Meet the Conductors

Bill is a Red Train veteran and has been with the company since the ’90s.  He relocated to St. Augustine from Chicago, Illinois and appreciates the St. Augustine weather and its rich history. He has a particular interest in the Flagler years and all that he contributed to our city’s history.

I am a Florida native from Jacksonville. After retiring from CSX Railroad, I thought that I would like to drive the Red Trains. I enjoy meeting people and telling them about our history. When you take my tour, you instantly realize I have a deep southern accent-or so I’ve been told. Come and see me here on the Ripley’s Red Trains! All Aboard!

Bruce is a California boy who moved to St. Augustine, drawn in by the history and ambiance. There is nothing about the city that doesn’t intrigue him and he loves inviting guests to our city to show it off. Bruce is one of our many shuttle drivers so when you call for a hotel pick up; you may have the pleasure of meeting him!

Charlie is an original Florida boy who has worked his way up the ranks here. In addition to dispatching and driving, Chuck doubles as our co-manager of the Ghost Train Adventure. He says that there is nothing that could keep him away from the beautiful city of St. Augustine as he just loves the history, art, food and of course, ghosts. He relishes being able to share his stories with his guests, especially the darker side of the city on the night time ghost tours.

Jamie Harris came to us all the way from Australia! It was his mom, and the love of the ocean are what brought him to St. Augustine.  Jamie adores the people that he gets to meet from all over the world and sharing his stories with them.  His favorite part of the city is the beautiful churches that can be found in downtown St. Augustine.

Robin was born and raised in Connecticut and has lived in St. Augustine for nearly 20 years now.  She shares her expertise with our drivers as an ace dispatcher.  She initially came to visit a friend who lived here, and she fell in love with the city and never left. Most recently, she has become a snowbird heading back to Connecticut in the warmer months and dispatching here when the weather is a little too cold up north.  She too enjoys all of the people she gets to meet while working for the trains.

Terry has a unique tie in with Ripley’s as he comes from Alton, Illinois, the home of Robert Wadlowe, the world’s tallest man. He relocated to St. Augustine to be close to his children in his retirement. He takes great pride in showing off our city to his guests and his dry sense of humor is a favorite among riders. He has a unique way of telling the history of our city and loves the Spanish influence dating all the way back to Columbus.

Meet Tim Daly! Tim joined our team in 2019 and came all the way from Yorkshire and West Cork, Ireland!  His accent is a fan favorite among guests.  Tim came to St. Augustine to start a new chapter in his life in the United States.  Having been a tour driver in Ireland, this was a perfect fit. Tim thoroughly enjoys meeting people and sharing his joy for his new home. His favorite part of the city’s history is the golden age.

Meet “Saratoga Ray!”  Ray comes to us from Saratoga Springs, NY where he also acts as a tour guide for the city and the horse racing history of the city when he isn’t in St. Augustine.  He relocated to St. Augustine for the history and his love of all things historic.  He loves interacting with the people who visit here and as a big history buff, he loves sharing its unique history.  His favorite part of the history is Flagler and how he went on to develop so much in Florida.  He also enjoys the history of the man himself, his life, his loves and how he went on to do so much for Florida and especially St. Augustine.

Wayne joins us from Wellington, Colorado. After serving in the US military and being stationed at NAS Jacksonville, he fell in love with the First Coast and in particular, St. Augustine. When Wayne relocated, we got the call from him, and he said that it was his dream to drive a Red Train and share his love of the city. His enthusiasm for the area is evident in his tour.

You may have read about “Smokey” and his “Smokey extras” if you’ve been on Trip Advisor. Smokey relocated his family here in 2005 and hasn’t looked back. He moved here for the outstanding school system and enjoys visiting theaters with his family in the First Coast area. When asked about his favorite part of the job, his answer is “Everything!” He loves being outdoors and having the ability to meet people from all over the world while sharing his amazing knowledge of our city.

Susan was born and raised in New Jersey and now calls St. Augustine home. During the week, she transports children for the St. John’s County schools and she drives shuttles for us when school is out. The beautiful ambiance of St. Augustine led her to call this area home, and she loves the people that she meets on the shuttles.

Bob is our other Ft. Lauderdale native who has “Kind of” retired to St. Augustine.  He initially relocated to St. Augustine for his previous employment with St. Augustine’s General Hospital.  He loves talking about the Flagler era and sharing the amazing growth that he brought to the city.

Daphne was led to St. Augustine to teach yoga and lead ecotours. If you have ever taken her tour, you won’t soon forget it. He enthusiasm and humor are evident in the energy of her tour. She is fascinated with history and especially the natural beauty. She is an expert on how the wading birds in St Augustine led to the passing of the migratory bird act and the founding of the Audubon Society. If you like her tour, you may be lucky enough to catch her on one of our ghost tours too.

Jeff is an upstate New Yorker hailing from Rochester, NY. Jeff is a Coast Guard retiree who relocated and built here in St John’s County. He is a history buff who loves sharing history.  The fort is his favorite landmark in the city.

Hugh Hegarty is a big fan of the “Birds” after relocating from Parkesburg, PA. He enjoys the trains so much that he is our new Red Train manager! Bringing several years of management experience and a few years as a driver, Hugh has jumped right. One of his favorite facts about the city is a little known one. He was amazed to learn that Pedro Menendez brought a master brewer with him on his visit!

Gil is a “Jack of all trades” here at the trains. After relocating here from Bridgeport, CT, Gil drives, he shuttles, he fixes, he builds and a myriad of other tasks here. His favorite thing here is the Hidalgo House because he claims it as his namesake!

Ben Bates is our first and only driver from Johannesburg, South Africa! His story is similar to many others as it was a wonderful lady who led him to St. Augustine.  His accent is a favorite among guests as he enjoys showing off the fort and the rest of the amazing city to his guests.

James is our world traveler who comes originally from Sarasota, FL, and Chicago, IL. You can tell by his photo that he has a colorful personality only matched by his adventurous life. James has toured the world in the music industry and also spent several years working for the circus. His showmanship comes through in every tour and there is never a dull moment on his train! His favorite era is the Gilded Flagler era but he is also fascinated with the Native American pas of our city.