Daniel Webster used to polish off a glass of brandy with every dozen oysters he scarfed down at the raw bar of the Union Oyster House (41 Union St., 617/227-2750, 11 a.m.–9:30 p.m. Sun.–Thurs.; 11 a.m.–10 p.m. Fri.–Sat., www.unionoysterhouse.com , $22–34), the oldest operating restaurant in the United States. Entrées including baked scrod and filet mignon are a bit overpriced, but worth it for the Olde New England ambience.
In stark contrast to many of Charles Street’s stuffier addresses, Beacon Hill Bistro (25 Charles St., 617/723-7575, 7 a.m.–10 p.m. daily, www.beaconhillhotel.com/bistro , $24–29) is an easygoing (but still upscale, mind you) bistro serving French stalwarts like steak frites alongside creative constructions such as skate with spinach and sunchokes.
The owner of Ristorante Toscano (47 Charles St., 617/723-4090, 11:30 a.m.–10 p.m. Tues.–Fri.; 11:30 a.m.–11 p.m. Sat.–Sun., www.toscanoboston.com , $13–36), Vinicio Paoli, is Tuscan to his core—and so is his eatery. No daredevil renderings here: The kitchen keeps it real with simple dishes of carpaccio and penne arrabbiata.
Who knew that one of New England’s most Yankee neighborhoods was a prime place to experience the charms of Persian (that’s Iranian to you) cuisine? Grab a table at refined, pretty Lala Rokh (97 Mt. Vernon St., 617/720-5511, 12 p.m.–3 p.m. daily; 5:30 p.m.–10 p.m. daily, www.lalarokh.com , $14–19) to dig into a menu loaded with rose petal–scented dishes, kabobs, and fruit-laden sauces. And don’t miss the saffron ice cream.
One of the area’s most affordable lunches is found at Panificio (144 Charles St., 617/227-4340, 8 a.m.–10 p.m. daily., www.panificioboston.com , $7–23), where you can snag an overstuffed sandwich—on, as the name suggests, great bread—and salad for under $10. At night, the bakery turns more posh: Candles are lit, prices go up, and dishes get more elaborate—à la lobster penne and gnocchi marinara.