Harbor View Hotel and Resort
You could camp out on the wraparound porch and have an amazing time at the Harbor View, what with the postcard view of the Edgartown lighthouse. But thankfully, they've got the goods inside, too: boutique-style rooms with balconies, a private marina with a fleet of charter boats, a heated pool, kids' programs, and Henry's, one of the best bars on the Vineyard. 131 N. Water St., Edgartown, MA 2539, harbor-view.com.
Straight Wharf Restaurant
The Straight Wharf remains one of Nantucket's toughest reservations. Perhaps guests know that the celebrity contingent (regulars include Brian Williams) might be on hand. But we're guessing it has more to do with the food—standouts like halibut chowder sprinkled with house-made bacon, and a clam bake featuring lobster and chorizo over corn and littlenecks. 6 Harbor Sq., Nantucket, MA 2554, straightwharfrestaurant.com.
Hingham
It's actually two markets in one: On Wednesdays you'll find goods by the town clock in Hingham Square, while on Saturdays the vendors set up shop at Hingham Bathing Beach. Either way, South Shore denizens stream in for the colorful array of produce, meats, and seafood from stands like Weir River Farm, Great Cape Bakery, River Rock Farm, and more. Saturdays May through November, 10 a.m.-2 p.m. at Hingham Bathing Beach; Wednesdays June through October, 11 a.m.-3 p.m. in Hingham Square, Hingham, MA hinghamfarmersmarket.org.
The Grog
Temple to haute cuisine and artisanal cocktails it's not. But if what you crave is a frosty IPA, good-humored barkeeps, and feisty locals who aren't afraid to rock an open mike, there's no better spot to toss one back than the Grog. Weekends bring live music from reggae to blues, and occasional events with craft brewers keep beer geeks satiated. 13 Middle St., Newburyport, MA 1950, thegrog.com.
The Tannery
Most men suffer bad relationships with their shoes. They scuff, give off smells (not the men, the shoes), and need frequent tying. And the guys we know hate to shop to replace theirs. So a one-stop shoe store is a godsend, and the Tannery is worth a pilgrimage. From Tevas to Timberland, sandals to the most softly shining leather loafers, the Tannery can shoe a foot for any occasion, and in any of an enviable range of labels. 402 Boylston St., Boston, MA thetannery.com.
Bonpoint
When the nanny complains that little Madison has outgrown her pinafores, get yourself (or send your personal assistant) to Bonpoint. The French clothier's exclusive pastel sweaters, jumpers, pants, and dresses are acclaimed by fashion editors and parents alike for their high quality and adorable designs. This cuteness costs, though—upwards of $100 for simple overalls, $230 for silk dresses, and $280 for cashmere baby one-pieces. Baby Gap, it isn't. 18 Arlington St., Boston, MA bonpoint.com.
Isis Parenting
Yes, we know the cultlike following can be a turnoff. But no other store has a more-comprehensive selection of products or better-educated employees, eager to help locate the ideal solution for your particular nursing/sleeping/strolling/fill-in-the-blank dilemma. Even if you don't enroll in one of the informative prenatal classes or organized playgroups, you'll still walk out feeling like an empowered mom or dad. Prudential Center, Boston, MA isisparenting.com.
City Sports
Whatever your passion—volleyball, basketball, yoga, even bocce—City Sports has the gear you need, including high-performance pieces from its in-house CS line. Ask one of the sporty employees to help you browse the Gore-Tex jackets, or find cleats or sneakers that'll let you hit the field, court, or track running. 480 Boylston St., Boston, MA 2116, citysports.com.
Barneys New York
Your credit card may get a workout here, but think of the time you'll save: an entire wardrobe in one fell swipe. Workdays are covered with Surface to Air button-downs and Alexander McQueen ties; for weekend wear, scoop up hoodies and tees from T by Alexander Wang. And if your pockets start to feel empty, there's always the selection of wallets and handkerchiefs to fill 'em back up. 100 Huntington Ave., Boston, MA 2116, barneys.com.
Intimacy
When it comes to underthings, there are places for function (Macy's, Lord & Taylor) and places for fashion (Agent Provocateur). But Copley Place's Intimacy is both kinds of shops in one. Flattering, well-priced, practical lingerie and bra-fit swimwear (the biggest selection in town) suit a variety of occasions and cup sizes, while red-hot lace pieces by Aubade and Simone Pérle and a rainbow of Hanky Pankys are just for fun. 100 Huntington Ave., Boston, MA 2116, myintimacy.com.
Louis Boston
With its efforts this past year focused on footwear, Louis Boston now rivals national department stores in quantity—and beats them outright in quality. Delicious flats by Devotte and Gryson line one wall, while heels both timeless (Mayle) and risk-taking (Proenza Schouler) perch along another. And although $800 Balenciagas remain part of the offerings, it's possible to score an equally dynamite pair of Coclico sandals for a few hundred bucks (as, unable to resist, we did). 60 Northern Ave., Boston, MA 2110, louisboston.com.
Twisted Village
When they are not playing in the local band Major Stars, Wayne Rogers and Kate Biggar offer the city's most impressive collection of rare, avant-garde, and alternative music. In one aisle, collectors can find seminal releases by The Fall and Rain Parade; in another, lunar jazz from the likes of Sun Ra and Ornette Coleman. In addition to an extensive selection of European psychedelic rock, the Village also stocks local music, reggae and world beat, and new vinyl from emerging independent labels. 12B Eliot Street, Cambridge, MA .
Essentia
See you later, Pottery Barn: Essentia is the perfect place to find a hostess, shower, or birthday gift. Accessories from this boutique have that handmade quality without smacking of hokey, homespun earnestness. Instead, the wares are stylish. On offer are one-of-a-kind pottery pieces from the UK, Europe, and local areas, an array of linens and cushions, and a smattering of handmade jewelry pieces and other fashion accessories, including handbags and silk-printed scarves from RISD. The Mall at Chestnut Hill, Chestnut Hill, MA essentialifestyle.com.
The Cambridge Artists' Cooperative
A mix of traditional crafts, whimsy, and fine arts endows the Cambridge Artists' Cooperative with unusual charms. On a magical mystery tour of its three floors, you'll find everything from blown-glass hummingbird feeders to pine-needle baskets to wearable art, with prices from $7 to $2,000. And you'll understand why craftspeople themselves voted the store one of the Top Ten Retailers of American Craft. 59A Church St., Cambridge, MA .
Belmont Wheelworks
Cycling enthusiasts from across the country— including three-time winner Greg La-Mond— pedal to Wheelworks for its competitive prices and great service. Customization doesn't get better than this: Three-time Olympian John Allis, a partner in the store, helps fit you to a bike or builds you one from scratch. You can even test ride the large selection on a nearby off-road course. Around the corner, Wheelworks Too offers closeouts, older models, and used bicycles at lower prices. 480 Trapelo Rd., Belmont, MA .