The Beach Plum Inn
There’s no shortage of charming inns everywhere on the Vineyard, but none of them has the vantage point of this rustic farmhouse overlooking the absurdly picturesque fishing village of Menemsha. With rooms and cottages available, it embodies the laid-back up-island vibe; the path to the beach, for instance, winds past the chicken coop. Umbrellas, beach towels, and chairs are complimentary, and guests get coveted passes to Lucy Vincent and Squibnocket beaches, but the real reason to stay here is the mind-bending sunsets over Menemsha Bight. 50 Beach Plum Ln., Menemsha, MA 02535, beachpluminn.com.
Thom Solo
Once upon a time, you could only snag Thom Solo’s cutting-edge heels and boots by placing a custom order. Recently, though, the designer has found a way to scale production of his coveted footwear, making it more accessible to all. But that doesn’t mean he’s compromised on style or quality: Solo continues to revolutionize shoe design with innovative pairs like his iconic ruffle pumps and sexy croc long boots. thomsolo.com.
Barlette
The team behind the always-booked-up Brookline hit restaurant Cobble has done it again, this time with a BYOB cocktail bar. You read that right: You bring the booze, and Barlette provides the mixers, glassware, snacks, and dramatic-floral-wallcovering-bedecked vibes, complete with a variety of themed nooks to explore, like the book-filled Library. Just be quick — reservations open at noon on the first of every month and go fast. 318 Harvard St. #11, Brookline, MA 02446, drinkatbarlette.com.
Sacco's Bowl Haven
Once you hear the candlepins crashing, smell the freshly made clay-oven pizza, and taste the beer — lots and lots of locally made beer — you’ll understand why people flock from all over to score a lane at Sacco’s. In fact, try making a reservation, and you might be shocked at just how popular the Davis Square holdover has become. Luckily, several lanes are available on a first-come basis — so show up early and stay late. 45 Day St., Somerville, MA 02144, americanflatbread.com/locations/somerville-ma.
Omori Izakaya
Looking for quick after-work bites of teriyaki-glazed chicken skewers, crispy chicken karaage, or fried octopus nuggets, perhaps washed down with a crisp Sapporo beer? Or maybe a longer, lingering dinner of rich bone-broth ramen or prettily plated donburi rice bowls? Omori is a shining example of the Japanese-style pub known as an izakaya, a casual genre perfect for a night out with friends. Brookline and Malden, omori.net.
White Elephant
Maybe it’s the waterfront vistas that make White Elephant resort, situated on the east side of Nantucket’s downtown harbor, so magical. Maybe it’s the specialty bed linens, so beloved by guests that you can actually buy them, mattress included. Maybe it’s the pool, where on sunny afternoons you can sprawl out on a plush cushioned lounge chair or in a private cabana and sip a berry smoothie from the snack bar. Or in fact, maybe it’s all these things at once that make a stay here as blissful as an island breeze. 50 Easton St., Nantucket, MA 02554, whiteelephantnantucket.com.
Kimball Farm
Kimball Farm started as an ice cream stand on a sandy patch of parking lot, a rite of passage for local kids to eat cones as big as their heads. Today, the Westford location has socially distanced family fun down to a science with attractions that rival most theme parks. Here you’ll find well-monitored lines for gargantuan sundaes; an al fresco snack shack with kid-friendly meals (cheesy tater tots, hot dogs) and local beer for grownups; live music; and even mini golf, bumper boats, and batting cages for open-air fun with your pod. 400 Littleton Rd. (Rt. 110), Westford, MA 01886, kimballfarm.com.
Valentino
Unlike the fable told about bridesmaids' gowns, a piece from Valentino can actually be worn again, and not just to another black-tie event. The current line of classic silhouettes and punchy colors is on-trend without being trendy, so the garments won't quickly look dated. The designs can also be taken from night to day with toned-down accessories and a more-casual shoe, so that printed crՎpe de Chine dress that made you feel like Cinderella at the fundraising gala doesn't need a glass slipper to stun again. 47 Newbury St., Boston, MA 02116, valentino.com.
Patrice Vinci, Patrice Vinci Salon
Patrice Vinci is the beauty fairy godmother you never knew you needed. With an old-school Boston accent and gorgeous golden tresses of her own, the colorist wields her brushes like magic wands and her dyes like potions. Case in point: a visit that turned our thick blond curls a rich, multi-toned copper that looked so incredibly natural, even our mother swore we must have entered this world a redhead. Expert or enchantress—why can't it be both?—Vinci will help your hair live happily ever after. 91 Newbury St., Boston, MA 02116, patricevinci.com.
The Blue Bunny
Once in a blue moon, you get a Blue Bunny. Cofounded by children's author-illustrator Peter H. Reynolds (The Dot, The North Star) five years ago, the magical little bookshop has grown into an area hub of reading and imagination. In scarcely more than 1,000 square feet it offers classic kids' books, young-adult novels (some for grownups, too), and lots of low-tech, high-fun games. But more than that, it provides a genuine springboard for creativity. There's always an art or writing workshop planned, and this spring the store launched a magazine created by and for youngsters called The Hutch—underscoring how rare this Bunny truly is. 577 High St., Dedham, MA 2026, .
Out of Town News
Big-city newsstands have mostly gone the way of afternoon dailies, but there are a couple of exceptions. Out of Town News gets the nod this year for four reasons. First, it's bigger than fellow standard-setter Copley Square News, and the extra real estate means it offers even more newspapers and magazines from all over the world. Second, it's a national historic landmark, meaning it's in little danger of disappearing. Third, it's right in Harvard Square, where the people-watching is first rate. And last, because Nini's Corner, directly across Massachusetts Avenue, is a pretty good newsstand itself—a boon to anyone too lazy to cross the street to find a magazine. Zero Harvard Square, Cambridge, MA .
Uncle Pete's
A welcome addition to gifty, girly Beacon Hill, this new boutique is as hip as it is friendly. On any given day, you'll find Uncle Pete's proprietor Peter Tam chatting about everything from dark denim to indie music. His fashionable menswear lines include Rag & Bone, Tretorn, Cloak & Dagger, and Surface to Air, and he's eager to chime in with helpful, practical advice on what goes with what. Bonus: A women's section means your lady friend can look as cool as you, sir. (Buy her something nice, why don't you?) 119 Charles St., Boston, MA 2114, .
Dorfman Jewelers
Sitting on a block somewhere between Juicy Couture and Newbury MedSpa, Dorfman's looks a tad out of place among its campier neighbors. Chalk it up to the stately facade and, no doubt, to the fact that this store practically oozes staying power. For two generations the Dorfman family has dealt exclusively in European-cut diamonds and other gems; these days they also sell such illustrious names as Harry Winston, Van Cleef & Arpels, and Breguet. Perhaps most representative is the in-house Barbara Collection, open-link gold pieces inspired by the clan matriarch that are at once unpretentious and enduring—much like the venerable Dorfman itself. 24 Newbury St., Boston, MA 2116, .
Broadway Bicycle School
"If you want something done right, do it yourself" is a nifty aphorism, but it's also true that we could all use a little help sometimes. The versatile grease monkeys at this bike co-op offer options for all levels of hands-on experience. Stand-and-tool rental runs $9 per hour, an unflappable mechanic to talk you through your repair costs $18 per hour, and if you just can't be bothered, they'll tune your ride to perfection at reasonable rates. If you really want to get your fingernails dirty, the school offers classes in repair and wheel building. 351 Broadway, Cambridge, MA broadwaybicycleschool.com.
Boston Sports Club
You might want to join this club for the parking alone. Where else can you pay $1 during peak hours for an indoor spot? New owners have done a complete rehab on the old Allston-Brighton Squash Club, which now pulls its weight with the other big-name clubs in town. To wit: acres of cardio machines, including the hot new elliptical walkers; brand new Cybex; free weights of every description; six squash courts; a huge aerobics studio (that doubles as a gym); and a dedicated spinning room with enough colored lights on the ceiling for a Broadway show. 15 Gorham St., Boston, MA .