old Town Trolley Tours quiz challenge

Look who stopped by!

January 8th, 2015

No sooner do we put up our new countdown clock than St. Augustine’s founder, Pedro Menendez, pops by to check on the date. Seems he’s needs a reminder to the big day.  We guess when you are 496 years old, your memory starts to fade a bit.450th Countdown Clock  Pedro

The Countdown Begins!

January 2nd, 2015

2015 will mark the 450 anniversary of the founding of the city of St. Augustine by Pedro Menendez de Avilies.  As part of the city’s celebrations, a countdown clock will be installed at the visitors center so residents and visitors alike can keep track of the big day!  Old Town Trolley tours of St. Augustine sponsored the clock and our GM Dave Chatterton can wait to see it installed.

General Manager David Chatterton with the countdown clock.

General Manager David Chatterton with the countdown clock.

Meet Lauren Sheldon

November 18th, 2014


Lauren Sheldon

Lauren Sheldon



I am originally from North Andover, Massachusetts which is just north of Boston. I moved to Washington, DC on a whim in May of 2013 when I decided it was time to get out of New England. I graduated from the University of New Hampshire with a dual degree in Theater & Politics (because I figure they are the same thing ;) . Before working for Old Town Trolley, I helped to start the historic walking tour company, Cambridge Historical Tours on the Harvard University campus. There I portrayed Margaret Fuller, one of America’s first women to publicly speak out for women’s rights and education. Theater is my greatest passion and I often get caught singing show tunes at my desk. I am optimistic, upbeat, and a very positive person.

Which living person do you most admire?
My mom, Gail Sheldon, is my hero. She is the most supportive, loving, and strong woman I know. I aspire to be just like her every day.

What is your favorite vacation spot?
I love traveling to places where I can be immersed in a new culture, language, or learn something new. I would love to explore more of Central America, Southern Europe, or Africa.

What or who is the greatest love of your life?
Theater is my greatest passion in life. I was introduced to the movie Grease on my 8th birthday and I’ve been singing and performing ever since.

If there is one place you would like to live besides your current city, where would it be?
There are so many places I would like to live or visit throughout my lifetime, but at this point I would love to go to Chicago. It isn’t as big as New York, it is on the water, and it has a great theater scene.

If you could choose one reality TV show to be on, what would it be?
Survivor. My family and I still watch it religiously each week. And even if I weren’t the contestant and my sister Colleen went out there instead, I would still be her “loved one” because in a challenge she knows I would eat a bug for her.

Meet Tim Conway

November 15th, 2014
Tim Conway

Tim Conway

I was born and raised in N. E. Ohio, I had a great life growing up on the river and then the lake. I had a great childhood! My parents were both professionals, a teacher and a dentist. They both grew up during the depression with a love of life, family and fun. They taught my sister, brother and I that family is FIRST. I live that to this day.
My life after “leaving home” was about wrestling in college at Kent State and at Western State in Colorado. I was good but not great. After college I joined the Navy, had great a great time and got to see a lot of the world. That’s when I became a Yankee! I met and fell in love with Rhonda, a southern girl, and stayed.
When I was discharged from the Navy I began my sales career. I sold everything from boats and windsurfers to marine supplies during my 25 years in industrial and commercial sales. I’ve spent as much time with my boys and their school and athletics as I could. They’re great! I could go on and on about them and especially Rhonda but I won’t.

Which living person do you most admire?
If my father were still alive it would be him! He was the smartest, most fun to be around, hardworking, with an absolute love life and family. Since he passed it has to be my wife Rhonda. She has always been there for me and the boys, and has persevered through cancer and her mother’s death with grace and tenacity. She does her best to keep me in line! She has to be a saint to put up with me for over 32 years!

Who or what is the greatest love of your life?
Easy peasy, my wife Rhonda.

If there was one place you would like to live besides your current city, where would it be?
Two places, a winter home in Hope Town, Bahamas and a summer home on a lake up north.

What is your favorite occupation?
SALES, I love what I do. I’m pretty good at it. There are so many opportunities! Every business starts with someone selling something.

Who are your favorite writers?
Lee Child, James Patterson and Milton Freedman

Bella Joins our Fleet!

November 7th, 2014

Introducing “Bella”, our second wedding trolley we’ve added to our fleet, joining our other wedding trolley “Felicity”. Our wedding business has been growing year-over-year at about 15% above last year’s numbers. During the peak wedding months between April-September, our wedding trolley “Felicity” is often booked, sometimes up to a year in advance. We have missed out on additional wedding transportation business due to the lack of our special wedding trolleys. “Bella”, was originally one of our red Balboa Park shuttle trolleys that provided free service by the City of San Diego. The city purchased their own trams for the park shuttle service resulting in three extras trolleys for us. With the wedding peak season fast approaching, our maintenance crew worked feverishly transforming the red trolley into our new pristine “Bella”. With just days away from “Bella’s” first wedding, she was christened “Bella”.

Meet Rich Montaudo

November 5th, 2014
Rich Montaudo, Head Conductor, Savannah

Rich Montaudo, Head Conductor, Savannah

Rich Montaudo is our Head Conductor in Savannah. We thought it would be fun to put him on the hot seat with a few questions and answers.

Rich was born in Huntington, WV and is a proud military vet. Before joining Old Town Trolley, Rich was in the EMS field, either on an ambulance or in the 911 call center. He met his beautiful wife Renee, when she was a student of mine in an Advanced BTLS for Health Care professionals class he was teaching. Theyhave two great kids, Austin a sophomore at Armstrong State University and Madison a junior in high school.

What is your idea of perfect happiness?
Riding Bobbi Sue (my Harley Road King Classic) with my wife, destination unknown.

What is your greatest fear?
Failure as a husband and father….. failure in general.

Which talent would you most like to have?
To play a musical instrument.

What is your most treasured possession?
Simple my Harley Davidson Road King Classic.

What three things will you always find in my refrigerator?
Eggs, milk and habanero hot sauces.

Baking for Breast Cancer

October 28th, 2014

Each October our amazing CAST at Old Town Trolley Tours of San Diego’s raised money for Breast Cancer Awareness. Through bake sales, yard sales, and tip donations, these amazing men and women raise over $5000 for the University of California – San Diego Moors Cancer Center. This is their fourth year and their efforts and enthusiasm get bigger each year!

Old Town Trolley Tours of San Diego baking for a good cause.

Old Town Trolley Tours of San Diego baking for a good cause.

Meet Darlin Deb

October 23rd, 2014

OTT Bos Cast Spot Darling Deb

I was actually born right in the city of Boston….just a few years ago… and grew up in the very historic town of Concord, Massachusetts, home of the American Revolution, and many famous writers and philosophers like Thoreau, Alcott and Emerson. History and visitors from all over the world were just a part of growing up in my town so I feel right at home working in OTT Boston. Every Patriots’ Day in April my family and I still attend the annual parade and watch the Minutemen and British militia meet at the Old North Bridge on the Concord River.

After high school I went off to college in Maine…Colby College..where I majored in French. Junior year was spent studying in France in Paris and in Normandy where I lived with a wonderful French family. While I was there, my friends and I traveled as much as possible all over France and anywhere else we could afford. One very special memory was our trip from Paris to Istanbul and Athens on the original Orient Express train, 4 days in the 3rd class compartment! My love of travel and languages was really ignited that year and they continue to be a very important part of my life. After college I lived in California and in Boston while I tried out some different jobs and took courses in education to get a teaching certificate. My career began with teaching French classes in a middle school and later taking courses in Spanish and French for a Masters in both languages. After many years of teaching both French and Spanish I retired from full time teaching and began thinking about my next career. I had been a tour guide in Boston one summer way back and thought it would be a great way to use my skills. So in 2008 I began my job as a Sales Rep where I can have a “classroom “ of international guests to talk to every day!

When I am not working, I am very involved with my family and friends. My husband Bill and I have two children, Katrina and Will, now in their 20’s and our very special grandson Austin who is six and king of Legos. Of course Rosie the cat and Molly, our new dog, play an important part in our family. We all love to travel, ski, skate, swim and sometimes play golf or tennis. For me reading and my yoga classes give the necessary downtime. My goals for the near future are to continue to learn Italian, travel more and spend lots of time with family and friends.

What is your favorite vacation spot?
Brewster on Cape Cod, it has beautiful sunsets, beaches, ponds and biking trails.

Which talent would you most like to have?
I love singing, so I would like to have a great voice.

If there was one place you would like to live besides your current city, where would it be?
Paris, because it is a great walking city with lots to do.

What do you most value in your friends?
Loyalty, flexibility, good listening skills and of course a sense of humor.

Who are your favorite writers?
Southern writers like Pat Conroy or Irish writers likeMaeve Binchy. I will try any book!

Meet David Mahl

October 20th, 2014
David Mahl

David Mahl

I was born in the heartland of Des Moines, Iowa, but then moved to the hot deserts of Arizona – and I deplore the heat. I went on a high school vacation to San Diego and I fell in love. After graduation I decided to move to San Diego to enjoy the sun and beautiful beaches. I love being outdoors, working in the garden, and being in nature. That’s probably why my hobbies include planting gardens and restoring things that people have thrown away. You know what they say, “One man’s trash is another man’s treasure”.

I’ve always been connected to Old Town State Park in one way or another. I remember always seeing one particular conductor smiling and ringing the bell as he drove by (Harold Dozier our current Head Conductor) and thought it might be fun working there. One day I saw an ad that they were hiring so I applied. Fifteen years later I’m still here selling tickets and delighting guests in San Diego’s beautiful sunshine.

If you could choose one reality TV show to be on what would it be?
The Amazing Race because I love the chase and the possibility of winning.

Which talent would you most like to have?
I would love to be a talented chef.

Who is your favorite hero of fiction?
Batman for his strength and darkness.

What is your most treasured possession?
My gift of imagination and creativity. “Creative people have the spirit of hope and the gift of striving.”

What is your favorite vacation spot?
Anywhere in the Pacific Northwest where it rains. I love the rain.

Meet Josh Thurston

October 15th, 2014
Josh Thurston

Josh Thurston




Josh is originally from Mechanicsville, VA. After attending Embry-Riddle Aeronautical University in Dayton Beach, he set out on an airline career, working for Spirit Airlines, Air France, and Delta. Following September 11th, Josh began working for Norfolk Southern Railway in various capacities before finding his way to Key West. Today Josh serves as a conductor for Old Town Trolley Tours of Key West.
In his spare time, Josh is an avid bagpiper He has had the opportunity to compete in some of the the best bands on the east coast. Together with his wife, Heidi, and their boxer, they enjoy calling the Keys home.

What do you consider your greatest achievement?
Winning the John Harris Scholarship. This award allowed me to attend the week-long piping school that was put on by the National Piping Center in Glasgow, Scotland. There, I received instruction from some of the best pipers in the world.

What is your most treasured possession?
Henderson Bagpipes!

Who is your favorite hero of fiction?
Severus Snape