Posted on
September 19, 2025
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Trip Ideas
Every summer, IgoUgo Editor Charlie Davidson and his family spend time off the East Coast soaking up the Nantucket spirit. This year, he spent 10 not-always-sunny days on this island where, as the locals say, fog happens. The sunsets are glorious, the beaches are pristine, and the food is, apparently, plentiful.
While life does move slower on this island, it is not the Caribbean. Thirty miles off the coast of Massachusetts, in the chilly Atlantic, lies Nantucket. The name means “faraway land,” and with good reason. Though more accessible than ever with hydrofoil fast ferries and constant flights into ACK, Nantucket still possesses an otherworldly charm that harks back to its days centuries ago as a hub of the whaling and fishing industries.
Once you arrive on the wharf, you can stroll past the bike shops and hit the north end of town. To start our day off right, my brothers and I like to head to the Juice Bar. Specializing not in juice but in ice cream, the Juice Bar makes some of the thickest, maltiest frappes (milkshakes) in the world, and handmade waffle cones to support any of the variety of ice creams, sorbets, and frozen yogurts on offer.
If you arrive via Hy-Line, on the other side of the wharf, you’re just steps away from the origin of the now ubiquitous Nantucket Nectars. The AllServe shack, as it was dubbed by Tom and Tom, has moved from the wharf, but is still nearby selling its purple wares. If you’re looking for some more substantial grub, and have a craving for seafood—you’re on an island, after all—the Ropewalk serves up some of the freshest around. I love the calamari with the sweet-and-spicy soy, honey, ginger, and scallion dipping sauce. While you’re there, wash down those cephalopods with some of the local Cisco Brewers’ Whale’s Tale Pale Ale on tap, and look out at the exorbitant yachts moored in the harbor.
And if you need lunch on the beach, the best sandwiches on the island are also on the Straight Wharf. Provisions, at Harbor Square (hidden behind the large gazebo), can fix you a Turkey Terrific on Portuguese bread. A Thanksgiving meal in a sandwich, this beast is not for those who eat like the birds of the island. Packed with sliced turkey, stuffing, cranberry sauce, and mayo, this sandwich should tide you over until dinner.
Of course, you didn’t come all the way out here just to eat—or maybe you did, but Nantucket has some of the country’s most beautiful beaches too. Save for a few places where bluffs or protected dunes abut the shore, the coast is practically all pristine beaches. Have a dip, but remember that you’re 30 miles off the coast in the Atlantic; chances are, it’s chilly, and there may be an undertow, so be sure you know where the lifeguards are.
And if being a beach bum isn’t your thing, there are plenty of other activities to float your boat. To cast a line and reel in some game, call up Captain Tom, who can get you some of the great bluefish that swim in the area—they’re great for grilling! Of course, with all that eating, you may need a way to burn some calories aside from baking in the sun. For exercise, and to take some of the traffic pressure off the small roads, bike or run on the well-maintained bike paths.
Once you’ve gotten home from the beach and showered off the sand and salt, don your reds and head back to town. Ignore the idea that they are pink pants. They are ”reds.” Durable, comfortable, and 100% cotton, they’ll last you a long time. Just remember to wash them separately the first time, or you’ll risk a fully pink wardrobe.
When my family and I are looking to have an outstanding meal with great service (and show off those reds), there is only one place to go: 21 Federal. The restaurant is located in a house that is over 150 years old, and the American fare is good enough to be served at most tony New York digs. The yellowfin tuna with fingerling potatoes was just the thing to help get us through our last night on the island. Just remember that the kitchen stops serving at 9:30pm, and the restaurant is closed through the winter until June. Not that you’re likely to be on island before then.
While it’s always sad to leave the Grey Lady—and all her fantastic cooking—I know she’s been around for a long time and will still be there next August. To ensure a safe and happy return, toss a penny overboard as you round Brant Point.