To Eat: Places like Olive's, Biba, Le Bettola and Mistral have all been written up in the foodie mags and for good reason. CD Rich Herstek also suggests Aquitaine and 9 Park as great spots. For something considerably less glam, try Tim's Tavern on Tremont St. -- an absolute dive with the best cheap burger you'll ever eat. ACD Nick Kaldenbaugh suggests lobsters at Woodman's in Essex, just North of Boston -- you sit outside at picnic tables and make a mess. It's great.
To Drink: A martini at the Ritz overlooking the Public Garden is kind of a classic Boston thing to do, but the martinis at the Oak Room in the Copley Plaza are probably better. A trip to the Middle East in Cambridge is a must, says AD Matt Rockett -- great drinks and a legendary spot for live music. (Some of the best bands to come out of Boston got their start here.) Christina Kleindienst, our resident nightlife expert, swears by Sophia's, 1270 Boylston -- live Latin jazz and pitchers of sangria. CW Brian Merrill's fave is Anchovie's at 433 Columbus Ave. -- cheap eats, great bar, a hangout for South End locals. CD Pete Favat and others recommend following this up with a trip down the street to Jacques in the South End for the late night drag show. Bring plenty of singles to tip the "ladies."
To Hang: On a spring night, Newbury St. is a must. Park yourself at one of the hundred outdoor cafes and people watch. CD Alan Pafenbach and AD Rachel Houk-Seeger both rave about the Maparium at the Christian Science Center -- a giant, inside-out glass globe of the world that you walk inside. The courtyard of the Isabella Stewart Gardner Museum at 2 Palace Rd. is spectacular. It's also the site of the biggest art heist in the U.S. (still unsolved). The courtyard of the Boston Public Library is a great oasis, and you can even bring a sandwich. And, of course, the cheap seats -- the bleachers at Fenway Park. But don't root too hard for the Red Sox. They'll break your heart.