Chad Gallivanter

Chad Gallivanter Your guide to the overlooked, the historic, and the fascinating corners of travel. Based in Florida, but chasing stories everywhere.

Each episode unfolds in deliberate, well-structured segments, weaving archival research with on-the-ground travel insight. I'm Chad Gallivanter, a former broadcast journalist and current full-time video producer. If you're looking for informative travel podcasts that won't waste your time, you've come to the right place! My content is created for the smart traveler who values facts and research, i

n addition to intelligent opinion and commentary. This podcast is dedicated to offering tips, tricks and secrets to help you plan your next vacation while providing historic background and context on the places featured. I live in Central Florida with my wife Abby. We’re proud parents to Pinkerton, a tuxedo cat. New podcasts are released every week. I'd love to have you subscribe and hear your feedback in the comments!

09/01/2026

I've lived around DeLand for twenty-five years. It took me half of that to find out one of downtown's most familiar buildings used to be the county jail.

It sits half a block off Main Street, cinderblock and steel bars, staring straight across the intersection at the domed 1929 courthouse that ends up in every postcard of downtown. One side of that corner got grandeur. The other got a chain-link exercise yard and almost forty years of nobody agreeing on what comes next.

Right now the city is stuck choosing between two plans: turn the lot into a public square, or sell it outright. Neither side is in a hurry to pick.

New episode is up now. Town square, or sell it? Tell me where you land in the comments.

If you live in Ivanhoe Village, you've driven past this building a thousand times. It sits right on Orange Avenue. And i...
08/17/2026

If you live in Ivanhoe Village, you've driven past this building a thousand times. It sits right on Orange Avenue. And if you're like most of your neighbors, you have no idea why it's been empty for over a decade.

It's not for lack of trying to fill it. There's a broker. There's been interest. The building survived a power-outage era, a full renovation, and a second life as a stage for the Orlando Ballet. Nothing has closed.

The story starts in 1897, when a local judge built Orlando's first water and power plant right on that same shoreline. In 1923 the newly formed Orlando Utilities Commission rebuilt it, and for 35 years it kept the whole city's lights on. Then a mold scare in 2013 emptied it out for good.

Turns out the reason nobody can close a deal has nothing to do with money or neglect. It's something baked into that exact spot before Orlando ever built there at all, and it's still sitting under the building right now.

New episode, Powerless, is up now. Link in comments.

The sand on Anna Maria Island didn’t start on Anna Maria Island.It started as quartz crystal in the Appalachian Mountain...
07/30/2026

The sand on Anna Maria Island didn’t start on Anna Maria Island.

It started as quartz crystal in the Appalachian Mountains, broke down over millions of years, and rode the rivers all the way to the Gulf coast.

That’s how our new episode opens, and it changes how you look at every beach chair on the island.

From there we move through the island’s fishing village roots, the bridge that changed everything, and the businesses still holding the line against a chain-store future.

One of those businesses is AMI Coconuts.

We sat down with owner Robert McGraw and let him tell the story in his own words, no narrator standing between him and the camera.

We also stopped in Cortez to check on The Fox Mercantile, still carrying the old fishing village forward.

New episode is up now. Link in comments.

There’s a beach in Florida where you’re not allowed to swim. Three-quarters of a mile of coquina rock at Washington Oaks...
07/29/2026

There’s a beach in Florida where you’re not allowed to swim. Three-quarters of a mile of coquina rock at Washington Oaks Gardens, empty most days for that exact reason.

It’s one of nine stops in the new Gallivanter episode, Florida’s Secret Shores, running the length of the Atlantic coast from an 1840s brick fort at the northern tip of Amelia Island down to the last wild stretch of the Keys at Bahia Honda. Little Talbot Island, Anastasia, Gamble Rogers, Sebastian Inlet, Bill Baggs Cape Florida, and a bonus stop at Blowing Rocks Preserve on Jupiter Island.

None of these show up on the postcards. That’s the point.

Listen wherever you get podcasts, or watch on YouTube.

A future king of England vacationed in DeBary, Florida.Not a theme park. Not a marketing line. In 1871, a wine importer ...
07/28/2026

A future king of England vacationed in DeBary, Florida.

Not a theme park. Not a marketing line. In 1871, a wine importer named Frederick deBary built an 8,000-square-foot hunting estate on the St. Johns River, and the official record says his guest list included the Prince of Wales, the man who later became King Edward VII, along with two sitting U.S. presidents and names like Astor, Gould, and Vanderbilt.

This was decades before Henry Flagler ever built a hotel or sold Florida as a place anyone could visit. Back then, a winter in Florida wasn’t something you bought. It was something you were invited to. DeBary Hall is the building that’s still standing to prove it.

New episode: DeBary Hall, and why a future king stayed here.

Link in comments.

Winter Park calls itself "The City of Culture and Heritage."But this year, one of its most iconic lakefront estates is s...
06/24/2026

Winter Park calls itself "The City of Culture and Heritage."
But this year, one of its most iconic lakefront estates is sitting under an active demolition permit. An 80-year-old hardware store just closed its doors for good. And a boutique that's been on Park Avenue for 40 years got 30 days to vacate.

None of this is illegal. That's the point.

Winter Park didn't get a historic preservation ordinance until 2001 - decades behind most comparable Florida cities. And the one it has? It requires a two-thirds vote among property owners to even form a historic district. That's the highest bar in the state.

So when developers buy a Park Avenue block and a family decides not to list their estate on the historic register, the city can't stop what happens next. It was designed that way.

If you've ever walked down Park Avenue and assumed someone was protecting what makes it worth walking, this one's for you.

Episode out now.

Historic downtown Winter Garden is one of the best small-town main streets in Central Florida. National Register of Hist...
06/18/2026

Historic downtown Winter Garden is one of the best small-town main streets in Central Florida. National Register of Historic Places. A farmers market that draws thousands every week. The West Orange Trail. Brick storefronts that took decades to build into something worth showing up for.

And then, in the span of a few months, the for-lease signs started appearing.

Three Birds Café. Writer’s Block Bookstore. Driftwood Market. Polka Dotz. Ruby and Rust. Business after business announcing closings or relocations - and the explanations kept pointing in the same direction. Lease nonrenewals. Ownership changes. Rents that no longer made sense for the people who built the place.

One entity has acquired more than 36 properties along Plant Street since 2015. Over $40 million spent. A February city commission meeting packed with residents demanding answers that nobody was legally required to give.

This is not a story about one café closing. This is a story about what happens when a historic downtown gets successful enough to price out the businesses that made it worth visiting in the first place.

New podcast episode in the comments.

You did not go to The Island in Pigeon Forge for the dinosaurs.But there they are, scattered along the walking paths, an...
05/29/2026

You did not go to The Island in Pigeon Forge for the dinosaurs.

But there they are, scattered along the walking paths, and you watch a family stop in front of one. A kid points toward the next. A group that was about to leave slows down and drifts deeper into the property instead.

That’s the whole game. The dinosaurs aren’t central to the Smokies. They aren’t even the main attraction at The Island. They’re placed exactly where they need to be to stop you, turn a pause into a photo, and turn a photo into another hour.

In this episode I get into why The Island is one of the best-built tourist traps in Pigeon Forge, how the land used to be Porpoise Island back in the early ’80s, and why the real trap might be the entire Parkway.

Episode out now.

St. Augustine was built for walking in 1565. The streets were designed for human feet because that was the only way peop...
05/28/2026

St. Augustine was built for walking in 1565. The streets were designed for human feet because that was the only way people moved. Four hundred and sixty years later, those same streets are in the running for USA Today’s Most Walkable City to Visit in America.

And they should win.

We put together a full episode on this one. Not just the campaign and how to vote, but the streets and neighborhoods that make the argument undeniable. The ones every visitor finds, and the ones most of them walk right past.

Lincolnville. Aviles Street. The bayfront seawall. The Uptown corridor along San Marco. All of it within a walk of each other in a city that has been doing this longer than the country has existed.

Voting is open now through June 15th. One vote per day. Link to vote and to the full episode in the first comment.

04/29/2026

The Great Food Truck Race from Food Network was at Dollywood today and so were we!

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