Pelham House Resort
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.
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.
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.
The Naked Oyster
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.
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.
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.
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.
Blue Willow Fine Foods and Bakery
Save the formal service and immaculate silverware for your power lunches in the city. On the Cape, you want to grab something fast and friendly—and then head right back outside. At Blue Willow, the ingredients are fresh, the sandwiches inventive, and the baked goods all made from scratch. Our superlative midday meal: the signature grilled chicken and Brie panini followed by a fudgy, walnut-studded 'outrageous' brownie. 1426 Route 6, Wellfleet, MA 2663, .
Arnold's Lobster & Clam Bar
The long lines don't lie: Arnold's serves fried clams at their messy best alongside the fluffiest, tastiest onion rings we've ever eaten. The location doesn't hurt either: It's right on the Cape Cod Rail Trail, with picnic tables in the shade of tall pines where you can pitch your kickstand and enjoy surprisingly reasonably priced seafood on a cafeteria-style tray. As a gesture to gourmets, there's even a raw bar. But stick to the specialties: fried clams, steamers, lobster, and corn on the cob. Rte. 6, Eastham, MA arnoldsrestaurant.com.
Cottage Street Bakery
This tiny bakery makes breads, sandwiches, and European-style pastries worth searching out—plus unbelievable muffins, pies, and wedding cakes. But what puts it over the top is its inelegant-sounding "dirt bomb," a dense, indulgent breakfast pasty dusted with cinnamon and sugar. It's a sweet way to jump-start any Cape Cod morning. 5 Cottage St., Orleans, MA cottagestreetbakery.com.
Singing Beach
This half-mile stretch cuts a sandy swath into the rocky terrain of Cape Ann's coastline, giving picnickers plenty of sheltered space to spread out and dig in. Nearby, the Kitchen Witch makes packing the basket effortless with gourmet sandwiches, pints of pasta salad, and homemade cookies. Work off your lunch with a romp in the invigorating tide pools, or let your repast settle as you lie back and wallow in the view. Beach Street; the Kitchen Witch, 4C Summer St., Manchester-by-the-Sea, MA 1944, .
SmarTraveler (www.smartraveler.com)
This is the site to hit before you go anywhere. Updated every few minutes, SmarTraveler.com offers information about tie-ups on local roads and the MBTA. Even better than the concise written alerts are the live video feeds form problem-prone paces like the Central Artery, the Cape Cod bridges, and Route 128. The picture quality is good, though you can't quite discern drivers' obscene hand gestures as they back up on Storrow.
Fin
The food at Fin is subtle at first, but soon shows its adventurous side. Take the chowder. It's a go-to order at any restaurant on the Cape, but Fin uses oysters instead of clams and adds a drizzle of white-truffle oil. That level of detail and savory depth permeates the offerings here, from the flawless pan-seared scallops to the salted-peanut ice cream. 800 Main St., Dennis, MA fincapecod.com.
White Elephant
Leave your car on the Cape. Nantucket’s iconic harborfront resort, and its well-appointed rooms, are no more than 10 minutes from anyplace you’d want to go: Young’s for bikes, the Juice Bar for ice cream, the beach and ferry, too. And if you’re looking for the best on-island massage, you don’t even have to leave the building. 50 Easton St., Nantucket, MA 02554, whiteelephanthotel.com.