Bank of America Pavilion
This is not the place to go to make some great new musical discovery—the Pavilion's schedule remains heavy on well-known arena rockers. But there's no better spot to catch your favorite '80s band than this open-air venue, especially once the sun sets, the breeze picks up, and you settle in with a couple of frosty beers. Bonus: As Boston's waterfront continues to develop, so do the Pavilion's pre- and post-show drinking and dining options, such as Morton's, Legal Test Kitchen, and Atlantic Beer Garden. 290 Northern Ave., Boston, MA 2210, bankofamericapavillion.net.
Anna's Taqueria
The true test of a good burrito is: Will you travel for it? In Boston, burrito lovers have little choice. This is, after all, a city with a whole lot of average Mexican food. To find an affordable burrito worth eating, we recommend taking any and all forms of transportation to one of Anna's Taqueria's three area locations. The restaurants are clean, the service is speedy, and the food is fresh. And the burritos? Well, they're so big and tasty, you might just forget you're in Boston. 1412 Beacon St., Brookline, MA annastaqueria.com.
Ginza
This is where Boston's other sushi chefs eat on their nights off. Memorable maki comes with ingredients ranging from burdock root to Japanese basil. The fish is unbelievably fresh, the presentation stunning, the extra-long hours ('til 4 a.m., Tuesday-Saturday) convenient. 14 Hudson St., Boston, MA .
Ristorante Toscano
Crosstown rivals in the North End have yet to equal the confident simplicity of veteran chef Venito Paoli's cuisine. Paoli turns out matchless risotti, superb seafood, and Boston's best Bolognese sauce. If Italian cooking guru Marcella Hazan came to visit, you'd take her to Toscano. 41 Charles St., Boston, MA .
Club Cafe
With brunch, trivia, late-night drinks, dancing, and a solid crowd of regulars, Club Cafe has it all. For decades, this place—at a prime intersection of the Back Bay and the South End—has been the Cheers of Boston's gay scene, and it's easy to understand why. 209 Columbus Ave., Boston, MA clubcafe.com.
Shred
Boston's fitness studios offer just about every workout under the sun. But to take SurfSet—a boot-camp-style class held on mock surfboards that simulates the feeling of being on water—you have to visit this three-year-old spot in Quincy. Once you finish blasting your core on the boards, head back to solid land for Shred's Spinning, reformer Pilates, and mat Pilates classes. 453 Washington St., Quincy, MA 2169, shredbody.com.
The Big Quiz Thing at Oberon
Bar trivia is a tricky business, but the Big Quiz Thing has the formula down. The free monthly event at Oberon offers kitschy graphics, quirky categories, and appropriately mind-lubricating beverages. Hence, it's the closest analogue to a game show on Boston's nightlife circuit, right down to the final round, where high-performing teams square off in a sudden-death buzzer challenge. 2 Arrow St., Cambridge, MA 02138, bigquizthing.com.
B & R Artisan Bread
Seeing as how first impressions are everything, a restaurant's bread-basket is serious business. Boston's finest eateries, including T. W. Food and Troquet, order their loaves from Sel de la Terre alum Michael Rhoads, who bakes crisp baguettes, hulking sourdoughs, and authentic ryes in his two-year-old Framingham shop. City-dwellers, meanwhile, can fight over B&R's pain levain at Cambridge's Formaggio Kitchen or the Union Square farmers' market. 151 Cochituate Road, Framingham, MA 1701, brartisanbread.com.
Liz Caan Interiors
Exuberant (think: Miles Redd) and exacting (as in, David Hicks), Liz Caan has expelled boring beige from the palettes of Boston's elite interiors. (And just in time, because we were running out of synonyms for oatmeal and ecru.) With a flash of fuchsia and couture flair, she turns every space into a chic party—approved by Brahmins and bankers alike. 1066 Centre St., Newton, MA 2459, lizcaan.com.
Radius
On any given afternoon, this sophisticated circular dining room is a discreet midday Who's Who of dealmakers and deal breakers. But it's not all business. Boston's power elite flock to be wowed by chef Michael Schlow's food, from steak tartare to smooth-as-silk soups and elegant entrées like roasted halibut with puréed cauliflower, giant lentils, and a Spanish paprika sauce. No matter how tempting the three-martini lunch might be, business discussions these days are brisk, and Schlow's speedily delivered cooking fills the bill. 8 High St., Boston, MA radiusrestaurant.com.
Ares Shoe Repair
Ares has been resoling, reheeling, and repolishing Boston's finest leather shoes for more than 70 years and will take extra special care of yours. The expert cobblers in the cozy basement storefront are a serious but likeable bunch who each have years of training behind their knowledge of the craft. That expertise means they can resize, stretch out, clean up, or de-scuff just about anything you bring in—fast, and at a reasonable price. 84 Charles St., Boston, MA .
Grill 23 & Bar
Let the newcomers show off their newfangled steakhouse specialties; people who really love steak will always return to Boston's exemplar of the genre. Here you'll find dry-aged, bone-in chops and tenderloins that drip with flavor in each juicy bite. The vibe—gold rails, leather banquettes, white-coated waiters—is classic without seeming clubby. 161 Berkeley St., Boston, MA 2116, grill23.com.
Chocolee Chocolates
With her jewel-like bonbons (exhibits A and B: dark chocolate filled with white chocolate and Chambord, and wafer-thin Viennese almond bark), Lee Napoli has brought a new level of artistry to Boston's confectionery scene. It's not just that the flavors are fresh as can be; Napoli's creations look gorgeous, too. Stop by the South End shop on a weekend morning for a trio of fried-to-order beignets oozing, naturally, with warm, luscious chocolate. 23 Dartmouth St., Boston, MA 2116, chocoleechocolates.com.
Cuffs—An Irish Bar
Most Boston hotel bars are party playgrounds for visiting movers and shakers. But for those jaded by the jet set, there's Cuffs at the Jurys Boston Hotel, where the scene is all seductive ambiance and ruby-red martinis. A superchic local clientele packs the joint every Saturday night, lured by the trickling waterfall, glowing fireplace, and hearty pints of Guinness. 350 Stuart St., Boston, MA .
Lewis Interiors
Polly Lewis and Maribeth Brostowski are carefully guarded secrets among Boston's glitterati. The designers have incredible taste and restraint, and we adore their pluck. Just one example of their fine work: They recently outfitted a Beacon Hill townhouse's library with wainscoting, deep crown moldings, and predictable muted grays, but made it extraordinary by painting the walls a superslick (and completely awe-inspiring) candy-apple red. 31 Gloucester St., Boston, MA 2116, lewisinteriorsboston.com.