Sundae School started as a mom-and-pop operation—and a reason for founders Paul and Andrea Endres, then living in Milton, to spend their summers on the Cape. Three decades and three stores later, it's a full-time family affair (at some point, each of the Endreses' five kids has worked behind the counter). The shop's celebrated ice cream is made fresh, and in limited amounts; among the most heavenly flavors are sweet cream, ginger, créme de menthe chip, and any of the berry blends. 606 Main St., Route 28, Harwich Port, MA 2646, sundaeschoolicecream.com.
Arnold's Lobster & Clam Bar
Just as hot dogs are a Fenway favorite, it would be silly to skip clams on Cape Cod. And among the dozens of small shacks, Arnold's remains a standout. This quality-conscious spot now has a dining room and screened-in patio—as well as lengthy lines (it's worth the wait, though). Prepare to get messy while scarfing Wellfleet oysters, lobster rolls, and, of course, the famous Arnold's fried clams. 3580 State Hwy. (Rte. 6), Eastham, MA arnoldsrestaurant.com.
Pump House Surf Shop
Opened with the money earned from a dish-washing job by a guy who started surfing on the Cape when he was 5, the Pump House has surf attitude. All the salespeople surf, of course; most wear board shorts in the store, whose back wall is stacked with 100 boards ready to throw on top of the VW and take to the nearest beach, five minutes away. The Pump House also offers rentals, repairs, and lessons, and sells apparel, Frisbees, and the wetsuits that are standard gear for any true New England surfer. 9 Cranberry Highway (Rte. 6A), Orleans, MA pumphousesurf.com.
Chatham Bars Inn
Massages and facials are delightful—until they cut into your precious sun time, that is. Thankfully, the Spa at the Chatham Bars Inn offers the best of both worlds. The facility's outdoor plunge pool, surrounded by lush gardens, is a tranquil way to take in the beauty of the Cape after an aah-inducing rubdown. Al fresco treatments in private cabanas, meanwhile, maximize the therapeutic benefits of the great outdoors. 297 Shore Road, Chatham, MA 2633, chathambarsinn.com.
The Urban Hound
We’ve been there countless times: We want one last cuddle with Fido before leaving for vacation, but instead he wriggles out of our hands like an eager camper, more than ready to sniff butts and play with his buddies. These are the moments when pet parenting can be slightly heartbreaking (My puppy! He’s all grown up!). When Urban Hound is hosting him for the weekend, however, that goodbye is a little easier to handle: The luxury accommodations at the pet hotel and daycare facility—which features two indoor play parks and 1,000 square feet of outdoor space—are matched only by the fantastic trainers and staff, who are more than qualified to play in loco petrentis. 129 Malden St., Boston, MA 2118, urbanhounds.com.
In a neighborhood that's more about hot dogs than haute cuisine, it can be hard to get a decent meal. That's where Audubon Circle comes in. This darkly lit, sleekly cool restaurant with the long slate bar has a small but satisfying menu of dressed-up pub grub, from the downright delicious burger with spicy home fries to the rare seared tuna with garlic mashed potatoes. The legendary pot stickers (dumplings and steamed vegetables served in a paper takeout container) can provoke food fights—over who gets the last bite. And thanks to the expertly mixed drinks and ample supply of local and national beers on tap, there's plenty to please diners and drinkers who long for more than the watered-down suds at Fenway. 838 Beacon St., Boston, MA auduboncircle.us.
If brunch is the most civilized way to dine, the Harvest is the most civilized place to have brunch. First there's the restaurant's lovely garden patio, which in warm weather offers a leafy retreat from the traffic of Harvard Square. Then there's the table presentation. No paper napkins and messy tabletops here—brunch at the Harvest is a white-linen, Sunday-best affair. But it's the menu that renders this restaurant a class above, with its three-course, prix-fixe ($33) menu of gourmet takes on classic dishes. The eggs Benedict, for instance, are served not one but two ways: crab and avocado on one orb, smoked ham and asparagus with roasted red pepper hollandaise on the other. Omelets come with such citified ingredients as wild mushrooms, spring onion, or pancetta. It's the final course—dessert—that makes this tradition a proper indulgence, from the milk chocolate panna cotta to the irresistible classic chocolate layer cake. 44 Brattle St., Cambridge, MA harvestcambridge.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.
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, .
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.
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.
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.
There's finally authentic Mexican on the Upper Cape thanks to this bustling spot in Falmouth Center, which skips the gimmicks and gloppy cheese in favor of fresh, local seafood and a creative Sunday brunch menu with a twist—and a kick. Go for the gloriously runny eggs Benedict topped with smoky braised pork and chipotle hollandaise, or French toast laced with tequila-fried bananas. Bonus: Kids get a free chocolate taco (you might, too, if you ask politely). 188 Main St., Falmouth, MA 02540, anejomexicanbistro.com.