Sass, a relative<br />
newcomer, an expert on local history.<br />
He counts local legends like Wayne Wood<br />
and Tim Gilmore as friends.<br />
Now 15 years into the venture, business<br />
is booming with Sass becoming something<br />
of a local icon.<br />
“We are definitely slower in the summertime,”<br />
he said. “The reason being is that<br />
locals don’t necessarily want to do tours in<br />
the heat, and the visitors want to go to the<br />
beach. The times when we’re busiest are<br />
the spring and the fall, when the weather is<br />
better for people to do activities. Christmas<br />
time, I’m not that busy, unless it’s a theme<br />
tour.”<br />
Much of the tour activity is conducted on<br />
foot, but he also has access to a small fleet to<br />
ferry customers.<br />
“I’m a transportation company,” he said.<br />
“I have one vehicle, an eight-person luxury<br />
van; it’s built out like a limousine on the inside.<br />
I realized that for a small group, it’s too<br />
expensive to rent out a vehicle and driver<br />
and a tour guide, so I just do it myself. This<br />
works really well for the higher-end tours.”<br />
Sass works closely with the hotels in<br />
Jacksonville, St. Augustine, Amelia Island<br />
and Ponte Vedra. “I’m used as kind of a<br />
resource by salespeople when they’re selling<br />
the area.” He’ll even [Continued on page 96]<br />
WINTER <strong>2019</strong> | J MAGAZINE 85