The premiere of the show's Florida run. Born and raised by the ocean, Brian dives into Clearwater Beach's white sand and carnival energy — and celebrates shedding 55 pounds by hurling himself off a bungee rig. "What's the worst that could happen? A lot!"
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Where the episode goes
Pier 60 is the heart of it: banana boats, parasails, pirate ships, and the nightly sunset festival crowd — including fire dancers working as the sky turns orange. Brian rents a beach buggy for a ride along the shore, then shuffles the main strip past spots like Hooters and Surfside. Pro tip from the episode: skip the car, hop the trolley, and pack hydration, a towel, and a camera.
The food centerpiece is the Bait House, a dockside mom-and-pop spot that's been thriving for over 50 years. Longtime waitress Sherry walks Brian through the menu: drunken shrimp in a savory beef-gravy sauce (his verdict: life-changing), grilled and blackened fish fresh enough to skip the tartar sauce, and local pours like Mango Hefe from House of Beer and a Key Lime Cider. You can even buy bait and tackle and catch your own lunch off the dock.
Then the Gulf steals the show: setting out from the marina aboard the Damn Lucky, Brian's crew gets surrounded by a pod of wild dolphins surfing the wake — left, right, everywhere.
Episode moments
- The bungee jump above the beach — 55 pounds lighter and airborne
- Beach buggy ride along the shore
- Drunken shrimp and dock talk with Sherry at the Bait House
- The wild dolphin pod around the Damn Lucky
- Fire dancers at the Pier 60 sunset festival
Episode FAQ
What is the Clearwater Beach sunset festival?
Pier 60 hosts a nightly sunset celebration on Clearwater Beach with street performers, vendors, and — in this episode — fire dancers performing as the sun goes down over the Gulf.
Where does Brian eat in this episode?
The featured stop is the Bait House, an independently owned dockside seafood spot that has served Clearwater for over 50 years, known for its drunken shrimp and fresh-off-the-boat fish.
Do they really see wild dolphins?
Yes — during a boat trip from the marina aboard the Damn Lucky, a pod of wild dolphins shows up to surf the wake around the boat.
Behind the camera
This episode is a Nidhogg Studios production.
We film, edit, and deliver The Wandering Bostonian ourselves — the same crew and process behind our documentary and series work for clients. If your brand has a story worth an episode, let's talk.
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