If you're looking for dinner with a view of the St. Louis Arch, then the answer is Cielo at the Four Seasons. Located on the Mississippi River, the restaurant overlooks a rooftop pool, making it easy to forget that you are in the heart of the Midwest. The modern Italian menu covers breakfast, lunch and dinner with dishes such as compressed watermelon salad with Grand Marnier, cardamom, ricotta and porchetta, as well as brunch complemented by a bottomless Bloody Mary bar. At night, cocktails take the same approach as food — unpretentious but superbly executed with unique ingredients such as duck-fat scotch and baked-apple bitters (999 N. Second St.).
Nearby, a more historic hotel hides a selection of culinary gems. The Cheshire Hotel is home to Basso, another Italian establishment with a more rustic approach. The basement gastropub specializes in wood-fired pizzas served at the stainless steel bar or in one of the cozy booths. Opposite the bar, long wood tables sit next to the open kitchen, where chef Patrick Connolly prepares crispy meatballs and steak Fiorentina. The hotel also holds a more upscale restaurant with a 1,700-bottle-deep wine list, as well as The Market, a casual cafe, and Fox & Hounds, a cocktail bar reminiscent of an English hunting lodge complete with a stone fireplace and extensive whiskey list (6300 Clayton Rd.).