Coffee is what originally brought me into Leaf & Bean. It’s a regular Key West oasis in the heart of the Strip. The walls, floors, and ceilings are covered in a smorgasbord of artifacts that fall somewhere between Iron City and island themes, many of which have been gifted to owner “Island Jim” Robison. He’s running out of room, but he won’t sell a thing—not the motorcycle, the bathtub, a barber’s chair, or even a tin sign. There are only two things for sale at Leaf & Bean: coffee and cigars.

This eclectic cigar shop is Jim’s childhood dream of a clubhouse becoming a reality—at just about the time he was ready to retire. Locals stop by to chat or read the paper on weekdays. People gather to celebrate the end of the workweek on Fridays. It’s a bonafide party on Saturdays. If you want to catch the live tunes (12-3pm), come early to snag a seat at the mismatched tables and chairs.

At Leaf & Bean. Photo by Janna Leyde.
At Leaf & Bean. Photo by Janna Leyde.

One afternoon, I dropped in for a pound of coffee and Island Jim and I bonded over the Buffett song that was playing (I have Parrothead parents and he’s lived that life in Key West). “Come back for the real experience,” he said. “Get your man, buy a growler, and have a cigar.”

That Friday, I returned with Chad and a growler from East End Brewing Company, which we put in the fridge by the door, and into the humidor we went.

I’m the kind of girl whose cigar knowledge is limited to articles in Esquire and puffs at weddings. Surrounded by hundreds of cigars, neither one of us knew how to choose. Mel, who knows a thing or two, introduced us to LEAF by Oscar. A good place to start, because there is no other cigar like it. Why? Cigars are wrapped in cello (cellophane). LEAF is wrapped in a tobacco leaf. Necessity is the mother of invention: Last year Island Jim was in Honduras, visiting Oscar Valladares’ factory and was in need of a wrapper for his naked cigar and used a tobacco leaf. Upon arriving home he discovered that the cigar was fresher and more flavorful than if it had been wrapped in cello.

And now? LEAF by Oscar (Valladares) has Cigar Aficionado intrigued, Cigar Authority rating it pretty darn high (92), and the head honchos of cigar companies yelling why didn’t someone on my staff come up with that? LEAF is also the most eco-friendly cigar out there.

LEAF by Oscar PhotoCred Janna Leyde
The many offerings at Leaf & Bean. Photo by Janna Leyde.

Chad went with the Connecticut wrapper, while I treated this like a craft beer order, hemming and hawing over notes and spice and flavor until I settled on Sumatra (over Maduro and Corojo). Later I learned that Island Jim stocks his humidor with 85 percent boutique cigars (made in small factories in Nicaragua and Honduras) and calls Leaf & Bean “the craft beer of cigars.”

We got our growler and found a table. Mel set her pearly white zippo down for us and attended to other customers. I failed three times before lighting it. I don’t smoke. I was nervous.

If you’ve never enjoyed a cigar, but you revel in specialty coffees, exotic teas, or microbrews, then make Leaf & Bean the next thing you do. The cigar was delectable. Not stuffy or suffocating, but flavorful, smooth, and it burned slow enough to remind me that Leaf & Bean was on island time.

“We’re in thousands of stores already.” Island Jim had pulled up a chair to share with us the enlightening and overwhelming experience of his falling into the cigar business at just about retirement time. “It’s not looking like any time soon.” With a rollicking clubhouse, a cigar in demand, and the Island Jim brand in the works, the man never gets a day off.

Get to know a little bit about Island Jim in this video. Want to hang out with him? Stop by Leaf & Bean or head down to Central America with him on a cigar factory tour.


Leaf & Bean in the Strip

2200 Penn Ave.

Pittsburgh PA 15222 USA


Mon-Wed: 7am-4pm

Thurs-Fri: 7am-6pm

Sat: 8am-5pm

Sun: 10am-3pm

Janna is happily rediscovering Pittsburgh after spending nearly a decade living New York City. She’s a writer by trade—magazines, blogs and a book called He Never Liked Cake. And she’s also a yoga teacher. Her classes can be found pretty much all around this city.