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The patio at Parson's Chicken & Fish is enormous, though the long picnic tables aren't ideal for private conversations. Up until today the restaurant didn't serve food outside, which made it fairly easy to get a seat there for drinks, but this evening they're going to start seating people at outdoor tables for dinner. It'll be nice to be able to get some fried chicken while drinking outside, as long as the crowds don't make sitting on the patio at all completely impossible.
Anyway, assuming you can get a seat, the much-hyped negroni slushy is probably the drink to order. Most frozen drinks I've tried elsewhere are sickly sweet, but this negroni—made with Letherbee gin, Luxardo Bitter, sweet vermouth, and citrus—is just the opposite, bitter and complex. There's something about bitter drinks in hot weather that just works, the same way IPAs always seem most appealing in the summer. The fact that the drink has been made into a slushy solves the problem of ice melting too quickly in the heat and diluting your drink, which is probably a good thing since it's boozy enough that drinking it too fast could be dangerous. For groups (or ambitious couples), it also comes in a one-liter carafe.
Scofflaw's outdoor area is much smaller—it's the fenced-off sidewalk variety rather than a true patio—but the drinks still make it worth a trip. My favorite of the cocktails I've tried recently is the Runaway, with Rittenhouse rye, Bonal quinquina, lemon, grapefruit, and raspberry syrup. The syrup gives the drink a nice magenta color and a fruity flavor that blends nicely with the whiskey. There's only a slight sweetness, which is balanced by the rye and the lemon.
The patio at Big Star, of course, is one of the best in the city—and impossible to get into unless you go before about 5 PM on a weekday. But that's what vacation days and long lunches are for. I usually order the Paloma (blanco tequila, grapefruit, lime, Mexican Fresca), which is less sweet than the margaritas. But they recently introduced the Ramblin' Rose, a summery cocktail made with mezcal, blanco tequila, strawberry, mint, cucumber, and lime that's pleasantly fruity and even less sweet than the Paloma, and will definitely be my go-to as long as it stays on the menu. I was also pleasantly surprised by the Bakersfield Buck (Heaven Hill bourbon, lime, Gosling's ginger beer)—I don't always think of bourbon for summer cocktails, but the ginger beer and lime make this perfect for warm weather.