In Episode 9 of On the Bar Fly, we head back to one of our all-time favorite vacation spots — Key West, Florida 🌴🍹

If you’ve never been, go. Seriously.

Key West is like Vegas without the gambling and desert — sunshine, cocktails, characters, and just enough chaos to let you forget who you’re supposed to be for a while. From fake tattoos gone very wrong to a surprise encounter with Darth Vader, this trip delivered exactly what Key West does best: stories.

We mostly behaved… and somehow made it home with most of our dignity intact.

We talk about why we love the Keys, what makes Key West such a perfect escape, and why some places give you permission to loosen up, laugh at yourself, and lean into the moment.

Grab a drink and travel On the Bar Fly with us.