20byNine
This little bar just off the main drag in Oak Bluffs has upped the cocktail game for the whole island with its expertly executed house-made syrups, infusions, and discerningly cultivated selection of boozes—including an imposing whiskey list. With classic Old Fashioneds and Sazeracs that meet or beat just about anything you can find in the city, the only clue that you’re on the Vineyard will be the sand in your hair. 16 Kennebec Ave., Oak Bluffs, MA 02557, 20bynine.com.
French + Italian
Even as her Boston outpost thrives, Aimee Lombardi continues to have faith in the suburbanite’s thirst for interesting fashion, traveling to Europe several times a year to bring home pieces that are thoughtful and thrilling but still hew to New England needs—chunky sweaters by Marni, memorable (yet wearable) dresses by Anne Willi. Insightful and cheery staffers remind shoppers why brick-and-mortar beats online: Chances are good you’ll walk out with something you never even thought to try on. 129 Washington St., Marblehead, MA 01945, frenchitalian.com.
Daleen Jordan, Trephin
Hair color has the ability to change the way the world perceives you. Daleen Jordan understands this, and doesn’t take her job lightly. Whether you’re hoping to transition from platinum back to natural brown or opting for a completely new look, be prepared to discuss the vision at length before any dye is applied. In fact, Jordan is so good at her job, you won’t need to reach for a hat as six weeks approaches: Her color remains lustrous even as the highlights and lowlights fade. 25 Temple Place, Boston, MA 02111, trephin.com.
S.H. Videography
This Back Bay videographer understands that there are certain moments you’ll want to relive over and over. Thanks to nearly three decades of documenting couples’ special days, S.H. Videography knows exactly what to linger on: the sweet first look; the vows that made the whole crowd cry; the heartfelt, two-Jamesons-deep toast from Uncle Don; the ring bearer breaking it down on the dance floor. As S.H. puts it, “A photo captures a moment in time, but a video captures time in motion.” 162 Newbury St., Boston, Massachusetts 02116, shvideography.com.
Five Spices House
Like the city’s options for Sichuan fare, this repeat winner just keeps getting better—and bigger. Last winter, the Chinatown original spawned a sibling kitchen in Central Square that instantly warmed the Scoville-loving hearts (and mouths) of Cantabrigians with its palate-igniting cauldron of “Scalding Fish Fillet” and thin-skinned dumplings drenched in beguiling hot sauce. (The puckery, vinegary stuff—like pork with pickled cabbage soup—is tempting, too.) Here’s hoping the fire continues to spread. 58 Beach St. , Boston, MA 5spiceshouse.com .
Ocean Edge Resort & Golf Club
Morning begins with coffee on the mansion's water-view terrace, a round of golf, or perhaps a massage at the brand-new spa. For the afternoon, it's standup paddleboarding along the private bay beach. Evening brings cranberry mojitos and painterly sunsets over the Brewster Flats at the recently opened beach bar. All of this without ever leaving your resort? If that doesn't sound like a blissful getaway close to home, we don't know what does. 2907 Main St., Brewster, MA 2631, oceanedge.com.
Kitchen Kibitz
Perhaps because it aligns with our modern taste for all things fermented, preserved, and pickled, Jewish cuisine is undergoing a much-needed renaissance in these parts. Playing a big role in its revival is this recurring pop-up from proprietor Jeff Gabel, who's managed to talk culinary luminaries like Bread & Salt Hospitality's Joshua Lewin into getting creative with everything from brisket-topped latkes to hamantaschen. kitchenkibitz.com.
Life Alive
A new Boston staffer—a meat-loving New York transplant—recently ran into the office, excited after "discovering" Life Alive. It was then that we realized how lucky we are to have had this organic café long before the whole grain-bowl-kombucha-juice-bar thing got trendy. Just try "The Adventurer," a mash-up of corn, beets, cruciferous veggies, cheddar, and sesame-ginger sauce over quinoa and rice and see for yourself. 765 Massachusetts Ave., Cambridge, MA 02139, lifealive.com.
The Catered Affair
Partnering with some of the area's most exclusive venues, this catering company turns out artfully plated fare that would be at home in the city's finest restaurants: chorizo beignets with romesco, espresso-roasted lamb sirloin. Maybe that's because executive chef Shane O'Neill, a L'Espalier alum, is the culinary genius behind the seasonally inspired menus. 70 Ledgewood Place, Rockland, MA 02370, thecateredaffair.com.
George Motta, Pino Bros Ink
You may recognize George Motta from an episode of Wahlburgers, during which he bestowed on Mark Wahlberg's friend Nacho a permanent portrait of Marky Mark himself. Even if you're after some decidedly subtler ink (and we hope you are), Motta's up for the task. Just be sure to book early, as the artist's reputation for crafting beautiful, incredibly realistic images has earned him a long waiting list for appointments. 1100 Cambridge St., Cambridge, MA 02139, pinobrosink.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.
Cielo
Authentic Mexican food? In Braintree? At long last, yes. Owners Roberto Leon and Guadalupe Fuentes lovingly plate real-deal Jaliscan dishes such as hearty torta ahogada (a spicy pork and bean sandwich) and a hauntingly complex enchiladas mole with chicken. The meandering river nearby adds to the charm, as does a tequila bar that stocks rare vintages. 1209 Washington St., Braintree, MA 02184, cielomx.com.
Fini Concierge
If there are more items on your to-do list than there are hours in a day—shopping for groceries, picking up prescriptions, scheduling appointments, waiting for the repairman—simply summon Fini Concierge. The company’s personal assistants on demand can even organize your home, take your car in for service, or string up lights for the holidays. No job is too small or too taxing. 665 Beacon St., Boston, 02215, finiconcierge.com.
Wequassett Resort and Golf Club
Based solely on the coolness of its bayside pool, Wequassett would swim away with this prize. But it also excels in every other way: The cozy cottage accommodations feel like the Cape of yore (albeit with Molton Brown toiletries and nightly turndown service); prime Signature rooms have fireplaces and unmatched water views. And then there's the exquisite golf course. The outdoor bar. The laid-back yet attentive staff. Need we go on? 2171 Head of the Bay Rd., Harwich, MA 2645, wequassett.com.
Hudson
You might say Hudson has New England roots and California tips. That's the product of the decor vision of owner-designer Jill Goldberg, whose store is an ecumenical palette of vintage, modern, romantic, and tribal. There are soft, sweet sofas by Shabby Chic; stately Oly chairs and ottomans; and art deco-accented lamps from Worlds Away. It's an aesthetic that can make any Boston home kinder, gentler, and full-on cozier. 312 Shawmut Ave., Boston, MA hudsonboston.com.