Stepping onto Nantucket is like stepping into another world: a quaint island frozen in time, blooming with fresh hydrangeas, teaming with beautiful people, grey clapboard cottages, world class restaurants and picture-perfect beaches. Here’s your guide to navigating the island.
Nantucket's sumptuously slow pace of life is one of its main draws, and there's no better place to get on island time than at Harborview Nantucket. The darling cottages are clustered right along the water (hello, private beach!), and feature a variety of creature comforts: Cisco Brewer’s beer in the fridge, a roaring fireplace perfect for huddling around at night, and cozy robes to sip coffee in on your porch in the morning. The service is the real star, though; the rotating staff of concierges goes out of its way to accommodate your every request.
Escape the main town and head to sleepy Siasconset to meander through some of the oldest homes on the island. The crushed shell path winds around the quaintest cottages you could dream of—all with ocean views, over-the-top gardens, and friendly neighbors. Afterwards, walk down to the beach and settle in for an afternoon of sun and seal watching.
It’s no surprise that Nantucket is home to some of the best shopping on the East Coast. Designers and local artisans flock to the island in the summer, selling stunning selections of beachwear, flowy dresses, dainty jewelry, and massive straw totes. There are shops galore all throughout town, but keep an eye out for Milly & Grace and Salt, two of our favorite boutiques.
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For the true highlight of your trip, charter a boat through Nantucket Mermaids. Their founder, Leah Collins, knows just how to take care of every last detail– like your favorite Pinot Gris chilling and ready on board. There are a variety of yachts and sailboats to charter for a sunset dinner, a day in the sun, or a cocktail party, manned by captains and stewardesses from all over the world. We took out their new 55-foot-long Zeelander yacht, boasting multiple luxe sleeping quarters, a beautiful bar with a sunroof, and, naturally, a hidden warm shower spray on deck to warm you up after chilly dips in the Atlantic.
This won’t take much convincing: sit on Cru's dock lounge for lunch, order some “summer water” (what the locals call rosé), take in the views (of the fabulously dressed women, foreign yachts, or Cru’s impossibly fresh take on Nautical design– your call), and chow down on the best lobster roll you will ever taste. Be sure to come back at night– it’s a party.
For a low key-drinking experience, grab a ride out to Cisco Brewers (or hop on their shuttle in town). Whether you’re sipping Whale’s Tale Pale Ale or frozé, the best part is definitely grabbing grub from the various food trucks and raw bar parking in the beer yard. It’s a stay-for-hours kind of place.
Go to this sweet spot early in the day or in the late afternoon when everyone’s napping to avoid the lines that form for the crispiest, most delicious waffle cone you’ll ever taste. Choose from dozens of homemade flavors, and be sure to opt for the infamous rainbow sprinkle dip to get the perfect photo.
A Nantucket icon for a reason, The Boarding House is a classic dinner destination. Whether you’re dining al fresco or in the intimate underground dining room, it's the perfect spot for a romantic date or a dinner with friends. Order a round of spicy jalapeño martinis, take in the golden glow, and go for the housemade lemon lobster spaghetti. It will change you.