Regattabar
Jazz in its live form requires a venue that does it justice. With a slew of world-class acts ranging from timbale guru Eguie Castrillo to prog-funk trio Garage à Trois, this 220-seat space packs in the tables but leaves room for dancing out back. Bands play on the floor rather than a stage, making banter with the audience a common occurrence. 1 Bennett St., Cambridge, MA 2138, regattabarjazz.com.
The Beachcomber
Cape Cod isn't exactly famous for its surfing, but the Beachcomber on Cahoon Hollow Beach is the quintessential surfers' hangout, with battered boards on the walls, sand on the wood floors, and an annual visit from surf god Dick Dale. Early on, the joint is full of families grabbing dinner, but once the sun goes down, a younger crowd moves in for strong mixed drinks and beer. 1120 Cahoon Hollow Road, Wellfleet, MA 2667, thebeachcomber.com.
Avalon
Big venues usually mean small performers—not in terms of musical stature, but because you're so far away the act looks like a dot with a guitar. So thank God and Pat Lyons for Avalon, where despite its capacity of 1,950, you never feel far from the stage. A spacious main floor, tiered stairs, and a balcony with great stage views make seeing big-time indie performers—Rhett Miller and Doves—seem almost intimate. 15 Lansdowne St., Boston, MA .
Vics Boathouse at Victoria Station
Serene by day, sultry by night, and boasting tantalizing harbor views, Vic's hosts an endless cavalcade of events (open-mike nights, karaoke, and dancing), fueled by an expansive beer list—Pretty Things, Alchemist, and Saison Dupont, to name a few—and a creative cocktail menu. To cool down after heating up the dance floor, go for a refreshing Aperol Cucumber Fizz, sipped slowly on the patio or dock. 86 Wharf St., Salem, MA 1970, victoriasstationsalem.com.
Offshore Ale Company
Oak Bluffs is the antithesis of the Jersey Shore, so why do most of its bar options seem so well suited for "gym, tan, laundry"? Escape to the Offshore Ale Company for its rotating selection of unique house-made brews, like the Flying Monkey, a Belgian-style ale aged in chardonnay barrels. The kind of bar that allows—nay, encourages—patrons to toss peanut shells onto the floor, it's sure to become your favorite stomping ground. 30 Kennebec Ave., Oak Bluffs, MA 2557, offshoreale.com.
Uptown Espresso
It's not hard to miss Uptown Espresso, tucked into the first floor of a townhouse in the South End—although once you know it's there, it's virtually impossible to walk past. The coffee, a dark roast from upstate New York, is bracing without being overwhelming; tea lovers can choose from more than 20 blends. Order an iced espresso, latte, or steamer to go, or settle in for a quiet moment on the sunny glassed-in porch. 563 Columbus Ave., Boston, MA .
Bloomingdales
The heart of the capacious first floor at the new multimillion-dollar Bloomingdale's in Chestnut Hill is its smartly laid-out, wholly welcoming cosmetics department. Hard-to-find brands include Clé de Peau and Trish McEvoy; personable, informed, and refreshingly nonpushy salespeople make for zero-pressure lingering; and real-world lighting means it's no shock when your $23 cobalt blue Dior mascara turns out to be very blue, indeed. The Mall at Chestnut Hill, Chestnut Hill, MA 2467, bloomingdales.com.
Barneys New York
Just as toppings make the sundae, accessories make the outfit. Barneys boasts a broader inventory than most, with two floors of jewelry, scarves, gloves, glasses, and other add-ons from 200-plus brands. Upstairs, Barneys Co-Op has charms by Bing Bang and funky shades by Dita; downstairs, you'll find haute Goyard totes and Balenciaga wallets. All in all, it makes for a feast for the style-famished. 100 Huntington Ave., Boston, MA 2116, barneys.com.
C.O. Bigelow
Cracked elbows, oily T-zones, and damaged locks all require different care routines, which is why C.O. Bigelow fills its floor-to-ceiling shelves with enough creams, soaps, balms, masks, and bath salts to satisfy even the biggest product pack rat. Favorites include Kevyn Aucoin makeup, Frederic Fekkai hair care, and exclusive skin-care treatments from Patricia Wexler M.D., as well as the store's eponymous line of quince and grapefruit hand and body lotions. Copley Place, Boston, MA 2116, bigelowchemists.com.
Bambini Design
If children are the future, surely their rooms shouldn't be stuck in the past. Shop Bambini for color-saturated contemporary furnishings and gadgets such as Kaloo stuffed animals and floor mats, Vibel modular play sets, must-have Bugaboo strollers, and Sozu lighting to illuminate your bright young things. Because it's never too early to learn to appreciate good taste. 82 Boylston St. (Rte. 9), Brookline, MA 2445, bellabambinidesign.com.
Louis Boston
Louis's unparalleled offering of women's designs by fashion darlings including Marni, Tuleh, and Zac Posen—not to mention a formidable men's collection with everything from Brioni to Trovata—makes it a legendary local house of style. The revitalized first floor now includes more bath products, linens, and vintage home goods than ever, and the salespeople remain polite, not pushy. 234 Berkeley St., Boston, MA louisboston.com.
Italian Design
Outshining the competition is serious business at Italian Design, where high-wattage style emanates from futuristic floor lamps, funky ceiling fixtures, and warm, colorful bedside sconces. Everything on display is a modern work of art. Don't fret if you're unfamiliar with lighting science; the knowledgeable staff can help you with projects of all sizes. 82 Boylston St., Brookline, MA italian-design.net.
Underground Snowboards
Truth be told, the hard-core boarders who staff the sales floor here would probably prefer to spend their days carving up the slopes, though you'd never know it from the attentive and well-informed service they provide. All the top brands are available, and the store offers package deals tailored to a range of skill levels and budgets. 860 Commonwealth Ave., Brookline, MA .
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 .
Brookline Booksmith
Brookline Booksmith is dedicated to the art of browsing. This cozy store allows book lovers to curl up on the wood floor and thumb through their favorite tomes. Friendly staffers are eager to make suggestions—unlike the aloof or harried help you find in some of the superchains. Booksmith's Writer and Readers series brings the community face-to-face with authors, who've included Grace Paley, Alice Hoffman, and other literary luminaries. The store also encourages bibliophiles to get their noses out of their books and support local charities. 279 Harvard St., Brookline, MA .