The Beach Plum Inn
Secreted in the hills of Menemsha overlooking Vineyard Sound, the Beach Plum—and its satellite cottages and houses—is a cozy little sanctum that epitomizes the absolute best parts of the Vineyard in the summer. It offers tennis courts, bike rentals, kayaks, and passes to exclusive Lucy Vincent Beach, but also low-key perks like being able to gather eggs from the inn’s chickens in the morning. Throw in one of the finest restaurants on the island, and you have a recipe for the ideal under-the-radar getaway. 50 Beach Plum Ln., Menemsha, MA 02535, beachpluminn.com.
Blackbird Doughnuts
Blackbird has a big new nest—a massive Brighton production facility/storefront to supply its growing flock of doughnut shops—but thankfully, the expansion hasn’t compromised the quality of its fresh-daily delights. We still get wide-eyed when we spot the baker’s simple yet luscious vanilla-glazed variety, as well as more-inventive iterations amped up with cold-brew coffee, sprinkled with chili-lime salt, or laden with tart cranberries. 100 Holton St., Bay #4, Brighton, MA blackbirddoughnuts.com.
Dani Wagener, DW Beauty
Ever wonder how celebrities achieve that flawless red-carpet glow? It's all about the airbrush—makeup, that is. Boston beauty expert Dani Wagener, who's worked with Jenny McCarthy and Emily Deschanel, specializes in this technique. Armed with false eyelashes and the perfect lip color, she'll arrive at your prep site and promptly get about the business of making you look like a star. 326 A St., Boston, MA 02210, daniwagenerbeauty.com.
The Sinclair
With a cozy, intimate vibe and a who's-who of trendy touring acts (upcoming headliners include Sonic Youth legend Thurston Moore), the Sinclair has in short order made itself the hippest place in town for a show. Expanded offerings have included emo night, as well as the occasional offbeat comedy show or Point Break Live! experience. 52 Church St., Cambridge, MA 02138, sinclaircambridge.com.
Renae Connolly, Benedetto
Renae Connolly's desserts are such exquisite works of refinement and balance, we've come to think of her as a real-life Sugar Plum Fairy. Whether you indulge in a wedge of classic torta al limon jazzed up with a bright-pink prickly-pear gel stencil on the plate, or a rustic elderflower granita elegantly surrounded by a sugar lace toile, its sweetness cut with tart poached rhubarb and bright basil meringue, the finale to your Italian feast will be on point. One Bennett St., Cambridge, MA 02138, benedettocambridge.com.
The New School of Music
In one room, you might find tots trying to vocally or physically interpret instrumental sounds as part of the school's popular Dalcroze Eurhythmics program; in another, grade schoolers might be exploring the cultural roots of playground songs. Once they're hooked, sign them up for group or private lessons on instruments ranging from the piano to the didgeridoo. 25 Lowell St., Cambridge, MA 02138, newschoolofmusic.org.
Pini Swissa
Pini Swissa identified our hair dilemma immediately—lose the bulk around the crown that grows in bushy after a week, he advised. This is the man who styles Tom Brady, after all, so he should know. A close fade on the side nicely transitioned into a fuller top that looks great when styled with a bit of product, or parted and slicked for formal occasions. No one mistook us for Mr. Ba¼ndchen afterward, but we did receive a few long glances while strolling down Newbury Street. 18 Newbury St., Boston, MA 02116, piniswissa.com.
Todd Maul, Cafe Artscience
Imagine a boozy amuse-bouche of scotch, inhaled as a plume of smoke. Or a mai tai that actually grows stronger thanks to rum-soaked banana leaves lining the walls of your tiki glass. Armed with gadgets like a centrifuge and Le Whaf, an invention that turns liquids into vapors, Todd Maul has created a cocktail program that’s as much kitchen chemistry as it is adult playground. 650 E. Kendall St., Cambridge, MA 02142, cafeartscience.com.
Ventuno’s Back Bar
The al fresco bar tucked behind Ventuno is less polished than the anchoring Italian restaurant, but that’s part of the charm. With a beachy-casual vibe owing to a cover of vines and an ever-so-random crowd that could, on any given night, include Patriots owner Robert Kraft, pop star Meghan Trainor, one-time frat boys, and a crew of local fishermen, it’s the rare local’s hangout that’s welcoming to outsiders. Bonus points for an unbeatable selection of craft beer. 21 Federal St., Nantucket, MA 02554, ventunorestaurant.com.
Noel McKinnon, Makeup 2 Die 4
Brides call Noel McKinnon the "wedding whisperer," a nod to her cucumber-cool poise. Armed with a silky southern accent, individual lashes, and airbrush foundation, she creates flawless looks in a soothing atmosphere—which makes sense considering she's worked with everyone from Miss Universe Olivia Culpo to comedian Amy Poehler. makeup2die4.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 .
E6 Apothecary
Makeup maniacs need go no further than E6. The store has most of the buzz-worthy lines in stock, including Shu Uemura, Molton Brown, Tarte, Watosa, Biotherm, and Three Custom Color Specialists. What's more, the intimate, refreshingly low-pressure atmosphere allows you to sample the products without being attacked by overzealous salespeople—a welcome alternative to more traditional makeup counters. 167 Newbury St., Boston, 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.
Newbury Comics
Great variety (imports, independents, jazz, classical, rock, soundtracks) isn't enough. Low prices (new discs as low as $9.99) aren't enough. Even a knowledgeable, friendly, and helpful staff isn't enough. Because every devotee of Newbury Comics knows that, on top of all of the above, it's the store's own distinct culture—a loud, high-energy setting in which you never quite know whom you're going to meet—that makes it more than the sum of its parts. Harvard Square, 36 JFK St., Cambridge, MA newburycomics.com.
Bukowski Tavern
A great pub is measured not only by its pints, but also by the quality of the food it offers to absorb all that booze. Bukowksi's, for its part, offers plenty of delicious ways to fortify yourself for the myriad varieties of stellar frosty brews it pours. The burgers are large and messy, just as they should be. And the array of "barfly food"—the White-Trash Cheese Dip, a rib-sticking plate of barbecued chicken tenders—is sure to sate late-night appetites. 50 Dalton St., Boston, MA .