Wequassett Resort & Golf Club
Courtesy Just when you thought Wequassett couldn't possibly get any dreamier, this oh-so-swanky resort, nestled along Pleasant Bay, unveiled a dazzling $12 million makeover just in time for its 100th birthday. Designed by Boston interiors firm Reider + Co., guest rooms are now bedecked in linen, grasscloth wallcoverings, and a palette of coastal blue, with new soaking tubs in the suite's bathrooms. The amenities outside the rooms, meanwhile, continue to make a splash: Jump into one of the two gorgeous pools, enjoy a five-star meal at Twenty-Eight Atlantic, or take the free boat ride to Outer Beach for a day of fun in the sun. 2173 Head of the Bay Rd., Harwich, MA 02645, wequassett.com.
Lune
For decades, the mid-Cape's best restaurants were seafood shacks; truly fine dining required a long drive on Route 6. That's no longer the case thanks to Lune, a newly christened James Beard Award semifinalist where imaginative seasonal tasting menus are served inside a former gas station garage. Among the small-plate standouts? Scallop crudo, tomato tartine, and roasted monkfish, as well as desserts such as Hoodsie Cups amped up with sea-salt caramel and Chantilly cream. 587 Main St., Dennis Port, MA 02639, lunecapecod.com.
Mac’s on the Pier
Want to enjoy your fried clams mere steps from the fishermen hauling them off the boat? Then make it a point to stop at Mac's on the Pier, where you can tuck into pristine seafood on a picnic table overlooking Wellfleet Harbor. The menu has the classics, of course—fish and chips, fried scallops, whole-belly clams—but we also love to mix it up with dishes such as seared yellowfin-tuna tacos and fried-fish burritos. 265 Commercial St., Wellfleet, MA 02667, macsseafood.com.
AWOL
The Province Lands marshes make up one of the Outer Cape's most uniquely beautiful landscapes, and AWOL in Provincetown's rooms have a front-row seat to them. The boutique hotel offers understated yet luxe lodgings—plus a heated pool and fire pits outside—that overlook the vibrant green grasses and cerulean-blue waters. Though it's a short walk to town, you may never want to leave, especially if you book the Lark Suite, complete with a roof deck. 59 Province Lands Rd., Provincetown, MA 02657, larkhotels.com/hotels/awol.
The Beach Bar at Ocean Edge Resort & Golf Club
Cocktails just taste better with a gentle, salty breeze in your hair, and Ocean Edge's Beach Bar is one of the best spots for both. Pick your poison—a cranberry mojito or pineapple-strawberry vodka smash, perhaps?—and enjoy it while watching the sun set over Cape Cod Bay. On a clear day (and presumably with a clear head), you can see all the way to P-town. 2907 Main St., Brewster, MA 02631, oceanedge.com.
The Beachside Hotel
Photo by Matt Kisiday Having just opened its doors in early May after a year-long renovation, this Brant Point landmark is fresh-faced and ready for its close-up. Calling itself a “love note to the great American summer," the hotel now offers guests complimentary bikes, all-day poolside dining, and an on-site game room and arcade, among other plush amenities. Brought to life by Blue Flag Capital (the team that's revitalized multiple hotels on island, including Faraway, Blue Iris, and Life House), the swoon-worthy new guest rooms were redesigned in soft hues with midcentury-modern finishes that have a hip yet relaxing vibe—just what you want for an island vacation. 30 N. Beach St., Nantucket, MA 02554, thebeachside.com.
Cisco Brewers
It's a party, and you're invited! Well, think more along the lines of a “block party" with live music; multiple bars serving craft brews, wine, and cocktails; food trucks; lawn games for the kids; and a free shuttle from downtown. Here, the notion of “après beach" thrives: Expect sandy ankles, loose coverups, and drinks raised high. Did we mention it's dog-friendly, too? 5 Bartlett Farm Rd., Nantucket, MA 02554, ciscobrewers.com.
Next Level Watersports
Courtesy It's called Next Level Watersports for a reason. Longtime friends Jake Hoefler and Jon Beery head into their 10th summer season by kicking family fun up a notch with wakeboarding and tubing, hydrofoiling, and more, all in the calmer (and safer for beginners) waters of Nantucket Harbor. Three-hour sessions include hands-on guidance and the promise of lifelong new skills—exactly the kind of waterborne experience you wish you had as a kid. 24 Washington St., Nantucket, MA 02554, nextlevelwatersports.com.
The Wauwinet
One hundred and fifty years young this year, this classic Nantucket resort sits perched at the head of the harbor—which is just 20 minutes from downtown on the hotel's complimentary shuttles, and a few minutes on its boat, The Wauwinet Lady, which offers a daily gratis ride at 4 p.m. This geographical separation is what may, in fact, preserve the classic elegance that is the Wauwinet. Lucky guests enjoy high-end service, water-view rooms with crisp interiors, complimentary BMWs for navigating the island, harbor sails and tours, fine dining at Topper's, and a gorgeous green lawn appointed with padded loungers from which to stretch out and enjoy the harbor view—with a cocktail or two, naturally. 120 Wauwinet Rd., Nantucket, MA 02584, wauwinet.com.
Galley Beach
There are plenty of restaurants on Nantucket with top-notch food, but when there's something to be celebrated (no matter how small), locals go to Galley Beach, and for good reason. This finedining, open-air restaurant sits directly on the beach, offering unobstructed views of Nantucket Sound as delicious as the carefully curated chef's menus served daily from 11:30 to close (we recommend the miso-butter-poached lobster). Even better: New this year, you can make a day of it by adding on beach service (with a chair and umbrella rental) until 5 p.m., begging the question of what we can toast to this summer. The answer? Everything. 54 Jefferson Ave., Nantucket, MA 02554, galleybeach.net/home.
The Back Door at the Homeport
Photo by Elissa Garza An island stalwart since 1930, the Homeport is now operated by the Boston-based Aquitaine Group, which has elevated traditional clambake cuisine to unprecedented culinary heights. All of it is available through the Back Door, the restaurant's takeout option, so you can enjoy steamers and lobsters on the beach, or serve it at home on your own back deck. 512 N Rd., Menemsha, MA 02535, thehomeportmv.com.
Beach Road
On an island where G&Ts are about as complex as cocktails get, the libations at this Vineyard Haven spot are a seriously delightful surprise. Standouts include the “Mad Men," featuring strawberry-black-pepper-infused Herradura reposado, celery, Ancho Reyes Verde, and lemon; and the cheekily named “Fowl Play," which blends duck-fat-washed Eagle Rare bourbon, maraschino, Amaro Nonino, and orange. If you consider yourself a cocktail connoisseur, picture yourself here as the sun dips below the horizon over Lagoon Pond; it's pretty much the perfect ending to a day. 79 Beach Rd., Vineyard Haven, MA 02568, beachroadmv.com.
Faraway
Photo by Matt Kisiday Since we tapped Faraway for the best hotel award last year, the chic Edgartown getaway has earned a Michelin Key, and no wonder. With contemporary décor that eschews the usual nautical clichés, three superb dining options, a swanky pool scene, and a location steps away from Edgartown, it's a boutique oasis without equal on the island. The cushy rooms, spread out over six buildings, boast amenities like Byredo products, Victrola record players with Bluetooth speakers, and fully stocked mini bars. We'll toast to that. 23 Kelly St., Edgartown, MA 02539, farawaymarthasvineyard.com.
Island Spirit Kayak
Want to get them off their screens and onto the water? Island Spirit's kayaking and paddleboard tours should do the trick. Departing from Little Bridge in Oak Bluffs, daytime and sunset excursions are both incredibly scenic, but our favorite adventure is the evening “glow tour." Clear-bottomed kayaks and paddleboards offer a fish-eye lens into the life aquatic, illuminated by LED glow lights. Edgartown Oak Bluffs Road, Oak Bluffs, MA 02557, islandspiritkayak.com.
Outermost Inn
Looking to plan an unforgettable date night (or an even more unforgettable proposal)? Perched atop the magnificent Aquinnah Cliffs at the farthest reaches of the island, this intimate restaurant delivers romance and spectacular views in spades. And top-notch dining: Last year, when chef Christian Fischhuber, an alumnus of Le Cirque, began his tenure, he applied his philosophy of simple, honest cooking that lets local ingredients shine. That's translated into dishes like delicate stuffed zucchini blossoms and a surf-and-turf for two (lobster Thermidor and a 28-ounce T-bone) that's practically a love letter on a plate. 81 Lighthouse Rd., Aquinnah, MA 02535, outermostinn.com.