Chatham Bars Inn
Chatham Bars Inn Even if you don’t take advantage of the $50,000 (yes, you read that right) “Best-Ever Cape Escape” travel package offered at this iconic seaside resort, you’ll still feel like a million bucks when you book a stay here. Why? Well, let us count the ways. First, there’s the gorgeous private beach with cabanas. Then there’s the luxe accommodations, which range from ocean-view rooms in the historical Main Inn to shingle-style cottages, and the foodie-friendly dining experiences. Cap it all off with a sea-salt scrub at the sumptuous on-site spa, which comes with its own Zen-like pool area, and you’ll be counting the days until you can visit again. 297 Shore Rd., Chatham, MA 02633, chathambarsinn.com.
Ocean Terrace
Sip a Cape Codder with Cape Cod Bay as your backdrop at the outdoor bar of the elegant Ocean Edge Resort & Golf Club. Facing toward the Brewster Flats, it enjoys a West Coast sunset (sundowner, anyone?), making it the ideal place to toast 18 holes well played or an idyllic day on the beach. Add on any of the menu’s New England classics, including oysters on the half shell and clam chowder, and you’ve got a hole in one. 2907 Main St., Brewster, MA 02631, oceanedge.com/dining/ocean-terrace.
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.
Wicked Waves Cape Cod
Courtesy of Wicked Waves Cape Cod Exciting enough for the older ones but tame enough for the little tykes, this water park promises fun for any age. We mean grownups, too, with cabanas for rent, multiple food options, and even an adults-only swim-up bar. (Parents will also appreciate that the water is monitored and tested for cleanliness throughout the day.) Even more reason to skip the beach: This season, Wicked Waves is unveiling five new slides that promise to twirl, undulate, and discombobulate in equal measure. 518 Main St., West Yarmouth, MA 02673, wickedwavescapecod.com.
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.
The Nantucket Hotel + Resort
The Nantucket Hotel is no stranger to compliments, having scooped up multiple awards from this magazine and other outlets, but we’re dishing them out again for the hotel’s awesome extras (see: shuttle service to the beach and all around town, s’mores for littles around the porch fire pits, and handwritten notes from the GM upon arrival). That said, the newly redecorated lobby, full spa, two heated pools, family-friendly rooms, and lively restaurant are certainly worth the praise, too. 77 Easton St., Nantucket, MA 02554, thenantuckethotel.com.
The Nautilus
Georgie Morley What happens when you combine fresh local seafood with Asian flavors in a traditional Mexican dish? This isn’t a riddle; it’s Nautilus’s mouthwatering nori-wrap tacos filled with tempura-fried local oysters. The meal is just one of many gems on a menu full of East-meets-West mash-ups, including steamed Berkshire pork–belly buns — it’s the sweet-and-savory coffee mayo for us — Peking-inspired whole duck, and a blue-crab fried rice that’s what island dining dreams are made of. 12 Cambridge St., Nantucket, MA 02554, thenautilus.com.
Ethos Nantucket
Strutting into its second summer season, this eclectic wine bar’s speakeasy vibe isn’t just for oenophiles. Cocktail connoisseurs will appreciate the refreshing drinks list, while foodies can dig into a menu featuring freshly shucked local oysters, caviar, and salmon crudo. Our idea of the perfect pairing, though, has to be the gooey grilled cheese on local pink-salt sourdough with a glass of Il Monticello, a juicy Italian red with notes of dusty cherry. 18 Broad St., Nantucket, MA 02554, ethosnantucket.com.
Nomad
Wendy Mills Photo It may be chaotic in downtown Nantucket on a typical summer day, but inside the apparel and home-goods store Nomad, all is calm. Set in soothing coastal tones, the store offers a place to rest your eyes on a neutral palette of sophisticated home accessories, including throws, pillows, and glassware. Worldly sourced loungewear, jewelry, and sandals, meanwhile, epitomize what we’d call Nantucket barefoot elegance. 17 Centre St., Nantucket, MA 02554, nomadnantucket.com.
Faraway
Matt Kisiday The main guest house at this chic boutique hotel may date to 1742, but the interior design is firmly planted in the 21st century. Spread out between six buildings, the property features a central swimming pool and perfectly manicured grounds, with sleek common areas that hint at stylish rooms decorated in warm, neutral tones and appointed with five-star amenities. 23 Kelly St., Edgartown, MA 02539, farawaymarthasvineyard.com.
Chilmark Tavern
One bite of the burger with Vermont cheddar on a brioche bun, the juicy wings slathered in a honey-jerk dry rub, or the island’s best Bolognese, and you’ll get why this eatery is a favorite hangout of Larry David, Bill Murray, and billionaires bored of their personal chefs’ cooking. Just be sure to show up with a nice bottle of booze, as Chilmark is a dry town. 9 State Rd., Chilmark, MA 02535, chilmarktavern.com.
Flying Horses Carousel
Lucian Nastasi Grabbing the brass ring is considered a Vineyard childhood rite of passage, and for good reason. One of the oldest carousels in the country, Flying Horses was moved to its current location in Oak Bluffs from Coney Island in 1884 and has been charming children and adults with its nostalgic charm ever since; the handcarved horses have glass eyes and manes and tails of real horsehair. The adjoining arcade offers further diversions once the room stops spinning. 15 Lake Ave., Oak Bluffs, MA 02539, vineyardtrust.org/property/flying-horses-carousel/.
Town Bar & Grill
The homey, shingle-clad exterior of this unpretentious hang beckons locals and tourists alike to come on in and stay awhile. And stay they do, lingering over creative cocktails — including a seasonal sangria with dark cherry and plum wine — live music, and fresh, handrolled sushi (also available as platters to-go for the ultimate beach snack). 227 Upper Main St., Edgartown, MA 02539, townbarmv.com.
The Seven Sisters
Born-and-bred Vineyarder Ty Sinnett views her store not only as a shop but as a mission to support slow fashion and design. As such, the worldly goods on offer here are as thoughtfully sourced as they are gorgeous, from sustainably crafted hand towels to zero-waste hair accessories. After all, what’s a better gift than helping to preserve our planet? 19 Main St., Vineyard Haven, MA 02568, thesevensisters.co.