The Coonamessett Inn
READ MCKENDREE
After a top-to-bottom 2018 renovation by Lark Hotels brought breezy “modern coastal” décor and integrated technology to every guest room, this old-school Falmouth inn is ready to welcome a new generation of guests. Sip a cocktail on the lushly furnished lakeside patio, groove to live tunes at the on-site music venue, or simply stretch out on the plush king bed after a long day in the sun: Your long-weekend wish is the Coonamessett’s command.
Ocean Edge Resort & Golf Club
Spend one evening lounging around a fire pit on the water-view terrace with your family, and you just might decide to make a stay at this Brewster retreat, centered around a Victorian-style mansion, an annual tradition. And why wouldn’t you, when there are enough amenities here—a Nicklaus-designed golf course, bar-adjacent private beach, luxe day spa, and full-service tennis courts—to make it so you never have to leave?
Yolqueria
Whatever your mark of a great brunch is—gooey cinnamon rolls, killer libations, or an outstanding eggs Benny—this Commercial Street gem delivers. With a background in sourcing organic ingredients for Whole Foods, chef-owner Brandon Quesnell brings the same fresh-and-local commitment to Yolqueria’s menu. The food is worth the wait and the patio is worthy of a cocktail. Paloma picantes and cowboy carnitas, anyone?
Sesuit Harbor Café
Sure, seafood is easy to come by on the Cape. But you're reading this magazine, so you’re looking for the best. Pack your cooler and sunscreen and snag a picnic table at Sesuit Harbor Café: Yes, you’ll wait in a line out the door, sit outside rain or shine, and BYOB, but once those heaping trays of lobster rolls, fried scallops and clams, and Cape Cod Bay oysters are in front of you, you’ll understand.
The Charlotte Inn
This meticulously manicured Edwardian escape is a little pocket of bliss amid the bustle of an island summer. With ornate rooms to wander through and one of the finest restaurants on the island, you may never even make it to the beach.
Harbor View Hotel
ALISON SHAW
Freshly renovated and under new ownership, this standard-bearer of island hospitality is taking luxe to the next level. The 19th-century hotel, which added 26 new rooms, boasts every convenience, including gratis bikes or, for longer rides, a Mercedes SUV.
State Road
Want a meal to match your ideal summer day—unpretentious, nourishing, and simply delicious? State Road has the breakfast for you, from the rustic mushroom toast with a fried egg to the hearty lemon-ricotta pancakes with blueberry coulis.
The Ritz Café
JEREMY DRIESEN
A modest watering hole that islanders depend on after the day’s work is done and the summer crowds have evacuated to the mainland, this institution, which celebrates its 75th anniversary this year, has acquired the patina of legend. If it’s a dive, it’s one that argues there’s more to the designation than peeling paint and a well-worn bar. Located next to the shinier, chicer bars that now line Circuit Avenue in Oak Bluffs, the rough exterior might scare off the faint of heart. And while the aura is arguably friendly, it’s also a bit reckless, hinting at a long history of spirited delights: It wasn’t unheard of, for instance, for regulars to throw a fake wedding at a moment’s notice. Read more 4 Circuit Ave., Oak Bluffs, MA
The Sweet Life
ELIZABETH CECIL
Proprietors Hal and Erin Ryerson, who took over this island favorite from their pals in 2017, are on a mission to make a sweet spot even sweeter. And they’re succeeding thanks to elegant dishes like potato gnocchi with island-raised lamb, basil, and shiitakes.
Hotel Pippa
COURTESY OF HOTEL PIPPA
Opened in 2018, this Nantucket newcomer first charmed us with its well-designed guest rooms, complete with local artwork, smart pops of color, and beds dressed with Fall River–made Matouk linens. But Hotel Pippa, the brainchild of longtime islanders Christopher and Asta Skehel, is much more than a pretty face: Set on the cobblestones of downtown Chestnut Street, it’s also an undeniably lush home base for a weekend spent exploring nearby restaurants, art galleries, and (of course) miles and miles of pristine beaches.
The Wauwinet
We’ve long sung the praises of this Nantucket institution, with its picture-perfect accommodations, unrivaled service, and breathtaking ocean views. And now, thanks to a stunning renovation, there’s even more to love: Debuted in 2019, the reimagined resort shines with marble-tiled bathrooms, custom Pratesi by Rivolta linens, and brand-new furnishings in a beachy-fresh palette of beige and white.
The Proprietors
Flavor and creativity go hand in hand at this island eatery, where dishes such as mushroom-pâté-slathered focaccia and cheesy fried-green tomatoes set the tone for the most innovative brunch menu in town. Top it off with one or two of the Proprietors’ signature drinks (a sparkling rosé cocktail with vodka, passion fruit, and vanilla, perhaps?), and start your Sunday Funday off right.
Afterhouse
Dreamed up by the all-star team behind Nantucket’s Galley Beach, Afterhouse stands apart from would-be rivals with cozy garden-level digs and a curated drink menu full of globally sourced vino. Snag a seat at the wood-topped bar to sip your way through a bevy of Italian whites, French rosés, and Napa reds, all ideal complements to the bistro’s stellar lineup of fish-forward small plates.
Ventuno
Think Nantucket’s fresh catch couldn’t possibly get any fresher? Try pairing it with house-made pappardelle or strozzapreti at Ventuno. Consistently excellent since it opened its doors in 2011, this Italian-inspired eatery continues to wow with hearty from-the-sea entrées such as grilled local dayboat scallops and shrimp with black-truffle salsa. And now with the 2019 opening of sister restaurant Pizzeria Gemelle, the team stands poised to dominate the local pizza game, too.