Chad Gallivanter

Cedar Key, Florida has always known how to take a hit.  But between August 2023 and September 2024, this small Gulf Coast island of roughly 700 people absorbed three hurricanes in thirteen months, and a Dock Street fire that tore through the heart of the town's waterfront economy one week before Hurricane Helene made landfall as a Category 4.  This episode traces the sequence: Idalia, Debby,...

Winter Park calls itself the City of Culture and Heritage. This year, it's losing pieces of that heritage faster than it can decide what to do about it.  Tuni's, a 40-year fixture on Park Avenue, was given 30 days to vacate after new landlord Benderson Development declined to renew its lease in favor of a national tenant. The shop isn't closing, it's searching for a new home in...

Historic downtown Winter Garden is one of Central Florida's most admired small-town districts. National Register status. A farmers market drawing thousands every week. Brick storefronts, the West Orange Trail, a boutique hotel built in 1927. A downtown that took decades to build into something people genuinely wanted to be part of.  'And now, in the span of a few months, something is shi...

This summer, America turns 250 - and every city in the country has a story to tell. But St. Augustine's version is different.  When the thirteen colonies signed the Declaration of Independence in 1776, Florida wasn't one of them.  St. Augustine was British East Florida: a Loyalist city, a Loyalist fort, a Loyalist story. And that tension is exactly what makes it worth visiting right now....

Chad returns to Dollywood with a season pass and a specific mission: NightFlight Expedition, the largest single attraction investment in the park's history, opening later this season.  But walking through a park you've known since childhood means seeing more than what's there now.  The Harvey water clock still runs behind the Back Porch Theater, marking time in what used to be the f...

The Flagler Beach Pier is gone - and for a lot of people driving past on A1A, that's a reason not to stop.  This episode asks whether that assumption is right.  Hurricane Ian knocked out the old wooden structure in 2022. What's going up in its place is taller, wider, and built entirely from concrete.  But while those pilings go in, the town is still operating - the Saturday farmers marke...

St. Augustine, Florida has been nominated by USA Today's 10Best Readers' Choice Awards for Most Walkable City to Visit in the United States - and this episode makes the case for why it should win. Voting is open now through June 15, 2026, and you can cast one vote per day at the link below. This isn't just a campaign plug. St. Augustine has a walkability argument that no other city...

Pigeon Forge, Tennessee has no shortage of ways to take your money. But The Island does something different.  It doesn't charge you to walk in. Parking is free. You can spend an entire evening there without ever making one clear decision to spend anything at all.  And yet somehow, people do.  A FloridaRentals.com analysis of TripAdvisor reviews ranked The Island sixth on a list of the biggest...

Plant City sits between Tampa and Orlando, and most people treat it like a pass-through. In this episode, we slow down and take a closer look at what’s actually here. We start inside the original 1909 depot, now the Robert W. Willaford Railroad Museum, where the town’s entire reason for existing comes into focus. From there, it’s a walk through a downtown that still operates the way it was built t...

Just south of Gainesville, Micanopy looks like a place you pass through. A few antique shops. A quiet main street. Live oaks stretching over the road. And then you keep driving. But that misses the point entirely. In this episode, we take a closer look at how this small inland town came to exist in the first place. The story begins long before storefronts and cafés, with a landscape shaped by Payn...

Lakeland isn’t just what you saw in Part One.  There’s a second layer to this city that doesn’t sit out in the open, the places you don’t pass by on accident, the ones you have to know are there.  In this episode, we head deeper into Lakeland to find the spots that give the city its staying power.  That starts at the historic Silver Moon Drive-In Theatre, one of the last operating drive-ins in Flo...

Lakeland, Florida is easy to overlook if you only see it from Interstate 4. Most people pass the exits on their way to Tampa or Orlando and assume they already know the place.  But once you slow down and spend time here, a very different picture starts to emerge.  In this episode of The Gallivanter Podcast, Chad explores ten clues that reveal why Lakeland might quietly be one of the most interesti...

Most people visit Sanford, Florida the same way.  They stroll along First Street, enjoy a drink or dinner downtown, and walk the Riverwalk beside Lake Monroe. It’s an easy place to spend an afternoon, and one of the most charming historic districts in Central Florida.  But Sanford’s story runs much deeper than most visitors realize.  Long before Orlando became the center of the region, Sanford was...

Ocala was horse country long before anyone had heard of the World Equestrian Center.  For decades, Marion County built its reputation quietly. Thoroughbred farms spread across rolling pastureland. Trainers, breeders, and veterinarians developed a network that made this part of Florida one of the most important centers for horse breeding in the United States.  The landscape itself played a role, wi...

Before Ocala was known for horses, farms, or quiet historic streets, one place had already put this part of Florida on the map.  Silver Springs was one of the earliest tourist attractions in the United States.  Long before theme parks defined Central Florida tourism, visitors traveled here to see water so clear that fish, turtles, and submerged trees appeared suspended in midair.  The invention of...

Ocala is often described in simple terms.  Horse country. A gateway to the springs. A place travelers pass through on the way to somewhere else.  But spend a little time here and the picture becomes more complicated.  In this episode of the Gallivanter Podcast, Chad takes a closer look at the city itself.  The walk begins around the historic square in downtown Ocala, where the courthouse anchors a...

One afternoon in March of 1963, a crowd gathered on St. George Street in St. Augustine and looked up toward a balcony.  Standing there was the Vice President of the United States. Not a president yet. Not the architect of the Civil Rights Act. Just Lyndon B. Johnson, visiting America’s oldest city for what seemed, on the surface, like a ceremonial stop.  Johnson had come to dedicate the restored A...

In 1904 a woman arrived in Daytona Beach with almost nothing. Just $1.50… faith… and an idea. That woman was Mary McLeod Bethune , and what she built would become one of the most important historically Black universities in the United States. But the story is even bigger than that. Bethune advised presidents. She organized one of the most influential networks of Black women in American history. An...

Ormond Beach has a habit of hiding its story in plain sight.  Most visitors know it as a quiet coastal town just north of Daytona Beach. A stretch of sand. A scenic drive along the Halifax River. A place where the crowds thin out and the pace slows down.  But long before beach condos and vacation rentals, this shoreline played a very different role in American history.  At the beginning of the twe...

At the northern tip of Amelia Island, where the St. Marys River meets the Atlantic, a massive brick fortress still stands watch.  In this third installment of the Amelia Island series, we step inside Fort Clinch State Park and trace the layered history of Fort Clinch, a 19th-century Third System fort built to guard one of the most strategic harbors in the Southeast.  Construction began in 1847, bu...

Amelia Island is often marketed as a quiet escape on Florida’s northeast coast. But what is it actually like right now?  In this final episode of our Amelia Island series, we step into the present.  From Centre Street in downtown Fernandina Beach to the waterfront, historic neighborhoods, beaches, and state parks, this is a grounded look at what visitors will encounter in 2026.  We revisit the gri...

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...

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 f...

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...

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,...