Vintage
Terrific list, great by-the-glass variety. 14C Eliot St., Cambridge, MA .
Diamond Jim's, Hotel Lenox
Funky, with sing-alongs. Visiting theatrical folk often stop by. 710 Boylston St., Boston, MA .
Ryles
Makes a serious effort to book the best music. Watch for Bellevista. 212 Hampshire St., Cambridge, MA .
Harvard Bookstore Café
Not only that, you can meet pros like author Shelley Winters here, too. 190 Newbury St., Boston, MA .
Bin 26 Enoteca
With a selection that runs from aglianicos through zinfandels and a wine list that reads like a guidebook, Bin 26 is an unknockable choice for novices looking to get their palates wet. Seasoned oenophiles will likewise have no quibbles with the 70-plus wines by the glass and more than 200 by the bottle. The interior—swaths of cork and wallpaper made from wine labels—might have come off too clever by half in the hands of anyone but the design savants of Office dA, who make it feel quirky, warm, and more than a bit European. Indeed, Bin 26 gets it so right that after a few glasses, you may think you're looking out on a side street in Trastevere, not Beacon Hill. 26 Charles St., Boston, MA 2114, bin26.com.
Beehive
It's easy to agree on where to mingle if you and your posse are bent on skimming from the same pool, whether that's just-graduated daddy's girls (Foundation Lounge), martini-swilling cougars (Cuffs), or baseball-capped frat dudes (Clery's). Finding a pheromone-drenched locale that covers a variety of predilections is a much taller order. The South End's Beehive measures up nicely, drawing a clientele as diverse as its all-star team of bartenders and as tasty as the cocktails they stir up. And whether you're seeking a tattooed hairstylist or a sweater set-clad preppette, the uncharacteristically well-lit (for a bar) space means you'll get a clear view of your quarry. 541 Tremont St., Boston, MA 2115, beehiveboston.com.
KO Prime
Gazillion-thread-count sheets aside, a hotel is really only as good as its bar. And chichi steakhouse KO Prime has admirably elevated the one at downtown's Nine Zero Hotel over the past year. Adjacent to the restaurant's sweeping dining room, the loungelike space caters to an in-town audience as well as trysters and overnight guests with a smart by-the-glass wine list and wowza cocktails such as the green tea-calamansi gimlet (chilled with liquid nitrogen!). For travelers with work to attend to, the combination of wireless Internet and tush-pleasing seating banishes the memory of sterile hotel business centers. 90 Tremont St., Boston, MA 2108, .
Sunset Grill & Tap
Just reading the beer menu at the Sunset is enough to make your head spin. At last count there were 100 brews on tap here, as well as 300-plus bottled beers. The selection ranges from the prosaic (Pilsner Urquell) to the obscure (Stone's Arrogant Bastard Ale) to the unpronounceable (the Gueuze 100% Lambic is said to be the champagne of beers). For connoisseurs, there's usually a cask-conditioned ale, like the popular Middle Ages' Wailing Wench; for the less discerning, there are the always-reliable Bud Light longnecks. 130 Brighton Ave., Allston, MA 2134, allstonsfinest.com.
21 Federal
Much as we enjoy fighting for a bar stool with sunburned tourists and libidinous and over-lubricated college students, we do sometimes crave a slightly more civilized scene. 21 Federal, inside a classic Nantucket 1847 Greek Revival building, features a sophisticated downstairs bar and another cozy one upstairs. In-the-know Nantucketers congregate here for masterfully poured drinks; an award-winning wine list; good-looking, genial bartenders; and a crowd that knows how to have a stylish sort of fun. 21 Federal St., Boston, MA 21federal.com.
Wally's Cafe
A taste of what jazz was like before it was a cultural treasure and was still just a species of fun—and some of the most unpretentious entertainment Boston had to offer. Open 365 days a year: launched half a century ago. 472 Massachusetts Avenue, Boston, MA .
Luxor
Eschews trendiness and meat-market aesthetics for a laid-back neighborhood feel. Great videos, movies, and theme nights—not to mention a killer float in this year's Gay Pride Parade. 69 Church St., Boston, MA .
The Naked Oyster
Manhattan meets Cape Cod at this trendy Hyannis bistro and raw bar. The oysters—prepared naked or topped with a hint of cocktail sauce, a splash of Absolut Peppar vodka, or sour cream and caviar—are beyond divine. The littleneck clams are tiny tastes of the sea. And the melt-in-your-mouth beef carpaccio appetizer and a host of tempting desserts round out a fun, fresh menu. 20 Independence Dr., Hyannis, MA nakedoyster.com.
Sullivan's Tap
Consider yourselves warned: This place features the same rough-and-tumble ethic as the B's defensemen. Sure, there are other bars with superior viewing experiences, cleaner bathrooms, and more-refined crowds. But no one captures the spirit of the sport the way Sullivan's Tap does. Plus, the beer here is about as cheap as it gets. 168 Canal St., Boston, MA 2114, .
Davio's
Those who like their men as rich as a well-marbled rib-eye frequent this wood-paneled, martini-soaked Italian steakhouse packed with Mad Men wannabes, both of the divorced and the, ahem, forgot-my-ring-at-home variety. 75 Arlington St., Boston, MA 2116, davios.com.
Black Number Nine
The retro-bluesy rock of Black Number Nine will appeal to anyone who counts the Rolling Stones' "Exile on Main Street" or anything by the Black Crowes among their favorite albums.