Sasha's on De Mun (706 De Mun Avenue; 314-863-7274)
Sasha's park-front De Mun location is the perfect place to congregate when you want to sneak out of work and celebrate the day with a glass of wine and a cheese plate. The atmosphere is stylish but humble, featuring the requisite doses of glass block, exposed brick and handmade wine racks. The list contains more than 60 wines, all available by the bottle, glass or 1.5-ounce taste. Build a foundation from the ample selection of house-made soups, salads and sandwiches or -- go ahead, you deserve it! -- splurge on caviar and a bottle of Champagne.
Cielo (999 North Second Street; 314-881-5800)
You could, of course, go up in the Arch if you're seeking out a great view of the city, but you might notice a couple important things missing from your view -- specifically, our iconic landmark itself, a gentle Midwestern breeze and (most importantly for this list) a cocktail. Cielo's sprawling patio, located on the eighth floor of the Four Seasons Hotel, provides the perfect setting for falling in love with the city over a daytime beverage.
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