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.
Coast Guard Beach
Thoreau once walked the 40 miles of the Cape's pristine eastern coast and wrote a whole book on the experience. JFK, also a fan, ensured that the shoreline and its marshes, freshwater ponds, and lighthouses were preserved for future generations. On the southern end of the protected strip sits Coast Guard Beach. With its rolling dunes and ever-shifting conditions—roaring one day, serene the next—it's a breathtaking place to stroll, lounge, picnic, or surf. Doane Road, Eastham, MA 2642, .
Añejo
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.
Añejo
Trade your mimosas for margaritas at this brunch hot spot, which serves up creative Mexican cuisine with a Cape twist (see: the quahog rellenos and chipotle-laced lobster bisque). Dine beneath a centuries-old weeping beech tree at the Hyannis outpost, or sit back and people-watch, Paloma in hand, from the Falmouth location’s patio — either way, you’ll find a fun atmosphere that makes every Sunday feel like a party. Multiple locations. anejo.cc.
Jim Horgan
Front Street's bar (260 Berkeley St., Boston) is a quiet, secure haven, protected by Horgan. A five-year veteran of the bartending wars of Boston and Cape Cod, Horgan knows his regulars and what they drink, and he protects their privacy. "This isn't a pickup bar," Horgan says. "People come here to relax. Single women come in by themselves and trust me to see they're left alone. People know that no one will bother them here." Front Street, 260 Berkely St., Boston, MA .
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.
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.
Leonessa
Husband-and-wife team Diego Mota and Taylor Amara have combined their extensive culinary experience to create this cozy slice of Italy that avails itself of all the fresh seafood and produce Cape Cod has to offer. The lively bar scene is where you’ll want to begin the evening, while the dinner menu ranges from starters like cherrystone clams casino to larger dishes such as handrolled strozzapreti with prime beef-and-veal ragu and haddock Milanese. Mangia bene! 43 Main St., Yarmouthport, MA 02675, leonessacapecod.com.
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.
The Beachcomber
When President John F. Kennedy established the Cape Cod National Seashore in 1961, he effectively curbed future development in the area. The preexisting Beachcomber, however—housed in an 1897 former lifesaving station—was allowed to keep one of the few commercial permits available on the Atlantic-facing coast. So the next time you’re slurping Wellfleets, enjoying live music, or sipping a piña colada at this popular spot, toast JFK for the special setting and views of the open ocean. 1120 Cahoon Hollow Rd., Wellfleet, MA 2667, thebeachcomber.com.
Sundae School
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.
Coonamessett Inn
With its glossy, red shingles and gabled roofs, the Coonamessett Inn is the epitome of old Cape Cod, a perfect setting for high-style weddings and anniversaries alike. But you needn't wait for a special occasion: Sunday brunch features an array of delicious classics, from make-your-own omelets and baked salmon with special weekly sauces like beurre blanc or citrus, melon, and mango, to oversized fruit plates and gorgeous renditions of sweet favorites like chocolate mousse and carrot cake. 311 Gifford St., Falmouth, MA 2540, capecodrestaurants.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 .
Clove & Creek
You’re on your way to your friend’s beachfront pad in P-town, and you forgot to pick up a host gift. Think fast — where do you go? That’d be this apothecary-style shop, which arrived on the Cape by way of the Hudson Valley last year, bringing with it a curated lineup of unique goods (think: woodblock-print greeting cards, hot-spring-inspired bath salts, and zucchini relish). This is one New York import that we’ll gladly welcome to our salty state. 353 Commercial St., Provincetown, MA 02657, cloveandcreek.com.
Fishermen’s View
Come for the view, stay for the vibe, order the seafood. That’s all you need to know to enjoy an evening at Fishermen’s View, situated on the canal in Sandwich. Opened in 2016 by brothers and fishermen Bob and Denny Colbert, the menu emphasizes fresh, local catch, most of it unloaded at the docks below the restaurant. An inviting atmosphere awaits on the patio in the warmer months with live music and an outdoor bar, but sunsets over the canal (accompanied by stuffed Cape Cod cherrystones or a lobster "knuckle" sandwich) are sweet any month of the year. 20 Freezer Rd., Sandwich, MA 02563, fishermensview.com.