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.
Sacco's Bowl Haven
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, .
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 .
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.
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.
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.
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.
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.
December Thieves
When Lana Barakat decided to rethink her two Beacon Hill clothing-and-gift boutiques, she envisioned one store catering to home décor and another specializing in apparel and accessories. This divide-and-conquer strategy created more room for something Boston has been sorely lacking: high-end women’s footwear. Handcrafted by European and American designers, Barakat’s collection includes everything from metallic leather boots with an offset heel to cheetah-print loafers to sneakers with a velvet knot tie—perfect for navigating the cobblestones in style as you stroll up Charles to check out what other treasures await at the December Thieves home store. 51 Charles St., Boston, MA decemberthieves.com.
Louis Boston
Buyer Debi Greenberg scours the globe to find the in fashion for men and women alike. Her Back Bay store is known the world over for its incredible timing, with many design darlings of the fashion press finding their way onto its floors before they hit the big time. The store caters to a wide variety of ages, from street fashion on the ground floor to power suits on the second and third levels, and a mix of women's wear designers from Kiton to Imitation of Christ. There's also an extensive and cutting-edge makeup counter, Salon Mario Russo, and a top-notch restaurant. 234 Berkeley St., Boston, MA louisboston.com.
The Maids Home Services
We aren't ones to cry over spilt milk, as our floors can attest; our couch has more hair on it than our cat. Without a speck of judgment, the Maids clean up our act month after month, dusting baseboards, degriming showers, and all but eliminating any traces of pet (except for, of course, the pet itself). They're quick, well priced, and unobtrusive: Aside from the preternatural sparkle and neatly triangled toilet paper, you'd never know they'd been there. 179 Boylston St., Jamaica Plain, MA 2130, .
The Port Hunter
On an island, it’s not surprising that bars cater to either locals or tourists, rarely both. The beauty of this lively spot is that those distinctions don’t apply — everyone’s welcome. There’s indoor and outdoor seating. The craft cocktail program is inventive without being pretentious. And the food, like Vineyard flounder tacos and hickory-grilled whole fish, is far superior to most pub grub. But what will really draw you in is the sound of laughter and live music bouncing off the exposed red-brick walls and out onto Main Street. 55 Main St., Edgartown, MA 02539, theporthunter.com.
BHLDN
Rallying the troops for a shopping sesh isn’t so easy when your ’maids live in different places. Thankfully, BHLDN’s virtual styling appointments make cross-country celebrating a breeze, ensuring each gal can successfully browse and shop online. As for the dresses? Catering to a range of sizes, styles, and budgets, BHLDN’s selection of gowns in a rainbow of easy-to-match hues — accessible via the shop’s new swatch program — all but ensures your girls will be wearing their picks long after your special day. 220 Boylston St., Chestnut Hill, MA 02467, bhldn.com.