San Antonio, Texas

A five-minute walk down the San Antonio River Walk from the historic Alamo, sits a watering hole that has been satisfying thirsty Texans since the end of Prohibition: The Esquire Tavern. Opening in 1933, just six years ahead of the groundbreaking of the River Walk, the Esquire prides itself on an upstairs brimming with historical swank and a downscaled downstairs that offers a more laid-back setting on the river at the tavern’s rear. Both levels boast a separate cocktail list; the downstairs claims a more uncomplicated experience, but like the upstairs, the house cocktails are likely to contain five or more ingredients, many from the classic prohibition era. No Seven and Sevens here.

The Esquire didn’t mind if the whole family got a bite to eat upstairs, so we did; I grabbed their meatloaf sandwich, which may not seem very sophisticated except with a beautiful classic cocktail in tow. Mine was a Warpaint- a heady concoction of Norwegian Aquavit, Beet-Tarragon Shrub, Herbsaint, Cocchi Americano, and fresh-squeeze lemon juice. Cindy’s cocktail, the Scrubby Collins, was equally involved- a mixture of blanco tequila, strawberry-basil black pepper shrub, and mineral water, stirred on ice and served long.

In true Wisconsin-style, I couldn’t leave without an after-dinner (or lunch, in this case) drink, so I ordered up a Waking the Dead #1 (yes, they did also have a #2 too, which was too fruity for my tastes). Although we don’t know the exact proportions, I do have the ingredients, so here’s my best approximations...

Drink: Waking the Dead #1
Establishment: The Esquire Tavern
Location: San Antonio, Texas
First Connoisseur: Holly

1 ½ ounces bonded bourbon
¾ ounce Italian vermouth (I used Carpano)
½ ounce espresso-fernet (I used a mix of espresso liqueur and fernet branca)
1 ounce pineapple juice
Dash of fresh-squeezed lemon juice

Place all ingredients in a shaker full of ice. Shake until chilled. Serve up in a cocktail glass and enjoy in warm temperatures.