The Beacon Room
Vacationers can play it two ways as they settle into this welcoming, wood-filled space for a midday meal: fuel up for an afternoon of high-impact romping in the sand, or just plain fill up for several hours of indolence under the sun. For the former, there's leaner fare such as grilled chicken on Portuguese muffins and a salad with gorgonzola, walnut, and sun-dried cranberries. For the latter, choose from plus-size portions of clam chowder, crab cakes, fish and chips, and other Cape Cod classics—and enjoy the wistful glances from those sticking to moderation (poor things). 23 West Road, Orleans, MA 2653, beaconroom.com.
Sundae School
Cape Cod sometimes feels as though it's sinking under the weight of its many ice cream shops, but Sundae School rises above with handmade, creamy flavors in such addictive permutations as espresso crunch, Kahlúa chip, and Bass River mud (coffee ice cream with fudge, almonds, and chocolate chunks). Add such toppings as fresh, plump blueberries, bananas, buttery hot fudge, homemade cream, and a fresh Bing cherry, and you've got more than just an ice cream treat. You've got a religious experience. 606 Main St. (Rte. 28), Harwichport, MA sundaeschool.com.
Land Ho
Want a side of local color with your Devil's Purse pint? Pay a visit to this neighborhood hang, where Cape Cod memorabilia—from family crests to vanity plates—fills every inch of wall and ceiling space. It's not all about the kitsch, though: Bartenders behind the lacquered wooden bar aim to please, and the late-night menu satisfies with grub for both landlubbers (burgers) and seafarers (fish and chips). 38 Main St., Orleans, 508-255-5165; 429 Main St., Harwich Port, 508-430-0404; land-ho.com. 38 Main St., Orleans, MA 2653, land-ho.com.
Wequassett Resort and Golf Club
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.
Maxwell & Co.
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/.
Nor' East Beer Garden
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.
Dennis Pines Golf Course
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/.
Sault New England
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.
Pollen Floral Design
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.
The Naked Oyster
Courtesy Photo 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.
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 Chatham Squire
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, .
Hingham Farmer's Market
Start your Saturday with a snack from the Great Cape Baking Company—we suggest the apple-cider doughnut or a hunk of rosemary bread. Load up on local seafood from C&C Lobster & Fish (based in nearby Hull) and fresh produce from Mary Bukujian's Hanson farm. Enjoy the view of Bathing Beach. Drive home happy. Hingham, MA 2043, hinghamfarmersmarket.org.
Main Street in Essex
Why limit yourself to one seafood venue when you can have it all on just one block? Main Street's dream team of major seafood players—Tom Shea's (for unbeatable grilled seafood), Woodman's (for topnotch classic fried clams, lobster tails, and scallops), and Periwinkles (for expertimental, fusion-minded fish dishes)—offers Cape Ann's highest concentration of fine fish. Put together, they provide what may just be the perfect seafood sampler. Main Street, Essex, MA .
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.