A local legend offers eight spots for first-timers and returning visitors alike

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Word of Mouth: Nantucket According to Cisco Brewers’ CEO, Jay Harman

A local legend offers eight spots for first-timers and returning visitors alike

Emily Gerard

2 September 2024

Bestselling author Elin Hilderbrand has been writing about Nantucket, where she lives, for decades. Her enormously popular beach reads about the exploits of “the misbehaving moneyed class” have not just sold millions of copies; they’ve also given rise to a cottage industry of tours. Fans now travel to the tony vacation destination eager to experience its distinctive brand of New England coastal charm for themselves. This summer, many had the chance to meet Hilderbrand in person at a book party she hosted at Cisco Brewers. The beloved combo brewery, winery and distillery is as famous as Hilderbrand is, at least locally. And its CEO, Jay Harman, is another unofficial ambassador for the island. He’s a bon vivant who seems to know everyone, everywhere he goes—but mostly, they come to him.

Cisco Brewers is so popular, in part, because it’s so many things. It’s a place to see live music, fuel up at food trucks, and sample some of the world’s best whiskey, which, yes, is made here—though the beer seems to get all the attention. In case that wasn’t enough on his plate, Harman recently branched out into vacation rentals with Cisco Surf Suites. The colorful apartment-style accommodations in the center of town are perfect for families or groups of friends.

Harman told COOL HUNTING it’s “the perfect property” to round out his portfolio because he wanted a convenient location “where guests can enjoy direct access to all that downtown Nantucket has to offer.” He offered up a jam-packed weekend itinerary ideal for first-timers and returning visitors alike.

Lemon Press

Everyone on Nantucket wants to start their day at Lemon Press, and for good reason, so make reservations accordingly. The cheerful and always-buzzing restaurant uses plenty of locally farmed produce in its inventive, Middle Eastern-influenced menu. This author’s party ordered orange blossom waffles for the table, but they were largely ignored in favor of a savory standout: the Persian breakfast pita stuffed with duck confit hash, feta cheese and date chutney. Dates were also a welcome addition to the delicious and dramatic-looking black “Blind Date” smoothie with bananas, tahini and activated charcoal. 

Nantucket Mermaids

Nantucket Mermaids began as a boat cleaning service decades ago; now, owner Leah Collins is the proud operator of Nantucket’s largest fleet of yacht charters. Friendly staff will help make sure your experience is luxurious and relaxing, whether you’re looking to island-hop or drink champagne while enjoying a glittering sunset. 

Millie’s 

If boats aren’t in the budget or bikes are simply more your speed (or you want to do it all), pick them up at Cook’s Cycles and take the scenic route to Madaket Beach. There, you’ll find Millie’s, an elevated beachside restaurant, where you can refuel with fried shrimp po’boys and lobster rolls. 

Cisco Brewers

Ask for the shortcut to take you from Millie’s to Cisco Brewers and feel smug about everyone else navigating traffic to get there. Cisco is where you want to be on a weekend evening, dancing to live music in the fresh air while nursing your choice of local bevvies. Sure, the Whale’s Tale Pale Ale has a cult following. But it’s a shame more people don’t know that Notch Whisky is distilled on premises, too—now that’s the really good stuff. 

Brotherhood of Thieves

Known colloquially as “Brotherhood,” the historic whaling bar and tavern dating back to the 1840s is a crowd-pleasing choice for dinner groups. There’s something for everyone on the menu, but don’t miss the creative sushi rolls highlighting local fish—or check out the pub-style menu at the beer garden outside. 

The Chicken Box

Whether you’re a resident or visitor, young or old, everyone ends the night at The Chicken Box in search of cheap(ish) drinks and a bumping dance floor. It might be a local band that has the crowd on its feet, or a big name passing through. Either way, it’s the perfect place to make sure you have stories to tell at brunch the next morning.

Galley Beach

Pretty tables are parked directly in the sand at Galley Beach under a sweeping muslin tent. It’s been a Nantucket landmark for a century and yet the menu is fresher than ever; we loved the clam chowder and a perfect lobster omelet with tarragon and creme fraiche. After brunch, guests need only move a few feet farther into the sand for a coveted perch under chic beach umbrellas. A dip in the Nantucket Sound is the best hangover cure—but if it fails you, servers are more than happy to supply you with a little hair of the dog. 

Cru

Cru bills itself as Nantucket’s premier oyster bar, and among stiff competition it may just be true. Getting a waterfront reservation here is a flex worthy of a special occasion. Local littlenecks are tiny and sweet, while the oyster selection is wide-ranging. We also loved the lobster fettuccine and New York strip steak with crunchy bronzed duck fat fries. By the time we were finished with dinner, a flock of fabulously dressed individuals had arrived to dance on the bar.