Chez Henri
Harvard Law students flirt with hipster artists at the bar. Undergrads flirt with their first taste of grilled octopus in the dining room. Software publicists pitch clients in the bistro's corner, between gulps from the smartly chosen wine list. And the best part is that everyone is genuinely, utterly relaxed. Does Harvard Square get any more real than this? One Shepard St., Cambridge, MA 2138, chezhenri.com.
Bouclé Salon & Spa
On the second floor of a restored gray-shingled Edgartown Colonial lies an unlikely retreat. Bouclé may not be posh, but it has a gracious staff and ample charm in creaky floorboards, not to mention an extensive list of fairly priced services. Expect relaxing deep facials and cosmopolitan haircuts, as well as long-lasting manicures from the new nail care cottage in the backyard. Bumble and Bumble take-home treatments and flirty silk hair accessories for sale make leaving Bouclé with a shopping bag or two under the arm almost as much fun as walking in. 12 N. Water St., Edgartown, MA 2539, bouclespa.com.
Lucky's Lounge
A lounge used to be a place where you could mingle with strangers and tie one on at any time of day. Now it's usually just home to overdressed scenesters and overpriced drinks. But Lucky's is a throwback to the glory days. A speakeasy-style bar with dim lighting, vintage leather booths, and walls covered in Rat Pack photos, it's an ode to the three-martini lunch era. 355 Congress St., South Boston, MA 2210, luckyslounge.com.
Rangoli
The prized entree at this southern Indian restaurant is called dosa—a huge crunchy crepe stuffed with rice, lentils, and your choice of meat. But that doesn't mean you should neglect the dahi bhala (lentil balls and yogurt) or the tomato-coconut shorba (soup). The chef works with a cunning palette of tart and sweet flavors guaranteed to tickled your buds. 129 Brighton Avenue, Allston, MA .
Gretta Luxe
Time was when Wellesley only meant straight and preppy. Well, no longer—thanks in no small part to this new boutique. Gretta Luxe carries an eclectic mix of international designers, from the clean, modern likes of Samsonite and Strenesse to more fashion-forward styles from Nanette Leopre and Ulla Johnson. There's a jeans bar stocked with denim from Earl Jean, Parasuco, C by Chloé, and Jean Paul Gaultier. And the shoe selection, including must-have models by Robert Clergerie, rivals any you'll find in the city. 94 Central St., Wellesley, MA grettastyle.com.
Regattabar
Jazz in its live form requires a venue that does it justice. With a slew of world-class acts ranging from timbale guru Eguie Castrillo to prog-funk trio Garage à Trois, this 220-seat space packs in the tables but leaves room for dancing out back. Bands play on the floor rather than a stage, making banter with the audience a common occurrence. 1 Bennett St., Cambridge, MA 2138, regattabarjazz.com.
The Secret Garden Pet Resort
Situated on 30 acres of lush green fields, this full-service grooming and boarding facility offers large private kennels for all of its four-legged guests, each of whom get a gated outdoor space and a deluxe doggie bed. If you’d like to treat your pampered pooch to a vacation as lavish as your own, upgrade to a luxury suite and take advantage of à la carte services such as nature walks, play sessions, and face time with Fido (via Web cam). 1040 Central St., East Bridgewater, MA 2333, secretgardenpetresort.com.
Sorellina
Dinner at Sorellina can cost as much as a flight to Italy, but at least here the life-altering food comes without jet lag. The hearty pappardelle with rabbit ragu is a bowl of Bologna, the delicate beet-filled ravioli further evidence to support the Italians' long-held claim that they taught the French everything they know about gastronomy. The only inauthentic items—and this is a good thing—are Shane Gray's desserts, which best their often disappointing Italian counter-parts: The impossibly light semifreddo is the finest we've ever had, here or abroad. One Huntington Ave., Boston, MA sorellinaboston.com.
People's Republik
An establishment must meet certain criteria before it can rightfully call itself a dive. It must be dark. It must be cheap. It must have spartan decor. Most critically, it must not attract tourists. By all these standards, the People's Republik earns the label. We love the surly waitstaff (expect a scowl if you waffle over an order) and the availability of both darts and hot dogs, which effectively cancel out the one potential dive-bar disqualifier: Ben Affleck is said to drink here sometimes when he's in town. 876 Massachusetts Ave., Cambridge, MA .
City Sports
We're all for supporting the little guys, but we have yet to find a neighborhood shop that can offer even half of City Sports' selection. With one swift stop, you can score the newest super-shock-absorbing running shoe, dart tips for your aging set, and CamelBak water packs for long hikes. Then there's the clothing for indoor and outdoor sports, equipment, and shoes to go with it. 480 Boylston St., Boston, MA citysports.com.
Big City Margarita, Sunset Cantina
This potent champion is a mix of Cuervo Gold, Cointreau, and Grand Marnier. Too potent? No problem. Try any of the other combinations at this sister saloon to the famous Sunset Grill & Tap, including the refreshingly tart Cantina Classic. With a choice of 65 tequilas and tangy flavors from lime to banana, the Sunset Cantina had the competition beat before you even walked in. 916 Commonwealth Ave., Boston, MA allstonsfinest.com/welcome.
The Rita Moreno, Gargoyles on the Square
A string of too many unfortunately flavored concoctions had put us off anything other than the classics...and then we met the Rita Moreno. A sexy southwestern cousin of the cosmo, it combines vodka, Rose's lime juice, and fresh lemon with sriracha and cilantro. The resulting creation strikes a perfect tart-sweet balance, then takes the experience to the next level with a spicy kick. 219 Elm St., Somerville, MA 2144, .
Yankee Lobster Company
The waterfront boasts flashy seafood emporiums mad with pricey cocktails and massive TVs, but we still head down the wharf to this retail arm of a decades-old lobster wholesaler. Sure, the napkins come in dispensers and the stellar view is of the street, but this is the freshest affordable seafood around. Grab a bowl of thick chowder, a basket of fried scallops, or go for lobster (in a bisque or on a roll) for a meal that's big on substance, not on flash. 300 Northern Ave., Boston, MA 2210, yankeelobstercompany.com.
Jerry Remy's
Owned by Mr. Red Sox Nation himself, Jerry Remy's has upped the ante (and the cholesterol count) for Fenway bars. The TVs are mammoth, and the kitchen serves a burger wedged between two pieces of fried dough. Best of all, the barroom is so close to the park that when the windows are open, you can even join a 'Yankees suck' chant while noshing on a tasty RemDawg sandwich. 1265 Boylston St., Boston, MA 2215, jerryremys.com.
Giblees
Occupying the better part of a nondescript strip mall on Route 114, Giblees has attire for every manly occasion: golf, work, weekends, and formal affairs—plus a pool table and coffee bar for gents who need a break from the dressing room. Assistance is available but never forced—our inquiry about a birthday bow tie for a super-stylish pal yielded a drawer full of dapper options. 85 Massachusetts 114, Danvers, MA 1923, giblees.com.