Tres Gatos
The brunch at this record shop/tapas bar caters to savory seekers—and hangover chasers. Here the "put an egg on it" philosophy reigns supreme, evidenced by dinner-menu staples like the lamb bocadillo, which gets the morning-after huevos treatment come brunch. While you're waiting for your table (there will be a wait), browse the back bookshop for fiction, art books, vinyl, and a broad collection of food magazines that will surely whet your appetite. 470 Centre St., Jamaica Plain, MA 02130, tresgatosjp.com.
Lynwood Café
When it comes to bar pizza on the South Shore, there are important standards to meet. Are the to-go pies placed between two cardboard plates and slid into a brown paper bag? Is the crust hand-pinched in the pan to give it the perfect crunch? Is the joint cash only? And, most important: Do the locals love it? Lynwood checks all the boxes. For bar pizza the way it’s meant to be experienced, commit to the house special, which comes loaded with baked beans (trust us), onions, and salami. 320 Center St., Randolph, MA 2368, lynwoodcafe.com.
White Elephant Village
The sister property to the iconic White Elephant harborfront hotel, this luxe resort caters to guests’ every whim: Need a ride to dinner? A loaner bike to explore the island? Scoops of ice cream to keep the kids entertained at the pool? Done, done, and done. The circa-2012 inn offers plush rooms and suites, but for a picture-perfect—and stress-free—family getaway, you’ll want to reserve one of the spacious " premier residences," which offer one-, two-, and three-bedroom configurations. 19 N. Water St., Nantucket, MA 2584, whiteelephantvillage.com.
Dorfman Jewelers
Yes, there's loads of ice on hand here, in the form of Patek Philippe timepieces and Henry Dunay necklaces, but the warm and patient service at Dorfman will thaw any notion that buying big-time bling is a daunting endeavor. In business for seven decades and counting, the family-owned jeweler caters to both Beacon Hill bluebloods and a younger, funkier clientele with diamonds and pearls aplenty, vintage-inspired house lines, and New England's only Van Cleef & Arpels salon. 24 Newbury St., Boston, MA 2116, .
Bob Slate Stationer
Old souls who still prefer old-fashioned card stock to Evites may get carried away when shuffling through the pens, pencils, and paper of every possible type at Bob Slate. For an extra-personal touch, you can work with the store's knowledgeable and creative staff to custom design your own full set of embossed, 100-percent cotton stationery, a move that will have you leaving your calling card all around the city. 1288 Massachusetts Ave., Cambridge, MA 2138, bobslate.com.
The Haberdash Vintage
When Amy Chase's online selection of '60s-era boots, sequin tops, fur-trimmed coats, and accessories grew too big for Etsy, Chase found herself trolling for vintage trailers. Now she stations her Bellwood camper at outdoor markets, festivals, and parking lots, and books private shopping parties with her movable boutique, the Haberdash Vintage. 138 Green St., Worcester, MA 1604, haberdashvintage.com.
Royal Jewelers
Chances are the jewelry you saw on the pages of a national fashion magazine is under the glass at Royals. Penny Preville, Kisselstein-Cord, SeidenGang, Doris Panos, TechnoMarine, and Philippe Chariol are just some of the designers represented at this family-run business, which has catered to the North Shore area for 50 years. Look for a store face-lift this fall that will add an in-house David Yurman boutique. 58 Main Street, Andover, MA royaljewelers.com/.
Panificio
Warm sun streams into this Charles Street bakery-cum-café's expansive windows, where the clientele kicks back (sometimes for hours) over high-octane lattes, crumbly slices of walnut bread, and the daily papers. And while you can clearly witness the hustle and bustle outside, it fades as you sink deeper into the shop's meditative momentum. 144 Charles St., Boston, MA panificioboston.com/.
Mr. Sid
Head west, young man, to Newton Centre. There you'll find Mr. Sid, the shop that caters to classy guys looking to dress to the nines in Armani, Hugo Boss, Zegna, and Corneliani. Helpful, knowledgeable, and courteous salesmen escort customers through the store, which is divided into smaller areas by collections. Tired of shopping? There's an in-store pool table, a hair salon, and a well-stocked bar. 1211 Centre St., Newton Centre, MA mrsid.com/.
Gatsbys
Don't be fooled by the faded shabby-chic exterior: Beyond the white wicker sidewalk furniture is a shop stylish enough for any city's streets. Buyer Pamela Fink stocks Gatsbys with premium products including Paper, Denim & Cloth and True Religion denim; Theory tops and trousers; and a rainbow of Petit Bateau T-shirts. There's also a selection of sporty shoes, Cosabella lingerie, Kiehl's products, and Juicy Couture loungewear. 25 Railroad St., Great Barrington, MA .
Bakers' Best
Although it has expanded its dining area, we love Bakers' Best most for its sophisticated takeout options. Everything comes with detailed reheating directions that will fool your guests into thinking you cooked it yourself. But don't worry: The employees here won't give away your secret. They'll even come over to cater for you. 27 Lincoln St., Newton Highlands, MA .
Sacco's Bowl Haven
Photograph by Bob O'Connor There are flashier lanes in town—theme park-like emporiums with flat-screen TVs and signature cocktails. But the laid-back atmosphere of Sacco's wins it top honors. It's complete throwback awesomeness, from the candlepin setup to the pencil-and-paper mode of scorekeeping. If there's a wait, grab a seat at the bar, order a Flatbread Company pizza and a Pretty Things pint, and kick back. 45 Day St., Somerville, MA 2144, .
Peking Tom's Longtang Lounge
It may sound tacky on paper, but in person, Peking Tom's is deliciously campy and cool. With colorfully ironic splashes of Asian pop culture, delightful retro tinges, and plenty of room for lounging, this hidden Downtown Crossing destination with its highly competent service is perfect for parties of 2, 12, or 20. The menu relies on a perfect balance of sweet and sour, fried and juicy, meaty and delicate. Just remember—don't overload on kumquat mojitos before digging into the crispy sweet-chili squid or orange and tamarind-glazed spareribs. 25 Kingston St., Boston, MA .
Loyal Supply Co.
JARED KUZIA Husband-and-wife team Ryan and Kimberly Habbyshaw take the term “locally made” seriously: Watch as the paper enthusiasts bring their witty, colorful greeting cards to life on a 1911 printing press at the center of their Pinterest-worthy Union Square shop. Of course, if you just need to pop in for a few delightfully analog everyday accoutrements—Autopoint pencils, Appointed notebooks—they stock those, too. 21 Union Sq., Somerville, MA loyalsupplyco.com.
Barneys New York
While these days any clothing boutique worth its counter-side Hanky Panky display boasts a 'denim wall,' none can touch the selection at the downtown Barneys. The racks and tables and shelves of jeans include the blue-chip (True Religion, Paper Denim & Cloth), the hard-to-find (Acne, Edun), and the affordable (J Brand, Cheap Monday). Bargain hunters salivate over the store's semi-annual sale, which recently saw a pair of $300 Ksubis go for less than $60. 100 Huntington Ave., Boston, MA 2116, barneys.com.