Ocean Edge Resort & Golf Club
At a resort, it's easy to get lost in the shuffle. But not here, where a personal concierge caters to your whims. That's a welcome addition to the Ocean Edge, which has undergone $50 million in renovations to its villas, mansion rooms, and restaurants. So now you get the coddling you'd expect from a boutique hotel, plus smart touches like a fridge stocked with ice cream and all the fixin's for s'mores if you book a villa. 2907 Main St., Brewster, MA oceanedge.com.
Martin's Restaurant
Regulars know to get to Martin's before noon, as this bustling brunch spot, with its no-frills menu and attitude-free staff, always fills up fast. Guests doodle with crayons on paper place mats—the best are hung on the bulletin boards—as they wait for custom omelets with homemade hash browns or French toast topped with fresh fruit. And just so lazy latecomers don't miss out, the restaurant serves brunch until 3 p.m. 49 Railroad St., Great Barrington, MA martinsgreatbarrington.com.
Giblees
Giblees may not look like much from vantage of Route 114, but behind its inconspicuous storefront is an international array of the finest men's suits and casualwear this side of I-95. Lucky, Paper Denim & Cloth, Hugo Boss, and Coogi are just a few of the big-city brands you'll find at this surprisingly swank suburban haberdashery, whose cordial staff has 50 years of experience making the men of the North Shore look their best. 85 Andover St. (Rte. 114), Danvers, MA giblees.com.
The Pet Cabaret
Catering to the "thoughtful pet owner" this colorful store functions more like a community hub for animals and their devoted humans than a place to buy supplies. It wouldn’t be unusual to pop in for treats, toys, or food—all of which skew heavily natural—or to wash a dirty pup in the self-serve tubs, and end up chatting with fellow customers about a nontoxic cure for hot spots, a topic that only other pet owners will gladly discuss. 4404 Washington St., Roslindale, MA 02131, thepetcabaret.com.
Hotel Commonwealth
Courtesy of Hotel Commonwealth With floor-to-ceiling windows and a string-lit terrace showcasing Green Monster vistas, Hotel Commonwealth’s new event space hits it out of the park. Part of the hotel’s recent $50 million makeover, the just-built wing is now the perfect spot for both Sox fans and culinary-minded couples to celebrate their love: The catering menu features dishes inspired by on-site hot spots Eastern Standard and Island Creek Oyster Bar. 500 Commonwealth Ave., Boston, MA hotelcommonwealth.com.
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.
The Bite
If the location in Menemsha's western cove feels a bit desolate, rest assured: The Bite's bright blue picnic tables will beckon like a desert oasis. You'll quickly find yourself tearing through brown paper bags turned translucent with grease to get at overflowing cartons of oysters, clams, zucchini, and shrimp delicately fried to a flavorful crisp. Grab a cup of the creamy quahog chowder to complete what might be the quintessential summer meal. 29 Basin Rd., Chilmark, MA 2535, thebitemenemsha.com.
Helmand
The Helmand This off-the-beaten path spot in East Cambridge has been around for decades, yet somehow manages to make us feel like we're discovering something new every time we visit. Such are the wonders of the authentic Afghani cuisine—kaddo, or pan-fried baby pumpkin baked with ground beef, and aushak, or paper-thin ravioli skins with a bright leek filling. Don't pass up dessert—the homemade cardamom ice cream with pistachios is a knockout. 143 First St., Cambridge, MA helmandrestaurant.com.
Wine Galley
Wine stores tend to cater to either experts or idiots. If, like most of us, you're somewhere in between, head to the Wine Gallery, a shop as welcoming to neophytes as it is to Robert Parker wannabes. The knowledgeable staff will happily guide you to a hard-to-find amarone or the best 10-buck malbec. And if you still can't decide, try before you buy at the store's 'wine jukebox,' which dispenses free half-ounce samples of 32 reds and 16 whites. 375 Boylston St. (Rte. 9), Brookline, MA 02445-6007, wine-gallery.com.
Little Stevie's
Miss your adolescence? The Formica booths at Little Stevie's aren't just seats, they're time machines that sweep you right back to braces, babysitting money, and after-school specials. And the pizza's right there with you: pillowy, bubbly, and doughy edges with a paper-thin and oven-charred crust, sweet and tangy tomato sauce, and a hot, dense layer of mozzarella. Say what you will about teen angst; pie this good makes it all seem worthwhile. 1114 Boylston St., Boston, MA littlestevespizzeria.com.
Crane & Co. Papermaker
Dalton-based Crane's 100 percent cotton paper has been used exclusively to make U.S. currency since 1879. And while your wedding invitations may be slightly less official than that, they're no less important—and should be no less grand. Crane's seasoned staff sees to it that your stock and print quality are the finest possible, and that you've got everything covered, from save-the-date cards to envelope linings and thank-you notes. Prudential Center, 800 Boylston St., Boston, MA crane.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, .
Picture Perfect Pets
More kindergarten teacher than drill sergeant, Bette Yip can teach pooches to do anything—sit; stay; scoop their own poop (we can dream, can't we?). If Rover can't make group classes—or hasn't yet learned to play well with others—sign him up in advance for private lessons. After a few one-on-one sessions with Yip, he'll be ready to fetch the paper and roll over like a pro. 9C Dudley Street Pl., Arlington, MA 2476, betteyip.com.
Linens on the Hill
The essentials for a good night’s sleep don’t change with the trends. Since 1987, this Beacon Hill store has been catering to our restful needs with high-thread-count bedding from established brands like Yves Delorme and Sferra, plush robes from Laurence Tavernier, and silk pajamas from PJ Harlow. And to make your waking hours a little dreamier, it also stocks a selection of scented soaps and soft Egyptian-cotton towels. 52 Charles St., Boston, MA 02114, linensonthehill.com.
Pastoral
Fort Point Italian restaurant Pastoral gets points for a prime location (blocks from the Boston Children's Museum) and an excellent parking situation (get a $5 validation for the nearby Farnsworth Garage). There's ample stroller parking in the takeout area, and tables are widely spaced so antsy children can roam free. The kids' menu, meanwhile, offers thoughtful touches like gluten-free pizza; paper and crayons arrive while you wait. 345 Congress St., Boston, MA 02210, pastoralfortpoint.com.