In this episode of the Gallivanter Podcast, we examine one of the most unusual decisions in Florida town planning.

Fernandina Beach did not simply expand over time. It relocated.

Before Centre Street became the commercial spine visitors recognize today, the original town stood farther north in what is now Old Town Fernandina. Established during the Spanish period, the settlement faced the Amelia River, built for harbor control, trade, and defense. Its layout reflected maritime priorities, not tourism or rail commerce.

By the early nineteenth century, shifting channels, marsh constraints, and the growing importance of rail access forced a choice.

Adapt the original site at great cost, or move.

Fernandina chose to move.

In this episode, we walk through the logic behind that decision, how the new grid was laid out, why Centre Street became central, and how Old Town transitioned into a quiet residential layer of history that still exists today. Understanding this relocation explains why downtown Fernandina feels deliberate, why Old Town feels separate, and how railroads reshaped Amelia Island’s trajectory.

This is Episode Two of our four-part Amelia Island series.

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NOTES FROM AMELIA ISLAND is a four-part narrative series from The Gallivanter Podcast about how places become what they are, not through slogans or branding, but through a long chain of choices, accidents, and absences.

Amelia Island sits just off Florida’s northeast coast, close enough to the state’s major historical currents to have been swept up in them, yet curiously untouched by many of the forces that transformed the rest of Florida into something louder, faster, and more uniform.

This series looks at Amelia Island and Fernandina Beach the way a historian reads a landscape. Not as a postcard, but as a record. Railroads that never arrived. Ports that should have boomed and didn’t. Industries that flared briefly and vanished. Preservation movements that succeeded when others failed. Small decisions that quietly compounded over decades.

Each episode traces a different layer of that story, moving between past and present, and using the modern island as evidence of what happened long before most visitors ever set foot here.

Episode 1: The Island the Railroad Passed By

The first episode begins with a simple observation. Amelia Island never became a railroad hub. Not because it lacked potential. Not because people didn’t try. But because, at several critical moments in the nineteenth and early twentieth centuries, powerful rail interests chose to build elsewhere.

Those decisions redirected capital, labor, and population toward other Florida ports and interior cities, and left Amelia Island on a parallel track. Close to growth, but never at its center.

Episode One examines Fernandina’s early promise as a deep-water port, the competing railroad schemes that surrounded it, Henry Flagler’s expansion strategy along Florida’s east coast, and how being bypassed ultimately preserved a walkable downtown, a human-scaled street grid, and a town that never had to be rebuilt around mass automobile tourism.

Rather than telling the story as nostalgia, this episode treats Amelia Island’s present-day character as a consequence. A product of infrastructure choices, economic pivots, and moments when history quietly turned left instead of right.

Notes From Amelia Island is about learning how to read places differently.

Not for trivia.
Not for bucket lists.
But for understanding why a place behaves the way it does when you arrive.

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St. Augustine has no shortage of breakfast spots. The hard part is knowing which ones are actually worth your time.

In this episode of The Gallivanter Podcast, Chad walks through his go-to breakfast places around St. Augustine, from longtime local institutions to a few quieter favorites that don’t always make the tourist lists. Along the way, you’ll hear practical details about where each spot is located, what they do well, when lines tend to form, and what to order if it’s your first visit.

This is a guide to navigating breakfast in America’s oldest city with a little more confidence and a lot less guesswork.

Perfect for first-time visitors, repeat travelers, and anyone who takes breakfast seriously.

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DeLand doesn’t usually shout for attention.

It doesn’t need to.

In this episode of The Gallivanter Podcast, Chad walks through ten places that quietly define DeLand, Florida. Not a checklist. Not a hype reel. A practical, ground-level look at the streets, parks, shops, and institutions that shape how this town actually operates day to day.

You’ll hear the stories behind longtime landmarks, why certain businesses ended up here in the first place, and how DeLand balances its small-town core with a steady undercurrent of reinvention. From downtown blocks and historic corridors to places most visitors don’t expect to find in Volusia County, this is a local’s guide built around context, history, and firsthand experience.

If you’re planning a visit, considering a move, or just curious how a real Central Florida town holds together, this episode offers a clear, honest starting point.

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Orlando has a working antiques scene that most visitors never see, and that’s exactly where this episode goes.

In this podcast, Chad walks through ten antique stops across the Orlando area, from long-running dealers and multi-vendor rooms to smaller shops tucked into places you wouldn’t expect. These are not tourist curiosities or weekend pop-ups. They’re places with real inventory, real dealers, and very different personalities, depending on what you’re hunting for and how you like to browse.

We move around the city, talk about what each stop actually does well, and share practical context, where they’re located, what kind of pieces tend to show up, and which ones make sense if you’re looking for furniture, architectural salvage, collectibles, or just an interesting room to spend some time in.

If you’ve ever thought Orlando didn’t have much of an antiques scene, or you’ve only scratched the surface, this episode is a useful place to start.

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Mount Dora, Florida is one of those towns that rewards repeat visits. In this episode of The Gallivanter Podcast, I’m sharing how we do Mount Dora, ten places we return to again and again, and why they’ve earned that spot for us.

This isn’t a definitive travel guide or a rushed one-day itinerary. It’s a personal, experience-driven look at the businesses and spots that consistently make a Mount Dora visit better, whether you’re visiting for the first time or coming back for another weekend.

Along the way, we talk about Belgian-style pomme frites at The Salted Fry, antique hunting at Renninger’s, the Modernism Museum’s connection to David Bowie and the Memphis design movement, curated vintage finds, tea stops that make wandering easier, outdoor outfitters that support the lakes and trails around town, relaxed pizza with indoor and outdoor seating, and handcrafted chocolate truffles you can sometimes watch being made.

If you’re planning a Mount Dora weekend, looking for a thoughtful Central Florida day trip, or just want a deeper understanding of why this town keeps pulling people back, this episode is designed to help you enjoy Mount Dora with more intention and less guesswork.

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Step inside Cracker Christmas at Fort Christmas, the annual two day pioneer celebration that transforms a quiet corner of eastern Orange County into one of the most distinctive holiday events in Florida.

This episode takes you beyond the craft tents and demonstrations and into the story behind the event itself, tracing how a reconstructed Second Seminole War fort became the gathering place for a community that protects and teaches its history one demonstration at a time.

We explore where the event began in the late 1970s, why it has grown into the Fort Christmas Historical Society’s largest celebration, and how local clubs like the 4 H, FFA, the Women’s Club, and the Boy Scouts depend on it for essential fundraising.

Along the way, the episode examines the origins of the term “Florida Cracker,” the pioneer skills still demonstrated today, and the surprising traditions of Christmas, Florida, including the annual rush to the post office for that famous seasonal postmark.

Whether you missed this year’s Cracker Christmas or are discovering it for the first time, this deep dive reveals why the event resonates far beyond the festival weekend and why Fort Christmas remains a powerful monument to Florida’s early frontier story. If you enjoy thoughtful travel storytelling with strong historical context, this episode is for you.

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For most visitors, Nights of Lights in St. Augustine is a holiday spectacle, a glowing postcard brought to life. But the real story began long before electric bulbs lined the rooftops. This episode traces the deeper history of how St. Augustine marked the holidays across four and a half centuries, from Spanish colonial celebrations to the quieter rituals that carried into the American era.

Nights of Lights is not the flashiest display, and it was never meant to be. Its power comes from something older, something rooted in the city’s long tradition of using light to mark the season. By the time the modern event emerged in the 1990s, the foundation had already been laid.

In this episode, we look at where those traditions came from, how they evolved, and why Nights of Lights became one of the most enduring holiday experiences in the country. And toward the end, a reflection on why this event creates such a strong pull, a sense that you’ve stepped into a different place and a different century, even if just for an evening.

If you enjoy this episode of The Gallivanter Podcast, make sure to follow or subscribe on Apple Podcasts, Spotify, and iHeart Radio. For more travel stories and detailed show notes, visit ChadGallivanter.com.

Wherever you go, take the story with you.

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If you liked this story, you’ll love what’s waiting on my YouTube channel: youtube.com/@ChadGallivanter
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More travel stories, history deep-dives, and extras live at: ChadGallivanter.com

📬 Questions, ideas, or media requests? Email me at info@ChadGallivanter.com