Gentleman, we understand that not everyone wants to accompany their lady to the spa or perhaps an afternoon tea. We recognize that Saturdays are indeed for the boys. We also know that the majority of you hate planning, that’s why we’re making it easy. So easy that we don’t want you to plan a “getaway” or a “boy’s night out” we simply just want you to do. Please enjoy this city guide explicitly crafted for you (and yes, it’s all doable in a weekend, we checked.)

Don Alans

If you’re trying to look dashing and dapper, Don Alans is the place to begin. Carrying both casual and formal wear, Don Alans is dedicated to provide timeless pieces for the sophisticated man. One of the newer brands, Mizzen + Main, is one of Don’s favorite brands to talk up as they offer dress shirts that are made of performance fabrics that make them feel extremely comfortable. Plus, you don’t have to iron them!


Old Hickory Whiskey Bar


Old Hickory’s relaxing and engaging atmosphere make this one of the more interesting bars in the city. With over 600 whiskeys and other spirits, it’s hard to find something that you won’t like. My suggestion, get something that you see on one of the top shelves. A moving ladder spans the back side of the bar that staff so eloquently shuffle up and down upon on request.


Esquire Barber Shop


In a small red, white and blue - painted storefront near the corner of Palafox and Garden you'll find the oldest barber in Florida and one of the oldest barbers in the world! Joe Brown began cutting hair at the famous Hotel San Carlos in Pensacola during the Great Depression and has never looked back. Don't let the 101-year-old title fool you; he's one of only two people at the establishment that performs the daunting straight-razor scalp shave. Step in, sit back and relax on this nostalgic journey.


Wilfrid’s Barber and Fine Goods


Subsequently, if you’re looking for something a bit more trendy and modern, jump to the other side of Garden Street to Wilfrid’s Barber and Fine Goods. If you’re not in need of a suave haircut, I suggest the shave. A straight razor service, this luxury is an hour long and includes hot foam and a steamed towel. As for the fine goods, you’ll find salon-quality products such as beard oils and balms, repurposed skateboard beard combs, leather goods, soaps and candles.


Perfect Plain Brewing Co.


The newest addition to the micro-brew scene in Pensacola, Perfect Plain is a delicious piece of working history. The name “Perfect Plain” was coined by Rachel Jackson, wife of future president Andrew Jackson’s when describing Pensacola to a girlfriend back home upon arrival. “Pensacola is a perfect plain, the land nearly as white as flour” she wrote. There is something in it so exhilarating, so pure, so wholesome; it enlivens the whole system.”

Inside you’ll find an open-air taproom with long, communal tables and its entire 10-barrel brewhouse. And to drink, some of the finest ales of the south. They typically have six regular beers on tap with special occasion beers added for watch parties and events and other seasonal ones added as local ingredients come through. On Saturdays, you can expect a pop-up doughnut shop and yoga on the patio.

Cigar Factory Social Club

Originally from New Orleans, the Cigar Factory has quickly gained momentum in Downtown Pensacola. Offering a full bar and hand-rolled cigars, you and the bros can settle in the blush indoor seating or on the suave outdoor patio. If marriage or any other special occasion is in the near future, they have a sizable event space and also offer discounts on cigar boxes.

Now wasn't that fun? We think so too. In case you stumbled upon something noteworthy in your journey that wasn't mentioned, tell us in the comments below.