This beachfront resort is located just a short bike ride away from Edgartown. Not that you'll ever need to trek into town. The family-friendly property offers myriad accommodation options to suit everyone from couples to cousins, and has a bevy of amenities—tennis, yoga, pools—to keep the crew happy all day long. The Dunes, the Winnetu's restaurant, caters to a diverse crowd, including the kiddos. 31 Dunes Rd., Edgartown, MA 02539, winnetu.com.
Owner Philip Saul (pictured) will bring sartorially salty New England cred to your closet. Pick up a button-down, available in a variety of fabrics, from the store's eponymous label, made in Fall River. Or go for a trusty selection of familiar brands like Jack Purcell, Penfield, and Jack Spade—with surprising twists, like vintage leather brogues to pair with Unbranded Japanese selvage tapered denim jeans. Naturally, you'll want to grab some beer soap or beard oil on your way out. 577 Tremont St., Boston, MA 02118, saultne.com.
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.
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.
The 900-pound, umpteen-carat gorilla of the region's jewelry scene, Long's caters to North Shore treasure-hunters with 12,500-square-foot showrooms in Burlington and Peabody—and that's on top of five equally brilliant locations elsewhere in New England. With the 130-year-old company growing strong, customers reap the benefits in the form of a dazzling array of designer jewelry (John Hardy, Marco Bicego), rock-solid Swiss timepieces, and gifts that now include the famed Shreve gurgling cod. 35 Cross St., Peabody, MA 1960, longsjewelers.com.
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/.
Year after year, we find new winter gear we can't live without. So year after year, we revisit Ski Market. The store caters to everyone from bunny slopers to the black-diamond crowd with snowboards, snowshoes, and skis from A-list manufacturers like Salomon and Rossignol. It also carries sleek wear from the North Face, Burton, and Nordica that will keep enthusiasts looking cool—no matter how often or hard they fall. 860 Commonwealth Ave., Boston, MA 2213, skimarket.com.
Essentially a shrine to all things bath-related, Waterworks stocks handcut crystal sink accessories, refreshing grapefruit and ginger soaps, seductively quilted robes, and chrome faucet spouts so shiny you can see yourself in the reflection. With everything from cast-iron claw foot tubs to matte nickel toilet-paper holders, it's little wonder this temple of clean calls its tempting contents "jewelry for the bath." 103 Newbury St., Boston, MA .
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.
Aching for downward dog? Eager for a sun salutation? Stop by this frills-free Boylston Street studio. Yogi David Vendetti transforms himself from teacher to comedian to storyteller to motivator, all while delivering precise, clear instructions. His 90-minute classes cater to both beginners and advanced students. Every body leaves Back Bay Yoga in balance. 1112 Boylston St., Third Floor, Boston, MA backbayyoga.com/.
In a sea of nondescript restaurants catering to shoppers and office workers, Met Back Bay consistently impresses with its comfort-food-with-a-twist fare (think: rotisserie jerk chicken and head-on trout with shaved zucchini). Then there's the ham-and-cheese bar, where a multitude of potential pairings—prosciutto with Great Hill Blue, or hickory-smoked ham with Cabot clothbound cheddar?—support lingering at the bar with a glass of rosé. 279 Dartmouth St., Boston, MA 2116, metbackbay.com.
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.
Lighting makes a room, and the selection at Wolfers can give any home a welcoming glow. The Allston gallery has fixtures for every space—indoor and out. It caters to a variety of styles and budgets with fixtures including ornate chandeliers and funky kitchen pendants. The savvy salespeople can always shed light on any illumination problem, whether you need help changing a bulb or lighting an antique barn. 103 N. Beacon St., Allston, MA wolfers.com/.
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.
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.