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.
Singh's Roti Shop
Drawing influences from Indian and Caribbean cuisines, this Trinidadian shop's roti wraps—pizza-size flatbreads griddled to order, then stuffed with meat (curried goat!), vegetables (sautéed cabbage, potato), and a house-made spicy pepper sauce (also available to go by the bottle)—are hearty and bold. Share one with a friend to leave room for the rest of the menu's treasures, which include curried chickpeas, garlicky puréed pumpkin, and spongy pholourie fritters with sweet-sour tamarind sauce. 692 Columbia Rd., Dorchester, MA 02125, singhsrotishop.net.
Brewer's Fork
Wood-fired pizzas and small plates make this cozy hang ideal for neighborhood types, but the curated draft-beer selection and splurge-worthy cellar stash upgrade it to a must-visit destination for suds seekers. An alum of the Publick House, co-owner Michael Cooney has built the relationships necessary to tap uncommon releases—from Allagash's cold-brew-infused Curieux to Almanac's dry-hopped sours—and stock the cellar with bottles of Orval for years to come. 7 Moulton St., Charlestown, MA 02129, brewersfork.com.
Stellabella Toys
So often, toy shopping is an experience in extremes: You’re either wading in aisle-to-aisle plastic packaging or browsing precious baubles curated to please parents’ aesthetics, not kids’. Stellabella, however, has found the sweet spot at its four Boston-area stores. Its stacking cups are environmentally friendly but also fun for your growing infant, and the baby dolls are soft, cuddly, and ethnically diverse. Also find German-made tricycles, sturdy play kitchens and firehouses, and Legos galore. 1360 Cambridge St., Cambridge; and other locations, stellabellatoys.com.
Desfina
You won't find modern, four-star Greek cuisine at this hole in the wall. But in an oddly delightful way, it reminds us of every humble neighborhood taverna we've savored in Greece, from the blue-and-white paper place mats to the scattered but amiable service. The tzatziki is a house specialty, the moussaka hearty and delicious, the ;horiatiki a true Greek salad—all plates so tasty, we'd be loath to smash a single one. 202 3rd St, Cambridge, MA 2141, desfina.com.
Sunset Grill & Tap
With 112 drafts and 380 total beers to choose from, this just ain't much of a competition. Sure, other places offer great lists: The Publick House has a slate of about 35 beers on tap. But 35 is not 112. And where Lord Hobo—another bar with an admirable lineup—can come off as aggressively hip, friendliness rules the day at this Allston spot. The servers enthusiastically steer you through the menu in search of a pint that'll suit your mood. And that mood, more often than not, is a good one. 130 Brighton Ave., Allston, MA 2134, allstonsfinest.com.
Chatham Bars Inn
Letting go of your inner Griswold in favor of a genuine vacation can be a challenge, but the Chatham Bars Inn makes taking it easy a breeze. The oceanfront resort serves R&R on a silver platter with a lengthy list of activities—croquet, kickboxing, nature hikes—along with pristine rooms, a top-notch destination spa, and no fewer than four Zagat-rated restaurants. 297 Shore Road, Chatham, MA 2633, chathambarsinn.com.
Manuel de Santaren and Carolina Tress-Balsbaugh of Manuel Santaren, Incorporated
These two designers are as ease working with chintz as they are with sleek, minimalist, and modern. That's largely because they have an eclectic clientele ranging from the Brahmin variety to dotcom whiz kids. No request is too obscure, and no historical period too difficult to recreate. In addition to transforming your abode into a house of style, de Santaren and Tress-Balsbaugh will micro-manage contractors and ensure the finished product is picture perfect, right down to the linens. 1 Designer Center Place, Boston, MA manueldesantaren.com.
Fabric Place
Don't throw that sofa out: Getting it re-upholstered couldn't be easier, thanks to Fabric Place. The array of chintz, cushions, bias piping, and floral repeats might be overwhelming—at last count there were more than 50,000 fabrics alone—but this is one store where the staff takes the time to show you around. On-call decorators will swing by your house for a consultation (free with a custom order of $299 or more), all jobs are carried out at the company's workrooms, and prices are extremely competitive. 136 Howard Street, Framingham, MA fabricplacebasement.com.
Eagle's Deli
When it comes to burgers, size matters. Test your gastrointestinal fortitude with Eagle's Deli's 'small' 1-pound Godzilla burger, topped with four slices of cheese and accompanied by a pound of fries, or the outrageous 3-pound Reilly burger, with a dozen slices of cheese and 5 pounds of fries. Each bite (and there are many) proves how good flavorful beef on a toasted bun can be. 1918 Beacon St., Brighton, MA 2135, .
Mike & Patty's
Tinier than many walk-in closets and closed by 2 p.m. each day, Mike & Patty's isn't your typical café. But it's home to the most satisfying handheld breakfast around—the "fancy" egg sandwich, a pile-up of bacon, cheddar, avocado, house-made mayo, and red onion on crisp multigrain bread. 12 Church St., Boston, MA 2116, mikeandpattys.com.
Young's Bicycle Shop
Call it the OG of Nantucket bike rentals: For nearly 100 years, this family-owned business has been operating just steps from the ferry terminal, marked by the trademark spinning bike wheel out front. And considering the wide selection of beach cruisers, mountain bikes, and mopeds on offer, it’s no surprise it’s been around so long. Need four wheels for your adventure? Check out the selection of over-sand vehicles for rent. 6 Broad St., Nantucket, MA 02554, youngsbicycleshop.com.
Faraway Nantucket
If, in fact, we go on vacation to lose ourselves, consider your new identity within the self-described quirky interiors of Faraway Nantucket. The hotel is comprised of six unique properties, each thoughtfully designed to reimagine the lives of historical former residents. Inside the main building on Centre Street lives the in-house restaurant and bar, complete with a gorgeous terrace and patio for savoring Nantucket’s fresh air. The vibe is coastal New England meets Alice in Wonderland, in the best way possible. 29 Centre St., Nantucket, MA 02554, farawayhotels.com/nantucket/location.
Sunita Bhandari Bhusal, The Threading Spa, Chestnut Hill
Celebs know that great eyebrows can dramatically improve a face. Thanks to Bhusal, we’re well versed in this phenomenon as well. "Something’s different!" ... "You look amazing" ... and our personal favorite, "Your brows are killer right now," were just a few of the flatteries flung our way after Bhusal worked her magic, first delicately threading and then gently tweezing until she achieved the perfect arch. Sensitive-skin types rejoice: Threading is cleaner than waxing, doesn’t leave any stickiness behind, and the chances of a burn are zilch. The Mall at Chestnut Hill, Newton, MA 2467, the-threadingspa.com.
Abe & Louie's
It's the oldest story in the book: Man tours steakhouses, steakhouses run gamut, man eliminates fading relics, lesser chains, and 'modern' meateries where the flourishes outshine the beef. And by the final page, Abe & Louie's and Grill 23 once again have emerged as the heroes of our tale. In terms of overall atmosphere, it's a draw (lively merriment versus relaxed elegance), but Abe & Louie's cuts are a touch more flavorful, the wine list a tad kinder to our bottom line, and the non-steak options—like the addictive crab cakes—a little nearer to perfection. After all, in a showdown this sizzling, victory is measured by degrees. 793 Boylston St., Boston, MA 2116, abeandlouies.com.