While long-time locals may feel like they’ve been there, done that, when it comes to Fernandina Beach and St. Augustine, these two coastal towns whisper centuries of tales to travelers willing to slow down and listen. Move beyond Centre Street, St. George Street, Fort Clinch and the Castillo de San Marcos. Hop aboard a trolley where you’ll learn of legendary locals, mysterious lore and find places to explore off the beaten path.

 Amelia Island

Once home to indigo and cotton plantations, Amelia Island is now known more for its golf courses, main street shops and oceanfront resorts. But fascinating stories of freedom are woven into the communities of Amelia Island and Fernandina Beach.

“Amelia Island is the same size as Manhattan,” Amelia Island Trolley’s tour guide Connie Claxton told us as the trolley rolled past baseball fields and a memorial. “Senator David Yulee laid Fernandina out on a grid like Manhattan Island, including our Central Park. You’ll see the Veterans’ Memorial next and if anyone has served our country, thank you very much for doing so.”

History unfolds as the tour winds past homes with rich stories to tell. “The Williams House is now one of our 10 bed-and-breakfasts but years ago, it had a hidden room to house escaping slaves,” Claxton says. “The family sent a message that it was safe to come by placing candles at certain angles in windows and laying a quilt with a specific pattern on the porch.”

Hurricane Dora, which tore up Florida’s coast in 1964, all but destroyed a comical piece of Fernandina’s history. “Looking out to your right, you’ll see Florida’s oldest continually operated putt putt.” I laugh because this verbiage is very familiar as a resident of St. Augustine. “Dora wiped out all oceanfront businesses including our beachside bowling. The putt putt is all that remains. They had to dig it out from under several feet of sand.”

Amelia Island Trolleys run twice a day and each tour lasts 90 minutes. Filled with introductions to founding fathers such as Senator David Yulee, who moved the entire city of Fernandina from the north end of the island to where it sits today to better accommodate the railroad, and Abraham Lincoln Lewis, Florida’s first African American millionaire who established American Beach, this tour is geared to adults. Although, seeing Pippi Longstocking’s home may prompt you to share a childhood memory with a new generation.

St. Augustine

A ride aboard St. Augustine’s Old Town Trolley is part entertainment, part education and part people mover. With trolleys rolling past 23 stops every 15 minutes, a visit to St. Augustine wouldn’t be the same without the trolley’s clanging bell.

While the basic narrative is the same regardless of the trolley driver, each cast member incorporates their interests, additional research and humor into the tour, making it fun to ride again and again. “If you were to turn right out of this parking lot,” Davey Jones tells us as we wait to cross traffic, “you’d drive past the Florida School for the Deaf and Blind. It’s a beautiful campus and we’ve had some famous students! Ray Charles was here from age 7 to 14. Rumor has it he snuck out and played in Lincolnville clubs on the weekends!”

As the trolley winds through Old Town, St. Augustine’s rich history comes alive. Founded in 1565, St. Augustine is the oldest continually occupied city in the United States. In a country where stories of our founding are centered in New England, it’s fascinating to learn that the first Thanksgiving happened here on the First Coast, 55 years before Jamestown and that St. Augustine was “undergoing urban renewal” when Williamsburg and Jamestown were founded.

After passing the City Gates, which were built in 1808, Davey Jones encourages passengers to disembark at the head of St. George Street. “Walk past 150 years of history here on St. George. You’ll see the oldest wooden schoolhouse, our Colonial Quarter living history museum and plenty of shops to spend your money in!” he quips.

Humor and history are hallmarks of Old Town Trolley, which aims to make the whole experience fun and informative.


Left: Amelia Island Trolley tour guide, Connie Claxton. Right: Long ago, trolleys were a major form of public transportation in Fernandina Beach.


Left: The “Flagler” Memorial Presbyterian Church is on the trolley tour of historic St. Augustine. Right: Davey Jones, tour guide of St. Augustine’s Old Town Trolley .

Amelia Island Trolley z

A view of the lighthouse on Amelia Island from the Amelia Island Trolley.