J Magazine Winter 2019

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