On a weeknight, the walk from a Pen Key Club driveway to a dinner reservation covers less ground than the walk from a parking spot to a grocery store. Out the gate, past the hedge line, and the hostess stand at Ziggie & Mad Dog's is already in view. Most residents make that walk without giving the building itself a second thought.
They should. That building has been selling Pen Key Club since before Pen Key Club had homes to sell. Long before it started plating filets and lobster bisque, it processed the paperwork that put the community's first owners behind these same gates.
A Pineapple Outbuilding Becomes a Sales Office
The structure at 83000 Overseas Highway started life in the 1930s as an outbuilding on a pineapple plantation, one of the small support buildings scattered across Upper Matecumbe Key before the Keys economy shifted from agriculture toward tourism and sport fishing. When Pen Key Club began selling its bayfront lots, that same building was converted into the club's sales office, the place where paperwork for the gated community's earliest homesites got signed. By the 1950s it had changed again, into a small restaurant, years before anyone had heard the name Ziggie's.
Every gated community has a founding office somewhere. Most keep theirs as a filing cabinet or a plaque. Pen Key Club's became a steakhouse and never closed.
Ziggie Stocki's Conch, and the Company It Kept
In 1962, a gambler and drifter named Ziggie Stocki bought the property for $100,000 and opened Ziggie's Conch. By then the building's back rooms already carried a reputation. The Miami Herald reported on police confrontations with a group referred to as the new Capone gang as far back as 1948, and stories persist that Al Capone himself sat in on high stakes card games once held there. Director John Huston is said to have gotten the idea for his 1948 film Key Largo while gambling at a casino Ziggie frequented, which puts this particular address closer to the source of one of the more durable pieces of Keys folklore than to a footnote of it. Whatever separates fact from legend in that claim, the building has never moved from where the story places it.
Mad Dog's Renovation
In September 2005, former Miami Dolphins tight end Jim "Mad Dog" Mandich and his business partner Randy Kassewitz bought the property. Mandich had been part of Don Shula's undefeated 1972 Dolphins team, and after seven months of renovation, the building reopened on April 15, 2006, under a new name: Ziggie & Mad Dog's. The team kept the original bar, the slate wainscot, and the terrazzo floors intact rather than starting over. Mandich died in 2011, but the restaurant he restored is the same one Pen Key Club residents walk to tonight, the same terrazzo under different chairs, the same footprint that once held a sales counter instead of a bar.
Out the Gate, Toward Mile Marker 82
The gate at Pen Key Club sits between Ziggie & Mad Dog's on one side and the History of Diving Museum on the other, so the walk in either direction starts with a landmark. Continue south past the museum and the road runs into the Morada Way Arts & Cultural District, the stretch of Old Highway between mile markers 81 and 82 that's home to a run of Islamorada's better-known restaurants, all within easy walking distance of each other:
- Kaiyo Grill
- Chef Michael's
- Ma's Fish Camp
- Green Turtle Inn
- Islamorada Fish Company
- Morada Bay Café
- Pierre's
Florida Keys Brewing Company anchors the district's evening crowd with an outdoor beer garden that draws as much foot traffic as any of the restaurants around it. For anyone eating further down the highway than a comfortable walk allows, the Village runs a free Freebee electric shuttle, so even the restaurants outside easy walking range don't require pulling a car out of a garage.
The Third Thursday Habit
Since 2011, the Morada Way Arts & Cultural District has hosted its Art Walk on the third Thursday of every month, six to nine in the evening, with gallery openings, live music, food, and artisan vendors filling the corridor between the museum and Florida Keys Brewing Company. Local painter Jessica Ann shows work at two locations along Morada Way, and Key Largo native Taylor Hale keeps a studio tucked behind the brewery's beer garden, where he paints the interplay of water and light he grew up watching from the water itself. The next one lands on Thursday, September 17, 2026, close enough that it's worth putting on the calendar now rather than discovering it by accident on a Thursday drive home.
A Longer Table in October
Islamorada Restaurant Month returns October 1 through 31, 2026, a month-long run of prix-fixe menus, chef showdowns, and beachfront dinners across the Upper Keys. For residents inside Pen Key Club's gates, it's a rare stretch where the neighborhood's own walkable restaurant row runs a coordinated calendar of reasons to book a table without needing to drive anywhere at all.
The building at the gate has spent nine decades changing what it sells without ever changing what it's selling for. First it moved dirt and deeds. Now it moves steaks and reservations. Either way, it's still the first thing you see stepping out, and still the reason people keep walking toward it.
Curious what else is quietly woven into the history of the Upper Keys neighborhoods you already call home, or thinking about a move to one? The Florida Keys Sold Sisters know these streets, docks, and dinner tables better than most. Start Your Island Home Search — Schedule a Personal Consultation.
