Drinking, Au Naturale

10 Eliot St, Cambridge, MA 02138 (map)

The home of the double cheeseburger and, often, hipsters, students and industry players whiling away the wee hours on Miller High Life, conducts a three-ring circus: the banquette-bumpin' downtairs, the jukebox-jumpin' upstairs and the pint-pourin' beer garden. The sharp, European-style paradise tucked within Harvard Square becomes a lively haven come warm weather, with outdoor draft lines, umbrellas for sun and lamps for lack of, and company high on the fact that they're drinking in a virtual Eden.

250 Hanover St, Boston, MA 02113 (map)

At Fiore's rooftop bar, you're on top of the world--or at least a good head and shoulders above the rest of the hoi polloi in the North End (physically speaking, of course). Smugly sporting the Italian neighborhood's only seasonal patio, the restaurant serves guests glassfuls of Prosecco and Chianti as they nibble on antipasti and gnocchi al pomodoro. Another option? Begin the night with an aperitif (toast the sky if you wish), and traverse local eateries on a progressive dinner. Go on, paint the town red-sauce.

361 Boylston St, Boston, MA 02116 (map)

Without fail, the crew usually ends up happy and late-night sloppy on the patio of Parish Cafe. Witness the forces mightily align: a bulls-eye Back Bay location, a crazy-creative full bar, permitted smoking, comically generous portions and a kitchen open until 1am (and patio until 2). And it's a handsome perch, with huge umbrellas, ample seating and just-enough elevation above the sidewalk. The Public Gardens are a stone's throw, as well as the light at the end-of-the-long-night tunnel.

200 Atlantic Ave (Marriott Long Wharf), Boston, MA 02110 (map)

There's really not much more to say than that Tia's is awesome purely on the existence of its prime, million-dollar, waterfront perch. But awesome, nonetheless. The sweaty, sultry, skin-baring festivities start from the moment the patio opens for the season, a-throb with pheromone-exuding bodies wielding their umpteenth beer. Come for a quaff, the cool breeze wafting off the harbor and unparalleled people-watching, but any higher expectations than that--you're on your own, my friends. Drink up!

79 Park Plz, Boston, MA 02116 (map)

Just to be on the safe side, wear your VIP pants when you step into this lush, secluded patio--because who knows what socialite tongues will be wagging? With the luxe surroundings, elegantly casual Italian food (mmm, gnudi ravioli) and courteous staff, you'll hardly feel like you're on a sidewalk in the middle of Park Plaza. Smoking's permitted, as well as a copious thirst for Peroni.