DRINK: Drinking Among Saints (& Sinners)

From chichi boutiques to high-end restaurants, of all of the neighborhoods surrounding the city’s urban core, perhaps none has a better reputation amongst those with a predilection for the finer things than San Marco. And in the past few years, a slew of upscale cocktail joints has moved in to provide reasonably priced libations to both the neighborhood’s proletariat workforce as well as its bourgeoisie clientele.

San Marco now mixes the best of both drinking worlds, the old and the new. There are dive bars, good restaurants, a movie theater, and now some classy watering holes. And it’s one of the most walkable (and easily cab-able) neighborhoods in the city. So whether you are looking for a high-end Sazerac or a Miller High Life, San Marco is a great place to throw one (or a few) back. 


We’ve seen this before. Edison light bulbs? Check. Exposed-pipe ceiling? Check. Dim lighting, communal tables, reclaimed wood? Check, check, and check. So bring on the expensive craft cocktails, right?

Not so fast.

Sidecar, on Hendricks Avenue, may have the look of a Roaring ’20s prohibition-subverting speakeasy, but it’s no secret they’ve got one of the best happy hours this side of the St. Johns. Each afternoon, Monday through Friday from 4 to 7 p.m., Sidecar offers up $6 classic cocktails (your Manhattans, your Old Fashioneds, your Vespers) as the urban core post-work crowd undoes a proverbial top button, loosens their collective proverbial tie, and waits for the very real traffic surrounding Downtown to subside.

Bartender Robert says he makes more Old Fashioneds than anything else and that any duo who orders an Old Fashioned and a Moscow Mule is very likely to be on a first date. Old Fashioneds have been one of the main engines driving the resurgence of craft cocktails across the country, and the drink has become not a must-do, but a must-do-well for any establishment seeking credibility. Sidecar’s version is straightforward and simple (the way it should be), but a little on the sweet side. If you prefer the taste of rye whiskey over citrus, the Sidecar’s Sazerac is a good choice.

Grape & Grain Exchange

One of the best things about Grape & Grain Exchange (located on San Marco Boulevard, in the heart of San Marco Square) is that it allows patrons two relatively upscale, yet down-to-earth experiences in the same place. The front part of Grape & Grain — whether lit up by late-afternoon sunshine or the streetlights on the square — is bright and open. A bar and several hightops, perfect for sharing a bottle of wine and some charcuterie among friends, give the place a communal feel. Walk toward the bookshelves in the back and you’ll be met with a much darker, much more intimate experience, with velvet curtains, candlelit hightops and another bar, backed by a masculine dark wood mantle. Regardless of where you choose to settle, the drink offerings are exceptional.

Tripling as a retail shop, Grape & Grain Exchange offers a well-curated selection of wines. The drink menu consists of classic cocktails (Manhattan, Old Fashioned, Hemingway Daiquiri), a rotating seasonal cocktail, and a selection of local beers on tap. Quadrupling as an entertainment venue, the back (darker) portion of Grape & Grain (known as The Parlour) often hosts local jazz musicians.

Though not technically in San Marco(and though the shows don’t necessarily carry on late into the evening), the Listening Room at Mudville Grille in St. Nicholas offers patrons a distinctive and sincere musical experience. Local music man Ray Lewis books Americana acoustic singer/songwriters to play intimate shows for attentive listeners. Lewis also invites touring international Celtic, bluegrass, jazz, and blues bands to play the Listening Room. And Mudville is a sports bar — with a liquor license — so how intimate and/or how attentive you plan to be during the performances depends entirely upon your ability to hold your alcohol.

Located just a stone’s throw from the Fuller Warren Bridge on San Marco Avenue and demarcated by eye-catching vintage, catawampus signage and striped awnings, Sherwood’s announces its social status in not-so-subtle ways; they are a dive bar. This is obvious from at least a football field away. And they are unapologetic about it.

The interior is Reno-truck-stop-chic with light-faux-wood paneling, perfectly counterbalanced by Michelob chandeliers. Everything is a deal here. $3 Tall Boys, $1 pool, $3 well drinks and, like any good dive, Sherwood’s allows visitors to indulge in many vices: gambling, smoking, drinking, Big Buck Hunting (in HD), and the most sexually suggestive skee-ball machine this side of First Baptist (a score of 400 or better is worth a free beer).

About EU Jacksonville

october, 2021