Eating Up San Antonio: La Gloria, The Monterey and The Esquire

Categories: On the Road

San Antonio 037.jpg
Rouse, Sedillo and my boyfriend all warned me that I couldn't leave San Antonio without a cocktail at The Esquire Tavern -- even if that meant leaving San Antonio for Houston at 1 a.m. -- and after that visit, the bar is now firmly on my must-visit list for every single future trip. Built in 1933 to celebrate the end of Prohibition, the bar has been open ever since (with a brief hiatus from 2006 to 2011) and was recently nominated for a James Beard Award for Outstanding Bar Program.

Almost everything inside and out at The Esquire is original, from the nailhead wingback barstools to the mirrors that line the back of the bar. The rear patio overlooks the Riverwalk, while the large space at the end of the L-shaped room hosts taxidermied animal heads and local bands, such as the Willie-Nelson-by-way-of-Lyle-Lovett-style quartet that was drawing applause on Tuesday night.

The cocktail program features old favorites like the Blood and Sand as well as creations that are all The Esquire's own: Try the Mexican-influenced La Bruja, with tequila, mezcal, averna, punt e mes, black currant and bitters, or the boozy Philly Smash with rye whiskey, averna, lime, sugar and berries in a mezcal-laced glass.

Toward the end of the evening, the diverse crowd inside The Esquire gave way to an elderly gentleman in a white seersucker suit and straw boater hat who plucked a young girl from his table and began to dance with her to the lulling strains of the quartet, who were winding down for the night.

"No matter what any of us do in life," remarked Sedillo, "none of us will ever be as cool as that guy." It was close to midnight and last call, so we closed up our tabs and walked back into the humid San Antonio night with promises to meet up again at The Esquire soon, which means I'll be making another short drive down I-10 west in a few weeks. I can't wait.



Follow Eating Our Words on Facebook and on Twitter @EatingOurWords

My Voice Nation Help
14 comments
Johncmata
Johncmata

Tables were switched out in late spring at are all wooden tops now over at the Monterey.

RebeRese
RebeRese

The man in the video is Mike Casey - local art patron and southtown godfather.  Late Tuesday I happened to swing by The Esquire for a night cap with friends and saw him on our way out.  They were celebrating his birthday.  That aside, The Esquire is a legendary place and it's rumored that JFK drank there the night before he died.

Rexster314
Rexster314

Whew!! I was worried. Back in the day (20 some odd) we drove from SA back to Houston after an afternoon of margaritas at La Fogata. Didn't remember leaving SA until we got to Flatonia and stopped in Grumpys (now closed)

Katharine Shilcutt
Katharine Shilcutt

That would be my boyfriend, who graciously stayed sober as a bishop so that I could enjoy San Antonio's bounty.

Rexster314
Rexster314

My only question is: After all the food and imbibing of spirits, who drove back to Houston at 1AM in the morning?

Debbie Weatherford
Debbie Weatherford

I am going to San Antonio this weekend and will take this article. Thanks. Can't wait to try some of the places you recommended.

lauren covington
lauren covington

hooray for this article! SA often gets overlooked.. people love to call it lame, but it really is so lovely and laid back. we look for any excuse to get out there!

Nicholas Dion
Nicholas Dion

The Monterey is amazing. San Antonio's version of Austin's Barley Swine. I wish Houston would catch up. And no, Hay Merchant is not close.

Terry Alexander
Terry Alexander

The Esquire is a cool place. They have one of the biggest Door Lords in San Antonio. Cool guy. I almost walked out on our drinking companions last time we visited when he asked for a Coors Light. TA

Dorothy N. Nelson
Dorothy N. Nelson

Hotel Havana. It's got an amazing patio and such a cool vibe...DemoforFrank.blogspot.com

Jalapeno
Jalapeno

I guess that break-up diet worked wonderfully!

Katharine Shilcutt
Katharine Shilcutt

No, but Dough and Gwendolyn are both on my to-try list for the next visit!

Tara
Tara

Dough is excellent. Gwendolyn is meh...I wouldn't go out of my way to go there. Other great places are Bliss (owned by Chef Mark Bliss) just across the parking lot from The Monterey, Il Sogno (owned by Chef Andrew Weissman) in the Pearl, Sustenio (Executive Chef David Gilbert) in the Elian Hotel way out by The Rim at 1604 & I-10, & Luke, a John Besh restaurant that has Chef Stephen McHugh at the helm.

Now Trending

From the Vault

 

Loading...