Chad Gallivanter

Chad Gallivanter
  • 5.0 (2)
  • Places & Travel

Chad Gallivanter is your guide to the overlooked, the historic, and the just-plain-fascinating corners of travel. Based in Florida but chasing stories everywhere, Chad blends investigative curiosity with a storyteller’s pacing - digging deep into local history, cultural quirks, and the moments that shape a place’s identity. Each episode unfolds in deliberate, well-structured segments, weaving archival research with on-the-ground travel insight. Sometimes it’s a deep dive into a city’s forgotten past. Other times, it’s a smart, sensory-rich exploration of where to go now. Always fact-checked, always engaging, and always told like a story you can’t stop listening to.

  1. May 28

    The Most Walkable City in America Might Be in Florida. Here's the Proof.

    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 on this list can make: its streets were designed for human foot traffic in 1565, more than 200 years before the United States existed. The city's compact historic core - laid out according to Spanish colonial planning principles that prioritized pedestrian movement - puts the Castillo de San Marcos, the Cathedral Basilica, Flagler College, the Plaza de la Constitución, and dozens of restaurants and galleries within a few blocks of each other. That's not modern urban planning. That's 460 years of infrastructure that was never designed around a car. In this episode we break down what the USA Today campaign actually is and how voting works, why St. Augustine's case for walkability is fundamentally different from every other city on the list, and where to actually walk when you're there - including the corridors most visitors never find. We cover St. George Street and the historic downtown, Aviles Street (the oldest documented street in the United States), the Matanzas bayfront seawall, the Lincolnville Historic District and its Civil Rights history, the Uptown district along San Marco Avenue, and King Street's concentration of Gilded Age architecture. St. Augustine has landed as high as 4th on this list in previous years. This year it should be number one. Go vote. 🌎 Keep Gallivanting With Me If you liked this story, you’ll love what’s waiting on my YouTube channel: youtube.com/@ChadGallivanter See more photos, behind-the-scenes, and upcoming trips on Instagram: instagram.com/ChadGallivanter More travel stories, history deep-dives, and extras live at: ChadGallivanter.com 📬 Questions, ideas, or media requests? Email me at info@ChadGallivanter.com

    12 min

  2. May 28

    Flagler Beach Without the Pier: Is It Still Worth the Stop?

    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 market, the Gallery of Local Art, Swillerbees, the Compass Hotel by Margaritaville.  Locals are still showing up. Visitors are still finding reasons to pull over.  We talk to the people who are here now, watching the build and choosing to stay.  This is Flagler Beach before the pier comes back. And the question is whether the town is worth showing up for before it does. 🌎 Keep Gallivanting With Me If you liked this story, you’ll love what’s waiting on my YouTube channel: youtube.com/@ChadGallivanter See more photos, behind-the-scenes, and upcoming trips on Instagram: instagram.com/ChadGallivanter More travel stories, history deep-dives, and extras live at: ChadGallivanter.com 📬 Questions, ideas, or media requests? Email me at info@ChadGallivanter.com

    9 min

  3. May 14

    The Island in Pigeon Forge: No Admission. No Escape

    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 tourist traps in the United States.  One reviewer called it a "Good Tourist Trap." Another said they "ended up spending way more time here than expected."  That raises a specific question. Not whether The Island is popular - it clearly is. Not whether it is clean or well designed - it clearly is both.  The real question is whether a place can be a tourist trap without disappointing you. Whether the whole thing can be enjoyable, well built, and still fundamentally designed to hold your attention longer than you planned.  This episode makes the case that it can. And that the dinosaurs prove it. 🌎 Keep Gallivanting With Me If you liked this story, you’ll love what’s waiting on my YouTube channel: youtube.com/@ChadGallivanter See more photos, behind-the-scenes, and upcoming trips on Instagram: instagram.com/ChadGallivanter More travel stories, history deep-dives, and extras live at: ChadGallivanter.com 📬 Questions, ideas, or media requests? Email me at info@ChadGallivanter.com

    17 min

  4. May 7

    You’re Skipping Plant City. That’s a Mistake.

    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 to, including a stop inside State Theatre Antiques, a preserved 1939 movie house now filled with large-scale vintage pieces and still used for live events. Along the way, there are places to sit and stay a while, including Whistle Stop Cafe and Propagation Whiskey Bar and Kitchen, along with smaller stops like The Kandy Shoppe. Just outside downtown, the agricultural side of the town comes into view at Parkesdale Farm Market, where strawberries move in volume that’s hard to miss. A few minutes beyond that, inside Edward Medard Conservation Park, the terrain changes completely. The area known as Sacred Hills, shaped by former phosphate mining, creates a landscape that doesn’t resemble the rest of Central Florida and rewards anyone willing to climb through it. We wrap up at Keel Farms and take a look at how the Florida Strawberry Festival grew from an agricultural showcase into one of the largest annual events in the region. Plant City doesn’t ask for your attention. But it holds it once you give it. 🌎 Keep Gallivanting With Me If you liked this story, you’ll love what’s waiting on my YouTube channel: youtube.com/@ChadGallivanter See more photos, behind-the-scenes, and upcoming trips on Instagram: instagram.com/ChadGallivanter More travel stories, history deep-dives, and extras live at: ChadGallivanter.com 📬 Questions, ideas, or media requests? Email me at info@ChadGallivanter.com

    12 min

  5. Apr 29

    Don’t Drive By Micanopy, Florida - The Story Behind This Historic Town

    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 Paynes Prairie, a Seminole leader whose name still marks the town, and a federal road that helped determine where people stopped and settled in early Florida. From there, the history deepens. We look at the role of Micanopy during a time when the United States was expanding into the territory, the impact of the Second Seminole War, and how transportation routes like the Bellamy Road shaped the town’s early development. What survives today is not just a preserved streetscape. It’s a place where multiple layers of Florida history are still visible if you know where to look. This episode focuses on how Micanopy came to be, and why it still looks the way it does. 🌎 Keep Gallivanting With Me If you liked this story, you’ll love what’s waiting on my YouTube channel: youtube.com/@ChadGallivanter See more photos, behind-the-scenes, and upcoming trips on Instagram: instagram.com/ChadGallivanter More travel stories, history deep-dives, and extras live at: ChadGallivanter.com 📬 Questions, ideas, or media requests? Email me at info@ChadGallivanter.com

    12 min

  6. Apr 22

    Lakeland, Florida: The Spots Most People Miss

    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 Florida, where double features still run under the night sky and the experience hasn’t been repackaged for modern audiences.  From there, the focus shifts to places that feel completely different from downtown but are just as important to understanding how Lakeland works. At Bonnet Springs Park, a former railyard has been transformed into one of the most thoughtfully designed public spaces in Central Florida, with elevated boardwalks, shaded trails, and wide open areas that are actually usable in the Florida heat. It’s a place locals return to, not just something to check off once.  Then there’s Circle B Bar Reserve, where the city gives way to something much older. This is real Florida landscape, marshes, oak hammocks, and wildlife that doesn’t keep its distance. Alligators, wading birds, and long stretches of trail make this one of the most active wildlife viewing areas in the state, and it’s entirely free to visit.  This isn’t a highlight reel.  It’s a closer look at the parts of Lakeland that don’t advertise themselves, but end up being the reason people come back.  If you watched Part One, this is where the picture fills in.  🌎 Keep Gallivanting With Me If you liked this story, you’ll love what’s waiting on my YouTube channel: youtube.com/@ChadGallivanter See more photos, behind-the-scenes, and upcoming trips on Instagram: instagram.com/ChadGallivanter More travel stories, history deep-dives, and extras live at: ChadGallivanter.com 📬 Questions, ideas, or media requests? Email me at info@ChadGallivanter.com

    9 min

  7. Apr 15

    Lakeland, Florida: 10 Clues This City Is More Interesting Than It Looks

    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 interesting small cities in Central Florida.  The journey begins with the lakes that shaped the city’s layout and the swans that have become one of its most recognizable symbols. From there, the story moves through the largest single-site collection of Frank Lloyd Wright architecture in the world at Florida Southern College, the creative energy of the Dixieland neighborhood, and a downtown built around Lake Mirror that blends historic landmarks with independent shops and cafés.  Along the way you’ll discover places like Born & Bread Bakehouse, Inklings Book Shoppe, Hillcrest Coffee, LoveBird Almost Famous Chicken, Dixieland Relics, Hollis Garden, The Joinery, Scout & Tag, Pressed Books & Coffee, and Mitchell’s Coffee House.  The episode also explores some of Lakeland’s deeper cultural layers, including the Ashley Gibson Barnett Museum of Art and the musical connection behind the restaurant Grievous Angel.  Taken together, these places reveal a city that’s far more interesting than most people expect.  If you’re planning a visit to Central Florida, or simply curious about the places that sit between the bigger destinations, Lakeland may deserve a closer look.  This is the first episode in a two-part Lakeland series. 🌎 Keep Gallivanting With Me If you liked this story, you’ll love what’s waiting on my YouTube channel: youtube.com/@ChadGallivanter See more photos, behind-the-scenes, and upcoming trips on Instagram: instagram.com/ChadGallivanter More travel stories, history deep-dives, and extras live at: ChadGallivanter.com 📬 Questions, ideas, or media requests? Email me at info@ChadGallivanter.com

    13 min

  8. Apr 9

    7 Things Most People Miss About Sanford, Florida

    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 a transportation hub along the St. Johns River. Steamboats once docked along the same shoreline where people gather today for sunsets.  European immigrants arrived to farm the land. A booming celery industry earned the city the nickname “Celery City.”  Fires reshaped the architecture of downtown. And the town itself carries the name of a diplomat who believed this quiet bend in the river could become something much bigger.  In this episode of The Gallivanter Podcast, Chad explores seven things most people miss about Sanford, Florida, the details, stories, and historical moments that explain why the city looks and feels the way it does today.  If you’ve only experienced Sanford as a pleasant waterfront town, this episode reveals the deeper history hiding in plain sight.  🌎 Keep Gallivanting With Me If you liked this story, you’ll love what’s waiting on my YouTube channel: youtube.com/@ChadGallivanter See more photos, behind-the-scenes, and upcoming trips on Instagram: instagram.com/ChadGallivanter More travel stories, history deep-dives, and extras live at: ChadGallivanter.com 📬 Questions, ideas, or media requests? Email me at info@ChadGallivanter.com

    9 min
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Ratings & Reviews

5
out of 5
2 Ratings

About

Chad Gallivanter is your guide to the overlooked, the historic, and the just-plain-fascinating corners of travel. Based in Florida but chasing stories everywhere, Chad blends investigative curiosity with a storyteller’s pacing - digging deep into local history, cultural quirks, and the moments that shape a place’s identity. Each episode unfolds in deliberate, well-structured segments, weaving archival research with on-the-ground travel insight. Sometimes it’s a deep dive into a city’s forgotten past. Other times, it’s a smart, sensory-rich exploration of where to go now. Always fact-checked, always engaging, and always told like a story you can’t stop listening to.

Information

  • Creator
    Chad Gallivanter
  • Years Active
    2025 - 2026
  • Episodes
    40
  • Rating
    Clean
  • Copyright
    © 2026 Chad Gallivanter
  • Show Website
    Chad Gallivanter