Looking for the feel of a Vineyard family estate without the squabbles over taxes and when to sell? Welcome to the Winnetu. Built in grand New England style, with summertime clambakes, easy access to South Beach, and a brand-new pool and hot tub, this family-friendly destination is the perfect place to make memories year after year. Whether you curl up in front of the fire in one of the resort’s sprawling two-bedroom cottages or uncork a chilled bottle of pinot grigio in a kitchenette-equipped studio, you’ll feel right at home. 31 Dunes Rd., Edgartown, MA 02539, winnetu.com.
Every well-shod woman has the closet to prove it—sensible pumps for work, streamlined flats for weekends, sky-high Christian Louboutins just because—and chances are, there's a Barneys shoebox on her shelves. The department store's cavernous shoe salon proffers the red-soled attention getters, of course, but also more-unique and unexpected styles—caged Alaïa sandals, sinewy canvas heels from Walter Steiger, paint-splattered Maison Martin Margiela low-tops, studded cowboy boots by Isabel Marant—always keeping you one step ahead of the fashionable masses. Copley Place, Boston, MA barneys.com.
Local masterpiece-mongers tend to deal in one of two extremes: jejune still-lifes geared to designers who spruce up Back Bay sunrooms, or sprawling esoterica that cause poseurs to start lusting for home-display space. Hewing a noble path between pear paintings and "environments," Lanoue focuses on established artists who tackle traditional genres—portraits, landscapes, even floral studies—with modern flair. Though varied in style, the monthly exhibitions all balance craftsmanship with conceptual edge, requiring neither advanced degree nor audio tour to blow you away. 125 Newbury St., Boston, MA 2116, lanouefineart.com.
New from New York, the McEvoy line offers hip, practical palettes for lips, eyes, and cheeks, and even has a zippered filofax-style case that you can fill with customized inserts (for all those important little daily appointments to powder your nose). The trained crew at Neiman's invites you to try before you buy. Educating rather than arm-twisting, patiently demonstrating special techniques like "push and wiggle" so you can line your lids like the pros—even after you get home—they do one side of your face, then it's your turn. Neiman Marcus, 5 Copley Place, Boston, MA .
Few things are more intimate than hiring someone to clean your home. Tremendous Maid, thankfully, is all business: Fill out an Internet request form with your square footage and home layout, and you'll quickly hear back about scheduling options. The actual cleaning was both impressive and a bit guilt-inducing, as the team scrubbed items we willfully ignore: baseboards, toaster oven, mini blinds. By the time they were done, our house was as pristine as the day it was built. 270 Centre St., Jamaica Plain, MA tremendousmaid.com.
Spend at least one evening of your Vineyard getaway at this cozy island favorite known for unpretentious, locally sourced dishes, but be sure to reserve in advance. The place is beloved by locals and presidents alike (Barack Obama is a regular on his vacations; his White House decorator designed the space). Return for brunch the next morning and take an extra order of made-from-scratch Limpopo doughnuts home with you. State Road is open for much of the winter, too, when you can enjoy fun off-season specials in front of a roaring fireplace. 688 State Rd., West Tisbury, MA 02568, stateroadrestaurant.com.
One of the last survivors of Kenmore Square’s sterilizing overhaul, Nuggets gets you back in touch with old weird Boston and encourages you to bring that history home. Since 1978, obsessed musicologists have explored its wide range of rock, R & B, folk, jazz, and classical box sets, then dug through shelves of books and other tuneful memorabilia. If you’re looking for an old 12-inch dance single or an LP by a long-neglected local band like Heretix or the Real Kids, check out the racks in front and keep an eye on the store’s Facebook updates. 486 Commonwealth Ave., Boston, MA nuggetsrecords.com.
Step one (sufficiently difficult): Coordinate 15 schedules to pick a date for your birthday/ anniversary/coming-out party. Step two (near impossible): Find a place that will seat everyone. The private dining room at Eastern Standard—a plush, chandeliered alcove off the main dining area—will accommodate parties of up to 18 with ease. The waiter assigned solely to your group means you won't ever feel neglected; the fully enclosed space means you won't have to struggle to hear what your pals are discussing at the other end of the table. Hotel Commonwealth, 528 Commonwealth Ave., Boston, MA easternstandardboston.com.
Tess Enright knows what she likes—and, more to the point, what she does not. The sartorial littérateur has no interest in words like "trendy" or "hip," instead preferring ones like "seasonless," "ageless," and "assured." Her stores are filled with pieces she thinks every woman should own, in understated colors that purposefully override fad: Piazza Sempione cashmere coats, Prada ballet flats, Jil Sander suiting. Three locations include a new Newbury Street outpost, but Tess herself sticks close to Newton, where she's been doling out straightforward advice since 1999. 1241 Centre St., Newton Center, MA 2459, tessandcarlos.com.
There's a myth that says running requires nothing more than comfortable sneakers and willpower. Untrue: If you're serious about the sport (or are merely trying to look as if you are), you're also going to need some sweat-wicking shorts and shirts, a cardiac monitor, several pairs of cushy socks, a hat and/or sunglasses, maybe a windbreaker, and, oh yeah, one of those belts that holds little water bottles. Marathon Sports has all the gear you need, and some you probably don't. And its running-obsessed staff is clued in and honest enough to help you sort out which is which. 671 Boylston St., Brookline, MA 2445, marathonsports.com.
Generally speaking, a person's favorite dive bar is the one closest to home. The Model is that rare specimen—a neighborhood bar that's gained destination status for drinkers from all over the city. Everything inside this 75-year-old Allston joint screams classic dive: loud tunes, a pool table, $2 Pabst Blue Ribbons on tap, $4 Bushmills on the rocks, a crowd that ranges from hip to drip, and urinals barely clean enough to, well, urinate in. Mediocre fare (this is a dive bar, after all) is served til 10. 7 North Beacon St., Allston, MA .
It's easy to forget, in our world of PDAs and ADD, that drawn-out dining can be a thing of delight. Everything at this hotel restaurant, from its jacket-and-tie requirement and exacting service down to its immaculate china and crystal settings, speaks to a serious attention to detail. The Gallic-inspired menu spotlights delicacies such as Long Island duck breast with melon-basil salad, beef tenderloin with pea purée, and iced Key lime soufflé. And at the end of your leisurely meal, should you find yourself too stuffed to drive home, you can wend your way upstairs for a stay in one of Blantyre's opulent suites. 16 Blantyre Rd., Lenox, MA 1240, .
Dainty eaters, beware. Only those with a hankering for a little grease and gobs of pork-addled flavor are able to handle the made-to-order plates at Cambridge's stick-to-your-ribs haven. Sure, the chicken's great, but there's also smoked turkey with collard greens, and bread crumb-encrusted mac and cheese, and silky sweet potatoes, and (the only thing harder than settling on an order here, you'll find, is nabbing one of the few seats). Coast Café may not have much competition in these parts—KFC? Popeyes?—but it could surely hold its own in Dixie. 233 River St., Cambridge, MA 2139, .
Gigantic sandwich? Or gigantic cookie? Such are the tough choices at Something Natural, an out-of-the-way eatery with a fiercely loyal following. Meals can be brown-bagged for the beach or enjoyed at one of the picnic tables that dot the lawn, and lunch orders like Sheila's Favorite (mayo, Swiss, carrots, pickles, and tomatoes on home-baked oatmeal bread) and turkey salad with Granny Smith apples and raisins on wheat provide a solid base for what regulars know is a flawless chocolate chip. (Actually, now that we think about it, it's not a tough call after all: Obviously, you get the gigantic sandwich and the gigantic cookie.) 50 Cliff Road, Nantucket, MA 2554, somethingnatural.com.
Most municipal courses have recovered nicely from the dastardly winter of 2002—particularly Franklin Park, which is in great shape this year—but George Wright is still something special. Established in 1938 and designed by the legendary Donald Ross, it boasts stone walkways, tight fairways, and divine holes such as the par-4 tenth, a dogleg left with a green nestled in a wooded dale. The nastier holes will shut up that annoying buddy with the 3-handicap who claims public courses are "too easy." 420 West St., Hyde Park, MA cityofboston.gov/golf/GWGC/.