HAPPY HOUR HAPPENS with Josh Wagner & Alan Philips: Gramps Getaway Key Biscayne, Miami

Volume 01: Gramps Getaway, Key Biscayne

Welcome to Happy Hour: Make the Miami You Want — our new content series in partnership with Josh Wagner, where we explore the best happy hours across Miami and spotlight the different energies, people, and venues that make this city electric.

In each episode, we’ll visit one local spot and let the moment unfold — real conversations, cold cocktails, and the kind of hospitality you don’t find on a press release.

First up: Gramps Getaway in Key Biscayne. Burgers. Beers. Daiquiris. Stories. And a proper welcome to the Miami you actually want to be in.

What Happened at Gramps

Josh was already at the bar. Alan showed up late. Miami history lessons were exchanged over drinks. And Derek the GM, mustache and all, took us on a ride, serving up oysters, shrimp dip, daiquiris, and a backstory on a legendary local named Jimbo, who lived to 100, refused to conform, and built a lifestyle most of us are still trying to catch up to.

We didn’t just sip cocktails. We learned what it means to drink with context. We talked about Miami’s emotional geography. And we remembered that the best kind of hospitality is the one that doesn’t try too hard, it just shows up.

Highlights from Episode One

Happy hour is about how you feel, not what you pay.
“Don’t get excited by the price,” Josh said. “Get excited by the possibilities.”

Miami is a city of energy shifts.
Cross a causeway or a boulevard, and it feels like a different city. That’s the magic.

Gramps burger might be the best in the city.
Not a sponsored statement. Just a real one.

Jimbo was the original Miami local.
Before influencers. Before fancy. Just good vibes, great seafood, and no shoes.

Daiquiris deserve more respect.
Cold, simple, and finished in three sips. It’s the signature smile of any happy hour done right.

Hospitality Advice from the Other Side of the Bar

We asked Derek what separates the good guests from the bad ones. His answer?

“Acknowledgement is everything. You don’t need to wait forever. Just respect the process. If someone says give me 20 seconds, give them 20 seconds.”

It’s that simple. Respect earns respect.

The Facts: Gramps Getaway

You can park your boat here. Spend a lot and don’t pay to park ;)
Jimbo’s Brew is a must have & get custom merch designed by Sun & Suns.
It’s the sister property to legendary Gramps in Wynwood
Book a tour with the local shark taggers. Yes there are a lot of sharks out there. Don’t be scrrd.
P.S. Happy hour makes you happy.

Why This Series Matters

This isn’t about a list of where to go. It’s about who makes this city worth staying for. The bartenders. The cooks. The stories. The energy. The sense of place you can’t fake.

Every week, we’ll keep chasing the happy hour that reminds you why you’re here in the first place. Miami is what you make of it.

So make it count. Make it yours. Or as Alan says, “Make the Miami you want.”

New episode coming soon to a Substack or social channel near you.