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This casually upscale drinking patio takes up roughly a third of the Roosevelt Hotel’s nineteenth-floor rooftop. The large space is strewn with lacy cabanas, high café tables, and slatted wooden benches. The bar peeks out of one corner, concession-stand style. Rows of well-manicured arborvitaes line the walls. After work, an older, finance set dominates and, while the drink prices reflect flush wallets, the cocktails work hard to earn their price tags: Try the Teddy-tini with chilled espresso and coffee-bean garnishing or the Chocolate Martini with vanilla vodka and Dark Godiva. — Ben Lebeaux