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.
The Wilbur Theatre
Big enough to command a prime Theater District spot but cozy enough to feel like an intimate club, the Wilbur has blossomed into Boston's premier place for biggish-name comedy. Recent headliners have included Amy Schumer, podcast pioneer Marc Maron, and Cosby antagonist Hannibal Buress, as well as Women in Comedy Festival sets by Glee deadpanner Jane Lynch and Cristela namesake Cristela Alonzo. 246 Tremont St., Boston, MA 02116, thewilbur.com.
Hive & Colony
Originally launched as a roving custom clothier in Manhattan (think: a food truck, but for made-to-measure menswear), Hive & Colony is now outfitting Boston's most fashionable grooms from its first brick-and-mortar, in Copley Place. The boutique, equipped with a measurement-capturing 3-D body scanner and a handsome bar, offers hundreds of fabric options for customizable suits and tuxes: Choose a lapel, add sharp buttons, and stitch your wedding date into the lining for a truly memorable getup. Copley Place, Boston, MA 02116, hiveandcolony.com.
Follain
Prepare to come in for a cleanser and leave with a changed life. Just one brief consult with a member of the dewy-skinned staff about the benefits of using natural products and you'll make plans to overhaul your bathroom cabinet. Luckily, it will take several visits to the Pinterest-worthy space to fill your shelves with serums, oils, and creams from Tammy Fender, True Botanicals, Osea, and May Lindstrom. 65 Charles St., Boston, 857-233-5211; 53 Dartmouth St., Boston, 857-284-7078; shopfollain.com. 65 Charles St., Boston, MA 02114, shopfollain.com.
Eugene Mirman
A Lexington native, Mirman made his name with appearances on Flight of the Conchords and a starring role in the animated series Bob's Burgers while living in New York. But he never forgot about his hometown, remaining a presence on Boston's standup scene and even creating a comedy festival here. He's since moved back to the area, letting us reclaim him as our own. eugenemirman.com.
Winston Flowers Design Studio
Sixty years in, there's nary a Boston venue that hasn't been decked with Winston's spectacularly traditional yet fresh-feeling arrangements. While the venerable chain's seven Great Boston stores do a brisk retail business, weddings are no small side project: Brides get close personal attention at the South End design studio. 160 Southampton St., Boston, winstonflowers.com.
River Gods
Central Square is one of Greater Boston's most eclectic neighborhoods, and no restaurant captures the area's unique vibe quite as well as River Gods. Small but not cramped, energetic without being earsplittingly loud, it's usually populated by a mix of students, yuppies, old-timers, and Che Guevara acolytes. On top of a great beer selection, there's a menu that should satisfy everyone from the pickiest vegans to the most carnivorous diners. 125 River St., Cambridge, MA 2139, rivergodsonline.com.
Clio
Among Boston's power-breakfast set, Ken Oringer's otherwise high-profile restaurant (and the chef's own 'baby') has mostly remained a close-kept secret. Exquisitely mannered servers glide through the elegant dining room, quick with the coffee and sparing with the interruptions. The only risk is that the caviar scrambled eggs, banana galettes, and fresh-baked zucchini bread might have you paying more attention to your plate than to your breakfast companion. 370 Commonwealth Ave., Boston, MA 2215, cliorestaurant.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 Chochituate Rd., Framingham, MA 1701, .
Aquascutum
There are certain advantages to Boston's lingering Anglophilia. Aquascutum is one of them. The sole American outpost of the venerable British chain carries trim tailored suits, broad-collared dress shirts, and vibrantly hued ties, as well as the clothier's signature line of elegant raincoats. The slickers are debonair enough to fit into even the dandiest wardrobe—and utterly inspirational here in our puddle-prone city. 450 Boylston St., Boston, MA aquascutum.co.uk.
Shreve, Crump & Low
Not for nothing has this Boston institution been a favorite among other Boston institutions (Isabella Stewart Gardner and Ted Williams, for starters) since it opened in 1796. The store is packed with sapphire rings and ruby and diamond necklaces that shine with all the quiet wattage of a chandelier. Want to cut back on the bling? Go for any of the elegant diamond-encrusted pearl pendants—heirlooms in the making, every last one. 330 Boylston St., Boston, MA shrevecrumpandlow.com.
Blades Board and Skate
What impressed us most about this place was that the friendly sales assistant had personally tried on 50 of the skates on display. Even better, she seemed genuinely interested in helping us find the right pair. The stock here also includes a smorgasbord of gear, such as helmets, pads, and socks. The staff arms you with tips on finding a qualified instructor and Boston's places to skate, so you'll leave feeling ready to roll. 349A Newbury St., Boston, MA blades.com.
Barbara Krakow
Known far and wide as Boston's "mini MoMA," the Krakow is Ground Zero for emerging contemporary art. The gallery's owners consistently go out of their way to dig up new artists, adding a strong dose of local talent to the mix, and rounding it out with international masters. Look for as much photography (documentaries from Nicholas Nixon, for example) as painting and sculpture (a recent series of Cameron Shaw's work blew us away). 10 Newbury St., Boston, MA barbarakrakowgallery.com.
Addo Novo
It's easy to get swept up in interior trends, but when you're looking for edge (that won't later cut you), Addo Novo offers the midcentury's greatest hits, along with contemporary interpretations. What's so brilliant about the Barcelona couch or the George Nelson Bubble Lamp, you ask? These thoughtfully designed pieces are perfectly scaled for Boston's smaller, European-style living spaces. 1313 Washington St., Boston, MA addonovo.com.