Though located at a busy intersection frequented by people who want to see and be seen, Brennan’s Wine Bar and Cigar Shop (4659 Maryland Ave., 314/361-9444, Mon.-Sat. 3pm-1am, Sun. 3pm-midnight, no cover) remains one of the best-kept secrets in St. Louis—many of the locals don’t even know about this outstanding wine and cigar bar. Perhaps that’s because this single address is home to four locales in one. You’ve got your main-floor wine and cigar storefront, which provides cash-and-carry wines by the bottle. During warm-weather evenings, the outdoor patio serves as an excellent post for people-watching, and on chilly winter nights, the basement speakeasy Scotch bar provides a welcome coziness. Finally, the second-floor Maryland House is popular with both the primped and the laid-back, offering wines by the glass, cheese plates, and a casually cool vibe.
Anyone can mix a drink or pour a glass of wine, but very few get to do so with a million-dollar view at their back. Bypass the ostentatious Lumière Place casino and hotel, glide through the meditative lobby, and slide into a sumptuous seat at Cielo Restaurant & Bar (999 N. 2nd St., 314/881-2105, Sun.-Thurs. 11am-11pm, Fri.-Sat. 11am-1am, no cover), the Four Seasons Hotel bar. Ah, sanctuary. This downtown destination plays host to footballers, St. Louis celebrities, and visiting luminaries alike, and the rooftop lounge offers stellar sights, impeccable service, and five-star sips.
A Wine Spectator Award of Excellence winner twelve times over, Remy’s Kitchen & Wine Bar (222 S. Bemiston Ave., 314/726-5757, Mon.-Thurs. 11:30am-9:30pm, Fri. 11:30am-11:30pm, Sat. 5pm-11pm, no cover) is a place that’s serious about good wine. The good thing is, no one here takes themselves too seriously; the decor is at once classy and whimsical, the servers have great senses of humor, and the wine list is well-cultivated and creative. It’s not uncommon to see a businessperson or professor tucked into a corner table, reading a book and working his or her way through a wine flight. The flights change monthly and offer sippers the opportunity to try some truly amazing vino. Summertime flights often include gorgeous Alsatian varietals, while winter flights showcase hearty Cab blends. The food at Remy’s is hit-or-miss, but you can’t go wrong with the cheese plate and the stuffed grapevine leaves.
Sasha’s Wine Bar (706 De Mun Ave., Clayton, 314/863-7274, Mon.-Sat. 11am-1am, Sun. 10am-midnight, No cover) is exactly the kind of hidden-away, low-key spot people seek out to unwind over a glass of wine (or three). Situated in a quiet, residential neighborhood you’ll wish you could call your own, Sasha’s faces a tranquil park, making its outdoor seating a perfect refuge from the city’s hustle-bustle. And when those patio tables are full, indoor patrons still can enjoy the benefit of a breezy summer night: The French doors are frequently flung wide, bringing the outdoors in. The lengthy wine list ensures there’s something for every palate, and the crepes, pizzas, and other small plates guarantee you won’t be drinking on an empty stomach.
The 33 Wine Shop & Tasting Bar (1913 Park Ave., 314/231-9463, Tues.-Sat. 3:30pm-1am, no cover)—33 to its regulars—is one of the city’s hidden gems, a beautiful (and smoke-free) bar with a tremendous wine list, friendly and exceptionally knowledgeable staff, and one of the funniest menus that you’ll ever read. The menu provides great choices at every price point, with only a modest markup if you enjoy a bottle (or two) at the bar. The beer selection is excellent, too. In nice weather, 33’s backyard patio is a lovely place to while away an evening.