Overflowing pints of Bass and Guinness, live entertainment including Karaoke Tuesdays, the obligatory logo-embroidered polos for sal—smack in the center of Chatham, the often rowdy Squire is the quintessential Cape pub. Weekend nights host a medley of thirsty characters; stick around long enough, and you've got good odds of witnessing unlikely, though not altogether uncommon, end-of-the-evening trysts between local anglers and summering society types. 487 Main St., Chatham, MA 2633, .
Bostonians are only the Bourne Bridge away from a summertime escape to the Cape. But when you want to feel transported to more-tropical climes, travel to the tiki-bar-style setup at Shore Leave in the South End. It's the perfect place for cooling off with fruity yet finessed rum-soaked drinks and Pacific Rim–inspired snacks such as okonomiyaki tater tots swimming in jalapeño cheese with katsu sauce and bonito. 11 William E Mullins Way, Boston, MA 02118, shoreleaveboston.com.
Based solely on the coolness of its bayside pool, Wequassett would swim away with this prize. But it also excels in every other way: The cozy cottage accommodations feel like the Cape of yore (albeit with Molton Brown toiletries and nightly turndown service); prime Signature rooms have fireplaces and unmatched water views. And then there's the exquisite golf course. The outdoor bar. The laid-back yet attentive staff. Need we go on? 2171 Head of the Bay Rd., Harwich, MA 2645, wequassett.com.
Surprise—not everyone on Cape Cod covets pressed khakis and leather loafers. Step out of conservative Falmouth and into Maxwell & Co. to find cutting-edge American and European looks by Strenesse, Etro, and Twilltwentytwo. Teens and grandmothers alike are sure to find something appropriate in this large space, which also carries clothes by Lacoste, Ted Baker, and Robert Graham. 200 Main St., Falmouth, MA shop.maxwellandco.com/.
The Cape has its share of pubs ready to get you good and sloshed, but if you'd rather savor a drink than slam it back, the Nor' East Beer Garden, in Provincetown, is an excellent choice. The tiny, shirelike oasis has an extensive list of craft beers, and its selection of inventive, garden-infused cocktails (consider an arugula mojito or a "rhubarbarita") offer some peaceful refreshment amid the antics of Commercial Street. 206 Commercial St., Provincetown, MA noreastbeergarden.com.
Seven thousand yards of championship golfing, nestled in 170 acres of sweet-smelling pine forest: The 72-par Dennis Pines is a course to be reckoned with. With water at four of the holes, enough trees to test anyone's accuracy, and the notorious par-5 twelfth, the course is arguably the toughest—and certainly one of the most beautiful—on Cape Cod. Amenities are plentiful, including an expansive driving range and practice green, a nice little lounge, and a well-stocked pro shop. Rte. 134, East Dennis, MA dennisgolf.com/.
Owner Philip Saul knows that casual doesn’t have to mean sloppy. To wit: Where else can you try on Japanese selvedge denim in two contemporary, tailored fits? Whether you’re shopping for cheerful printed tees and canvas shorts for your next Cape vacation or fitted button-downs and slim-fit pants for breezy weekends in the city, playing it cool never looked this sharp. 577 Tremont St., Boston, MA 02118, saultne.com.
In the past year alone, Pollen Floral Design owner Krissy Price has dreamed up masterpieces for a distillery engagement party, a restaurant wedding, and seaside nuptials on the Cape. She’s as comfortable working in jewel tones as she is in pastels, giving big, beautiful blooms the starring role in every custom installation, free-flowing bouquet, and color-packed centerpiece she crafts. MA bostonpollen.com.
Most Cape restaurants fall into one of two categories: beachy seafood shacks staffed by teenagers, or precious tourist traps with huge markups. The Naked Oyster is neither—just a sleek raw bar and restaurant featuring oysters fresh from chef Florence Lowell’s farm. Enjoy baked bivalves of every variety, inventive fish preparations, and a civilized bar scene fueled by well-made drinks. 410 Main St., Hyannis, MA 02601, nakedoyster.com.
Every beachside community needs a restaurant with a view, a meeting place of sorts where families and friends can gather for birthday celebrations or just to gaze and graze on a sunny afternoon. For the mid-Cape, that place is the Pelham House. After a recent major refresh, a heated roof deck offers unobstructed Nantucket Sound views all around, not to mention a killer menu featuring plenty of fresh seafood. As for the apré-dinner scene? Multiple fire pits surrounding the sea-level dining area are perfect for cocktails and moonlit ocean views. 14 Sea St., Dennis Port, MA 02639, pelhamhouseresort.com.
A good breakfast joint is the kind of place where you can settle down with your morning paper, sipping from a bottomless cup of self-serve coffee, and order what mom used to cook (or what you wish she had). After seven years in Ball Square, SoundBites is still sans frills; just good home cookin' fresh out of the oven and off the grill. Order French toast or waffles with fruit and you'll get a mound of cool, glistening slices of sunshine atop the warm, light battercakes. The other side of the menu proves there's more than one right way to do eggs, whether they're Moroccan, Benedict, or an omelet. 708 Broadway, Ball Square, Somerville, MA .
Even overcast days at Chatham Bars Inn feel sunny. First, there's the setting: a graceful, 1914 building overlooking the Atlantic, surrounded by quiet, individually decorated (and kitsch-free) cottages. Second, there are the activities: croquet, tennis, biking, rides in the property's antique cars, or, for kids, shoreline critter hunts, pirate visits, and karaoke. The nightly candelit dinners of local seafood at the water's edge are almost absurdly romantic. Few properties on Cape Cod manage to balance kid-friendliness with that kind of genuine excellence. This one does—even when it rains. 297 Shore Rd., Chatham, MA chathambarsinn.com/.
When this hypnotically arty restaurant-bar designed and owned by a local architect made its debut four years ago, it not only lent zing to the South Shore dining scene, but also beckoned Cape-bound cosmopolites with its expertly shaken martinis, mod leather furnishings, and moody firelight. The arrival of new executive chef George Willette last fall boosted the culinary substance—e.g., tuna tataki, lobster and goat cheese pizza—to match Ember's abundant style, making this nightspot a white-hot proposition, indeed. 459 Plain St. (Rte. 139), Marshfield, MA 2050, .
Muses nonwithstanding, the Art Store sells everything your magnum opus needs, and at prices that won't leave the artist in you starving. Forget rummaging through piles of 200 pre-stretched canvases to find the size you want; it's all neatly ordered against the wall. Every shade of paint—oil, acrylic, watercolor, you name it—is represented, and the paper selection runs from handmade, violet-embedded sheets to plain foam core. Like to sit while you sketch? There's furniture here too, plus easels and mesh file boxes. Come to think of it, the large, open, and neatly arranged space may just inspire you after all—to organize your studio. 401 Park Dr., Boston, MA .
Though we Bostonians are awash in seafood, there's shockingly little variety among those serving it to us. There are the clam shacks (Morse Fish Company, No Name), the executive favorites (Legal, Turner, Skipjack's, et. al), and the amusement parks (Barking Crab, Kingfish Hall). Only two restaurants truly cater to foodies—the South End's B&G Oysters and the North End's Neptune Oyster—and we love 'em both. This year Neptune can credit its edge over B&G to a slightly less formal vibe (shared tables, dishtowel napkins) that feels right for the times. That, and the fact that we spent the winter polishing off glorious scallops, ceviche, and cioppino here, and left happy every time. 63 Salem St., Boston, MA 2113, neptuneoyster.com.