Dennis Cycle Center
The best — and some might say only — way to rent a bike on Cape Cod is from a place right along the rail trail. While there are several options for doing just that, Dennis Cycle Center gets high praise for its wide selection of two-wheelers and accessories — including plenty of options for the littlest cyclers — reasonable rates, and ultra-friendly staffers. Extra props for the expert repair services, for those who need a tune-up on their own summer ride. 249 Great Western Rd., South Dennis, MA 02660, denniscyclecenter.com.
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.
Paul Connors, Radius
For the second year in a row, we've been unable to resist the delectable charms of Radius patissier Paul Connors. The mere mention of his name in Greater Boston sweet-tooth circles produces a range of reactions from barely audible moans to downright drools. Chef Connors' meal-ending treats are passionate, inspired, and sometimes even quirky: The guy is as adept at "candy cape mushroom ice cream sandwiches" as he is at classic creme brulee. And he's a team player: Connors' desserts are the perfect complement to executive chef Michael Schlow's elegant continental dishes, never overshadowing their savory flavors. Calling all pastry chefs: Consider the bar raised. 8 High Street, Boston, MA radiusrestaurant.com.
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.
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.
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.
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.
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, .