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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Winter Park looks quiet on the surface, but beneath the brick streets and lakeside parks is one of Florida’s most influential cultural cities. This episode takes you beyond the café patios of Park Avenue and into the deeper story of how a small, carefully planned community became a powerhouse of art, architecture, and historic preservation.

We explore the city’s origins in the 1880s, the citrus empire that vanished overnight, and the reinvention that followed. You’ll hear how Rollins College shaped national conversations, why a world-class Tiffany collection ended up in a small Southern town, and how Hannibal Square changed the political history of Florida in ways most visitors never learn.

Think of this as a guided walk through a place that hides more truth than its postcard image suggests. Winter Park is elegant, thoughtful, and far more important to Florida’s identity than most people realize. By the end, you’ll understand why this small city has shaped taste, culture, and conversation for more than a century.

Wherever you go, you can take the story with you.

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Pigeon Forge is a place most people think they already understand - a blur of neon, traffic, mini golf, dinner shows, and roadside souvenir shops. But beneath all of that? There’s a different story taking shape, one that’s quieter, older, and easier to miss.

In this episode, Chad returns to Pigeon Forge for the first time in a couple of years and takes on a simple question with a complicated answer: What happened to this town?

Over the course of one rainy day, he traces the layers that still define the city’s original character. There’s a stop at the Apple Barn for a familiar morning ritual, a walk through the lesser-traveled side of the Old Mill District, a rediscovery of the steampunk curiosity shop A Long Story Short, a visit with the feline oddities at the Smoky Mountain Cat House, and a zen-like pause inside Micro Garden Plants & More.

Along the way, he reconnects with a few of the places that shaped early Smoky Mountain tourism - including Pigeon River Pottery, where the craft tradition still continues, and Blowing Cave Mill, a lovingly restored 1870s landmark tucked beneath English Mountain.

This isn’t a guide to Pigeon Forge.
It’s a portrait - of the past that lingers, the present that overwhelms, and the small pockets of meaning that still make this town worth revisiting.

New episodes of The Gallivanter Podcast drop regularly.
Listen on Apple Podcasts, Spotify, or iHeart Radio.

For show notes, maps, and additional stories from this trip, visit ChadGallivanter.com.

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When the 2025 government shutdown reached Florida’s Space Coast, it quietly reshaped one of the state’s busiest refuges.

In this episode, Chad Gallivanter visits Merritt Island National Wildlife Refuge, home to spoonbills, manatees, and the shadow of Kennedy Space Center, to document what “open but unstaffed” really looks like. The visitor center is locked behind a chain-link fence. The boardwalk is off limits. The restrooms are closed. A single orange portable toilet stands in for federal infrastructure.

From the rough, rutted loop of Black Point Wildlife Drive to the weathered steps of the observation platform, this is an on-the-ground look at what happens when government stops showing up.

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Florida doesn’t do winter the way the rest of the country does. It invents its own version. From mangrove lagoons lit by kayaks to entire cities wrapped in white light, the Sunshine State turns December into a story of illumination.

On this episode, Chad takes you across a number of unforgettable holiday experiences - the real ones, not the overhyped ones - that show how Florida celebrates without ever pretending to be somewhere else. You’ll walk the centuries-old streets of St. Augustine during Nights of Lights and wander under silk dragons at the Asian Lantern Festival in Sanford.

From Edison’s winter estate in Fort Myers to the wild chaos of Key West’s Lighted Boat Parade, each stop reveals a different side of the season - historic, cultural, and occasionally a little eccentric.

If you think you already know what a Florida holiday looks like, think again.
This is the state seen through light - its traditions, its contradictions, and its magic.

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Dunedin didn’t build itself around a beach; it built around a street. Main Street. That’s the spine - walkable blocks lined with cafés, boutiques, and bookstores, anchored by the Artisan District and the Pinellas Trail that runs straight through town. 

And every spring, TD Ballpark, home of the Toronto Blue Jays, turns baseball into a community celebration that spills well beyond the outfield. 

This episode is a guide to what you’ll actually do here: start at the Dunedin History Museum, wander through the shops and murals, catch a game, and end your day at the Grant Street Inn, a quiet stay just steps from Main Street. 

Not a beach checklist. A clear, thoughtful look at a Florida town that chose Main Street over mayhem - and made it work.

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If you’ve ever wondered how to experience St. Augustine in just one day - and actually do it well - this episode lays out the strategy. 

Not the tourist version. The smart one. 

We’ll start early, before the trolley crowds and tour buses arrive, tracing a path from the Castillo’s first light to the quiet corners of Uptown and West King. Along the way, we’ll talk about timing - when to see the fort, where to park without overpaying, and how to avoid the St. George Street bottleneck without missing what makes it special. 

This isn’t a checklist. It’s a plan, rooted in history, shaped by rhythm, and told from the ground up. 

From the hum of the city gates to the calm at Mission Nombre de Dios, we’ll show how one well-planned day in St. Augustine can feel like a week’s worth of discovery.

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Just west of Orlando, there’s a pair of towns that quietly rewrote the script on what small-town Florida could be. Winter Garden and Oakland - two neighboring communities bound by a bike trail and a shared sense of purpose - have managed to preserve their charm while welcoming the future. In this episode, we explore how Winter Garden’s brick-lined downtown became one of the most walkable destinations in Central Florida, and why Oakland chose a slower, more deliberate path, one rooted in nature and history.

Along the way, we’ll visit local favorites like Ruby & Rust, Adjectives, and the Edgewater Hotel; we’ll stop for coffee at Prairie House, wander Newton Park on Lake Apopka, and discover how the West Orange Trail became the backbone of both towns’ revival.

This is a story about planning, pride, and the kind of community that doesn’t just happen - it’s built, protected, and loved. Whether you’ve been here a dozen times or never at all, you’ll come away seeing these two small towns in a whole new way.

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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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📬 Questions, ideas, or media requests? Email me at [email protected]