Sargent Summer
A citywide celebration of the art of John Singer Sargent—at the Museum of Fine Arts, the Fogg Art Museum, the Isabella Stewart Gardner Museum, and the Boston Public Library—provides a rare chance to see the complete picture of this fascinating fin-de-siècle expatriate artists who considered Boston his American home.
Orchard
In the epicenter of Boston's skateboard scene, this Allston hangout takes things way beyond your typical shoes and decks purveyor. The profusion of brands (hats and tees from Somerville-bred Raw sit alongside national names like Nixon) is reason enough to make it your go-to, but Orchard also has cultural cred to spare: After taking a run or catching a demo on the store's mini ramp, pop upstairs to its Extension Gallery and check out works by local artists. 156 Harvard Ave., Allston, MA 2134, orchardshop.com.
Webster & Company
Boston's interior designers don't want you to know about Webster & Company: It's their secret trove of the classic American furnishings that picky New Englanders crave. David Webster and his son Peter have the area's exclusives on labels like Holly Hunt, Dakota Jackson, and Vaughan. One caveat: They only sell to the trade, so you'll need to hire an interior designer to get the goods. One Design Center Place-Suite 242, Boston, MA 2210, webstercompany.com.
Barbara Cole Lee + Company
As the longtime chair of the MFA museum school art sale, Boston's other Barbara Lee—the art consultant, not the gazillionaire—has built it into the largest event of its kind in the country. She brings that same passion to the needs of her high-powered customers, for whom she'll travel to the Venice Biennale and Art Forum Berlin in search of just the right piece. Lee is also an expert on the local scene, comfortable with both established stars such as Ellsworth Kelly and hotshots like George Rosa. 35 Fisher Ave., Brookline, MA 2445, barbaracolelee.com.
Shreve, Crump & Low
Boston's Breakfast at Tiffany's; press your nose to the glass and dream. This is the place to go with your honey when you want to browse without paying mind to price tags, to decide whether the bar-set or the channel-set band looks better with your solitaire. The staff gives everyone an upmarket education in ideal-cut diamonds. This is where you got schooled, and everyone respects the professor. 330 Boylston St., Boston, MA .
Beacon Hill Chocolates
As Boston's artisanal confectioners trend toward ever-weirder flavor combinations (poblano pepper truffles, bonbons oozing with olive oil), Beacon Hill Chocolates has us falling back in love with the classics: fillings like salted caramel and hazelnut praline delivered in beautifully tempered shells. The competition can just eat their quirky-candy hearts out. 92B Pinckney St., Boston, MA 2114, .
Mark Sardina
He's guided the East Boston Yankees and All-Stars to eighteen championships during the past eleven years with a humane style of managing that clearly pays off. Sardina founded the East Boston Athletic Association, coaches football in the off-season and T-ball (modified baseball for little kids) on weekends, and is a policeman, husband, and father of five (in his spare time). East Boston, MA
Menton
Barbara Lynch's haute-cuisine mecca was an instant sensation when it opened in 2010. The parade of tiny, striking dishes! The feather-light glassware! The prices! And the place has only improved over time, from the stunning prix-fixe menus to the staffers who anticipate your every need. We're not alone in noticing. In February the restaurant became Boston's first Relais & Châteaux property, a distinction reserved for the likes of Eleven Madison Park and the French Laundry. 354 Congress St., Boston, MA 2210, mentonboston.com.
Eco Centrix
Two floors of hair stylists, with better music and architecture than many Boston dance clubs. Ask for Mark or Steve, South Boston tough guys who'll talk to you about basketball, hockey, and baldness. Eco Centrix provides all the usual coffee, tea, and funny robes to change into, as well as some interesting people-watching: startling tattooed women with little round glasses alongside guys from Southie talking about the playoffs. 30 Newbury Street, Boston, MA .
Mottley's Comedy Club
Performing a set at a sweaty, cramped, underground club like Mottley's is the embodiment of what comics call paying your dues. Owned, operated, and booked by two funnymen (and their business partner), Mottley's is a proving ground for some of Boston's most promising comedy talent. The stage show is the main attraction, but if you hang back by the bar, you'll get a second serving of entertainment—eavesdropping on the performers' post-set repartee—for the same reasonable admission price ($8 to $20, depending on the show). Trinity Bar, 61 Chatham St., Boston, MA 2109, mottleyscomedy.com.
Commonweatlh Shakespeare Company
Even before Leonardo DiCaprio's Romeo and Gwyneth Paltrow's Shakespeare in Love, the Commonwealth Shakespeare Company's free outdoor performances showed Boston just how sexy the Bard can be. Under the brilliant direction of Steven Maler, the young, enthusiastic, multicultural cast of players brings Shakespeare to the Boston Common, using the recently renovated neoclassical Parkmand Bandstand—and all the world—as a stage.
Ed Pinckney
Former Boston Celtics player Ed Pinckney left the pros in the dust when he competed in a Boston Globe stock-picking contest. Pinckney tagged RJR Nabisco, which fell some 27 percent during 1994. But his competitors' picks fell even further. As any bench player knows, when the call comes you don't need to be great...just better.
EverybodyFights
Picture a boxing gym. If you're imagining a stark room with a ring and fluorescent lighting, you've clearly never been to EverybodyFights. George Foreman III's upscale boxing haven turns the stereotype on its head with boutique-inspired classes, spa-grade locker rooms, and a serious sound system. 15 Channel Center St., Boston, 857-250-4140; One Federal St., Boston, 857-990-3108; everybodyfights.com. 15 Channel Center St., Boston, MA 02210, everybodyfights.com.
Deep Thoughts
Walking Boston's increasingly sterile streets, you may find yourself occasionally wondering: "Where did our weirdness go?" Find out at Deep Thoughts, where expert oddmongers keep those crates teeming with obscure vinyl. For an extra dose of vitamin WTF, be sure to paw through the collection of far-out vintage sci-fi paperbacks. 138 B South St., Jamaica Plain, MA 02130, deepthoughtsjp.com.
Lana Barakat, December Thieves and Heist
This Middle East transplant's Italian jewelry and Japanese apparel have brought a global vibe to Beacon Hill. But the best part of a trip to December Thieves or Heist just may be Barakat herself, who's so darn fun to be around you might forget you're shopping at all. 88 Charles St., Boston, 617-982-6802; 51 Charles St., Boston, 857-239-9149; decemberthieves.com. 88 Charles St., Boston, MA 02114, decemberthieves.com.