Our Concierges on Wheels – Jolley Trolley

Our Concierges on Wheels

Our professional drivers are friendly, accommodating and knowledgeable about each of the cities along the coast; Clearwater Beach, Downtown Clearwater, Dunedin, Palm Harbor, and Tarpon Springs. Each of our drivers have certified qualifications and can easily get you acquainted with the area on your first Jolley Trolley ride. So, all aboard!


Barbara has been living in Clearwater since she moved here when she was very young. With 35 years of experience in professional driving, she affirms that everyone at Jolley Trolley works as a team to provide safe transportation with quality customer service. Her favorite thing about driving our trolleys is being surrounded by passengers. She enjoys conversing with new friends while cruising through the beautiful scenery on our routes.


Brent has lived all over the U.S. and Germany being raised in a military family and has been driving the trolley since 2011. While driving he enjoys observing people having a good time on Clearwater Beach. Living in the area for a long time he still loves seeing dolphins in the bay, and watching the sunsets. You might hear some music on his trolleys and will offer some great info for the Clearwater area.


Home of the Apollo Command Module, CA is where Cary is from and has been driving the Jolley Trolley since 2014. While driving his routes he likes interesting people and especially when some groups break out in a song! He wants his passengers to feel safe and he does his best getting them to where they are going! Ask Cary about current events, restaurants or the sponge docks!


Deveriell has been a part of our Jolley Trolley family since 2018. He is originally from the island of Jamaica and he moved here for his family. Since his immigration to the U.S., he has been a public transportation driver for four years. His favorite Jolley Trolley route is our coastal route. Of all the small towns he drives through on the coastal route, he likes Palm Harbor the most. He encourages his passengers to buy day passes so that they can hop on and off the trolley in each town to see for themselves what each town offers.


Diane, also known as “Bambi” by her Jolley Trolley family, is originally from Wheaton, Maryland. She relocated to the Clearwater area because she wanted year-round warm weather. Diane has been a part of our Jolley Trolley family since 2010 and she has been a transportation driver for 20 years! Tarpon Springs is her favorite trolley stop because of the amazing Greek food and culture. She loves meeting new people and making new friends while driving the trolleys. She says our drivers are always very patient and helpful whether your lost or just looking for something to do.


Dianne is from Mobile, Alabama and has been driving the Jolley Trolley since 2013. While shes driving her routes she enjoys meeting different people from many different places. Listening to her passengers share their experiences makes her day! Dianne offers great advice on places to dine and shop.


Donna has been a part of our Jolley Trolley family since 2016. She enjoys driving the Clearwater Marine Aquarium route and likes to make the trolley experience as enjoyable as the Aquarium and Dolphin Tale Adventure. Donna knows that her passengers like the open trolleys and will share any little bit of history to make their experiences more interesting.


Jackie is from Cincinnati Ohio and has been driving the Jolley Trolley since 2013. She enjoys driving the trolleys and helping people get to where they need to go. Her passengers will receive a positive, informative, happy attitude from her and Jackie will offer awesome places to eat, shop, and find entertainment. She will also recommend places that they can go using their Jolley Trolley/PSTA passes.


Kathleen has been a part of our Jolley Trolley family since 2016. She is originally from Salt Lake City, Utah. While driving the trolley, she enjoys, "Meeting the nicest people from all over the world - they love our beautiful beaches and Jolley Trolley's friendly and knowledgeable drivers. It's the best way to see the sights."


Rich has been a part of our Jolley Trolley family since 2016. He is from Mays Landing New Jersey and joined us this past year. He likes having the front drivers seat while he meets people from all over the world. He says 'being on the trolley does not feel like you are on a bus or shuttle, and you feel like this is a part of your vacation experience.' Rich will let you know the best way to get to places and the best places TO GO!


Robert has been a part of our Jolley Trolley family since 2016. He is from Carmel Indiana. He enjoys learning about his passengers from many parts of the world and their different cultures. He says "We get to share a small piece of our lives in the brief time we have together." The passengers get to sit back and relax while enjoying the fantastic scenery Florida has to offer. Robert might get to know you quickly and will suggest some entertainment or restaurants to your liking.


Yvonne is from Detroit MI and has been with us since 2013. She enjoys driving passengers and getting them safely to their destinations. Yvonne says that her passengers like the sites and all the different places to go. She will recommend some great restaurants, shops, and beaches if you ask her to share!


Troy is originally from New Jersey and decided to move the area because he wanted a change in scenery. His favorite part of the coastal route is Tarpon Springs because it's beautiful and unique. He likes driving the coastal route because of the people that he meets and thinks it's the most enjoyable transportation service in the area because of the quality of the staff.


Jean has been a transportation service driver for 30 years and is originally from New Jersey. She moved to the area for the warmth and the sunshine. Her favorite areas along the coastal route are Dunedin and Tarpon Springs. Jean enjoys driving a Jolley Trolley because of the nice passengers she meets. 


Lorraine is mainly from the West coast and has lived in California, Las Vegas, and Texas. She gradually made her way to Florida 35 years ago for the beautiful beaches, warm weather, and to be near her mom. She enjoys driving the Dunedin route, especially down Edgewater because of the water view. She also enjoys Main Street because it's pet friendly, family-oriented, and has so many things to do. She likes driving for Jolley Trolley because it's a small organization and she knows everyone cares about one another.


Sebrina is originally from St. Petersburg and was born and raised in the area. Her favorite part of the route is Dunedin because it's quiet, beautiful and family-oriented. She likes driving the trolley because of the people that she works with and she enjoys meeting most of the passengers that she drives. She feels a Jolley Trolley is special transportation because she can help passengers at stops that are convenient for them and it makes them feel special.


Colleen recently started driving for Jolley Trolley and is originally from upstate New York. She decided to move to the area to be closer to her family. She loves driving the coastal route and taking riders to the microbreweries in the area. She enjoys driving a Jolley Trolley because of the beautiful scenery and the relaxed atmosphere. She wants riders to know that the Jolley Trolley is the most enjoyable transportation in the area because of the personality of the vintage trolleys themselves.


Josh is originally from Colorado, but moved to Florida to escape the cold weather and to be closer to his family in Tampa. He has over 22 years of professional driving experience and more than 5 years transporting the general public. He says he doesn't have a favorite route because each area is so different and offers something different to each rider. Josh says, "The Jolley Trolley offers some truly special qualities that include a friendly, personable experience that you wouldn't find on other public transportation forums." He also says, "The Jolley Trolley offers a friendly and knowledgeable crew that's interested in the happiness and concern of the riders."


Dave is originally from Minneapolis and moved to Florida to escape the frigid cold winters there. He enjoys driving the Coastal Route to Tarpon Springs because he likes to ask passengers where they ate (Tarpon Springs is famous for traditional Greek fare). He has been in transportation for over 10 years and likes it because he can talk to passengers about their travel experiences. He feels driving the Jolley Trolley is special because of the ambiance and getting to see the reactions of the people taking the trolley for the first time.