Chatham Bars Inn
Courtesy Chatham Bars Inn This is the kind of vacation where you throw your car keys in your bag and don't look at them again until checkout time. The beach, the pool, the spa, even the shops and boutiques of downtown Chatham? All within walking distance of the resort's main inn and cottages, where the rooms have all the comforts of home and then some. And if you do get the hankering to go a little farther afield, you can charter one of CBI's boats for some splashy fun. Either way, no car required. See? Now you're relaxing. 297 Shore Rd., Chatham, MA 02633, chathambarsinn.com.
Ocean Edge Resort & Golf Club
There's only one place on Cape Cod you can golf on a Jack Nicklaus–designed course, and it's at this Brewster resort. Ocean Edge's 18 holes will put your skills to the test thanks to a handful of harrowing doglegs. There are straightaways, too (you need at least one birdie, after all), plus the kinds of leafy vistas that will remind you why you came to the Cape in the first place. All you need is one long weekend—tee times are for members and resort guests only—and you're in. 2907 Main St., Brewster, MA 02631, oceanedge.com.
Ceraldi
There's local, and then there's caught-a-few-feet-away-from-your-table local. The latter is what you'll find at this superb tasting-menu spot, which recently came home to P-town after 10 years in Wellfleet. Sample the lobster risotto from chef Michael Ceraldi's seven-course prix fixe in the rose-colored dining room on the wharf, and you'll instantly understand the difference. 9 Ryder St., Provincetown, MA 02657, ceraldicapecod.com.
Baleine
Courtesy A hip natural-wine bar to savor a glass after the beach? Dennis has officially arrived. French for "whale," Baleine is the newest outpost from the folks behind the Pheasant. Despite having caviar service and a grenache blend from the southern Rhône Valley on the menu, the place is refreshingly unpretentious—much like the town itself. 776 Main St., Dennis, MA 02638, baleinecapecod.com.
Chatham Inn
"Old" doesn't always mean musty and dusty. In the case of the oldest continuously operating inn on the Cape, it means plush, understated guest rooms, breakfast in bed, and a gourmet on-site restaurant, Cuvée. A recent redesign of the common areas, drawing inspiration from the Cape's ever-ranging palette, has only upped the ante at this Relais & Châteaux property. But antique details still prevail—see: a restored marble fireplace perfectly complementing the redesigned back bar—and we wouldn't have it any other way. 359 Main St., Chatham, MA 02633, chathaminn.com.
Sesuit Harbor Café
Any true New Englander will tell you seafood is best enjoyed en plein air—especially salt air. A breezy waterfront evening at Sesuit Harbor Café proves that theory: We prefer to pile our picnic table high with fried-to-perfection clams and scallops, plus a succulent lobster roll, some corn on the cob, and a few sushi oysters (topped with soy sauce, ginger, and wasabi) from the lobster-trap-flanked raw bar—all complemented with a BYO bottle of rosé that's been chilling in our beach cooler. 357 Sesuit Neck Rd., Dennis, MA 02638, sesuit-harbor-cafe.com.
Farm Neck Golf Club
Courtesy Farm Neck Golf Club Set on a peninsula jutting out into Nantucket Sound, this course features highly varied terrain—from open grassland to salt marshes, and from forest to the water's edge—making it arguably one of the prettiest courses in New England. But looks aside, it's also the island's nexus of power. Presidents (Clinton and Obama), celebrities (Bill Murray and Larry David), and sundry bigshots and billionaires regularly play here. Although it's nominally a private club, non-members can play, too—if you can nab a tee time. One Farm Neck Way, Oak Bluffs, MA 02557, farmneck.net.
Harbor View Hotel
The grande dame of Vineyard hotels has anchored the east end of Edgartown for more than a century. But a recent renovation ensures your stay will feel anything but old-fashioned: Refreshed guest rooms and refined finishes feel luxe and relaxed, while amenities include a Cap-Ferrat-worthy swimming pool. Views of the harbor and its iconic lighthouse remain unparalleled. You'll pay upward of $1,000 a night in high season for a reason. 131 North Water St., Edgartown, MA 02539, harborviewhotel.com.
El Barco MV
Nothing hits the spot quite like a frozen piña colada on a hot summer day—actually, the $14 margs (spicy or sweet) and mezcal Old Fashioneds from this casual taqueria do the trick, too. Opened in 2024 just steps from the Steamship Authority, it's the ideal place to stop in for a refreshing drink on your way on or off the island. And of course, we wouldn't blame you for tiding yourself over with a little snack, whether it's the carnitas burrito, short-rib tacos, chips and guac, or all of the above. 16 Union St., Vineyard Haven, MA 02568, elbarcomv.com.
Summercamp
Courtesy Lark Hotels Remember what summers were like as a kid? You will after a stay at this whimsical waterfront hotel in the heart of OB. Visual surprises abound around every corner (see: the cool tennis-racket artwork and hanging egg chairs), and games like Ping-Pong, Jenga, and Twister, along with a thoughtfully stocked canteen, help the place live up to its name—without the mosquito bites and mess-hall food. 70 Lake Ave., Oak Bluffs, MA 02557, larkhotels.com.
The Ocean Club Restaurant & Bar
You don't have to book a cruise to feel like you're dining inside an art deco ocean liner. With its swanky interior featuring a domed ceiling and lots of stained glass, this restaurant inside a converted historical bank is a splashy new addition to the island's dining scene, courtesy of Boston nightlife king Patrick Lyons. The tempting surf-and-turf menu features items like prime Brandt steak frites and salmon almondine—best washed down with a vintage Negroni, naturally. 75 Main St., Vineyard Haven, MA 02568, oceanclubmv.com.
The Back Door at the Homeport
Photo by Elissa Garza The best-kept secret in Menemsha? This local landmark offers its most beloved dishes to go. Alongside upscale dine-in favorites like chilled green gazpacho and the refreshing lobster Cobb, you'll find beach-perfect handhelds like crab-cake sandos and lobster rolls (mayo or butter). It takes all the guesswork out of planning a picnic for that age-old Martha's Vineyard tradition: watching the sun sink into Vineyard Sound from the town beach. Just keep in mind that Chilmark is dry, so pack your own libations. 512 N. Rd., Menemsha, MA 02535, thehomeportmv.com.
76 Main Ink Press Hotel
Photo by Paige Harding, PAHCREATIVE It's not just the location we love—perched a stone's throw from the harbor, shops, and restaurants of downtown—but the way this boutique hotel blends a polished coastal aesthetic with deeply rooted character. Set within a restored sea captain's home, the main house anchors a horseshoe of intimate cottage suites that frame a charming back patio. The hotel's theme honoring Nantucket's publishing history sets it apart even further. Add in a convenient text-the-staff feature and it becomes the perfect home base for exploring the island with ease. 76 Main St., Nantucket, MA 02554, islandhotelcollection.com.
Straight Wharf Fish
If your next Nantucket meal were a simple mathematical equation, it would go something like this: bright and sunny interiors + water views + fresh, locally sourced seafood = Straight Wharf Fish. Headed into its third season, this chic seafood shack excels at making the approachable fantastic. Think: steamed New England clams with fries, or onion rings with caviar and crème fraîche. Just save room for dessert. We got the inside scoop that soft-serve ice cream is hitting the menu this season. 4 Harbor Sq., Nantucket, MA 02554, straightwharffish.com.
Billie’s
If any restaurant has had to learn how to run before it could walk, it's Billie's, Nantucket's newest steakhouse. After opening mid-season last year, it still managed to seamlessly roll out a menu of decadent steaks and sides (don't leave without ordering the creamed spinach). What has us especially jazzed for this year are expanded offerings, including a raw-bar tower and a highly anticipated dessert lineup (cookie skillet, anyone?), as well as a newly redesigned patio for al fresco dining. But we're sure the chandelier-bedecked indoor dining room will remain the main draw—the kind of place you'd meet Don Draper for a drink, with a vibe that's equal parts swanky and effortlessly cool. 20 Broad St., Nantucket, MA 02554, billiesnantucket.com.
Cisco Brewers
Courtesy Cisco Brewers A trip to Cisco is a Nantucket rite of passage—and luckily, getting there couldn't be easier. Snag a seat on the Cisco shuttle (or should we say party bus?) for a free ride from downtown Federal Street to the brewery. You'll arrive a short drive later to find multiple bars serving cocktails, on-site-brewed beers, spirits, and wine, plus live music, an impressive souvenir shop, food trucks, and yard games that make it fun for the whole family. 5 Bartlett Farm Rd., Nantucket, MA 02554, ciscobrewers.com.
The Nantucket Hotel + Resort
Taking the stairs up to this downtown hotel feels like entering a world where every detail has already been taken care of—the kind of place where you can truly switch off, knowing the staff has thought of everything. As at any good island resort, the interiors are simple yet elevated, while the amenities are equally as impressive: two pools (one for families, one reserved for adults), a full fitness center and spa, a complimentary shuttle service to local hot spots (in an antique vehicle to boot), Frette linens, a kids' club, and an on-site restaurant. We told you they thought of everything. 77 Easton St., Nantucket, MA 02554, thenantuckethotel.com.
Miacomet Golf Course
As Nantucket's only public 18-hole course, Miacomet draws its true character (and challenge) from the island's natural elements. Just a mile from the often-untamed south shore, the ever-shifting coastal winds can transform each round, ensuring no two games are ever quite the same. A lively restaurant and bar provide the perfect setting to unwind, while the putting green offers an ideal place to sharpen your short game. If the weather refuses to cooperate, indoor simulator bays allow you to tee up on world-famous courses from around the globe, though after experiencing Miacomet, you may find there's nowhere else you'd rather play. 12 W. Miacomet Rd., Nantucket, MA 02554, miacometgolf.com.