17 Things To Do on the Northeast’s Most Charming Island

Nantucket Island

Ask anyone who's ever been to Nantucket, Massachusetts, and they'll probably tell you it has a special place in their heart (as a born-and-raised northshore Bostoner, it definitely has mine). Just an hourlong ferry ride from the Cape, the "Gray Lady" has become frequented by celebs, politicians, and one-percenters alike, but it hasn't lost its easy, lived-in charm (maybe it's thanks to the 400-year-old cobblestones, weathered gray-shingled houses and seventh-generation residents that stand unimpressed by the Patagonia-vest set.) I've gotten to visit numerous times—once to interview Queen of the Beach Read herself, Elin Hilderbrand, another on a press visit to see the then-new Nantucket Hotel, and then more than a few times on my own. Each time, I've received recommendations from islanders, hotel staff, tour guides, restaurant owners, and friends, and along with those, I have also compiled my own hit list of the best things to do in Nantucket, if you should be lucky enough to visit.

How do you get to Nantucket?

The easiest way to get to Nantucket is by high-speed ferry. You can book a one-way or roundtrip fare from Hyannis on Hy-Line Cruises. You can also get there via Seastreak ferry from New Bedford or even New York City. There are regularly scheduled flights on major carriers out of Nantucket Airport. Or if you've got a dog in tow (and can shell out big bucks) Tradewinds offers private and shared charters.

What is the best month for visiting Nantucket?

June, July and August are high season. Weather temperatures peak at the 70s or 80s, and the fog mostly burns off as the sun's rays beam through any clouds. However, you'll still be met with the occasional cold front or sprinkles, so bring layers. "Sweater seasons" May and September may be my favorite time of year to visit as crowds thin, making it easier to get ferry seats, restaurant reservations, and a spot on the beach. Even at the start of September, the weather stays sunny and in the 70s.

1. Get a good spot on the ferry

If you're traveling with kids or dogs or both, you may want to try to line up early to secure either a spot inside at tables, or up on the first-floor deck (if you so choose.) While it's windy, many prefer the deck for the ocean breezes and first-rate views of Cape Cod, the Atlantic, and the first views of Nantucket. If you're on the 7:05 p.m. ferry, the "golden hour" sunsets can't be beat.

2. Decide where to stay

Nantucket has an array of beautiful, impeccable small boutique hotels in town, plus options in 'Sconset and Madaket, but you'll want to plan far ahead since they often sell out and prices top $1,000/night and upwards in the summer months. Some of the most popular are The White Elephant, newly redesigned Cottages at Nantucket Boat Basin, and, right now, Wes-Anderson-esque The Faraway (people do drinks on the Sister Ship patio to get the vibes). Same with AirBnBs—plan far ahead. I got to stay at the Nantucket Hotel + Resort on a press visit once, and I'd choose it above all. Easily walkable from town, the rooms were spacious, airy, and coastal-inspired (and some even dog-friendly!) The property has two fun pools, fitness classes, a shuttle service, its own tall ship tours, and more. Elin Hildebrand hosts her famous book retreats here!

3. Stroll downtown

Quaint cobblestone streets greet you upon disembarking at the wharf. The walk to Main Street features jewelry shops, fudge (Aunt Leah's award-winning penuche is a must-try), and plenty of Nantucket gear (even for your pup!) Further down, you'll find preppy boho-inspired boutiques such as Milly & Grace, Nantucket classics Lily Pulitzer and Vineyard Vines and just-opened For Now. For exquisite home finds see Nomad.

4. Learn some history

The Whaling Museum is more than a local history museum—it's an experience. "Life Aboard a Whaleship" vividly retells what the whaling trade was like in the early 1800s, and the costs of the whale oil trade will never leave you. Other must-see exhibits include the sinking of the whaleship Essex, which inspired Herman Melville's Moby Dick, a restored 1847 candle factory, and even a 46-foot sperm whale skeleton.

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5. Check out an art gallery

Nantucket has long been known for its artist community, and a walk down Main Street will lead you to art galleries featuring everything from classic sea oils to modern art. Quidley & Company has collected works from emerging painters, installation artists, and collage artists, including Jojo Anavim's pop art collages and BREAKFAST's super-imaginative kinetic flip discs that follow your movement. So cool!

6. Spend time at the bookstore

What's a beach vacation without a juicy beach read? When in Nantucket, you must start with one from Queen of the Beach Read herself and famous islander Elin Hilderbrand. She's been known to make stop-ins to sign her latest novels at Nantucket institution Mitchell's Book Corner. Her last novel, Swan Song, is out this June (sniff, sniff) and she'll be making the rounds for talks on June 26.

7. Hit the beach—and the beach bar

Jetties Beach is one of the most popular for many reasons, namely its convenient, close-to-downtown location (easily walkable in 15 minutes, or you can grab a bus at the Whaling Museum or even a new NanTukTuk), it requires no long hikes up and down dunes to get there and boasts all-day Sand Bar at Jetties Beach for island vibes incarnate. Don't miss summertime frosé and buck-a-shuck oysters from 3 to 5 p.m.!

8. Bike around the island

Biking is one of the most fun ways to explore the island. You can rent a bike or scooter at Nantucket Bike Shop (you can just walk up and rent a bike for about $50 a day). The 1 to 2-hour trip to Cisco Brewery and Bartlett's Farm is a popular one, but if you've got half a day, you can take Polpis Road to Siasconset ('Sconsit) for views of the climbing rose-covered cottages and beach bluffs, and take photos at Sankaty Head Lighthouse.

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9. Have a pint—or three

Cisco Brewery is notorious for its afternoon party scene—enjoy live music while sipping a large selection of craft brews, including its famous Whale's Tale Pale Ale. If crowds are already lining up, you can also head to Nantucket Vineyard and Triple Eight Distillery, also on Bartlett Farm Road. Don't forget to try a "Figawi Wowie" — a blueberry vodka lemonade named after the famous Memorial Day sailing race.

10. Visit a lighthouse—or three

For that classic coastal New England Instagram shot, you're going to want to visit one of the lighthouses on the island. Brant Point Light House, closest to downtown and visible by ferry, is stunning, especially at sunset, as is Sankaty Head Lighthouse. The most hard to reach, Great Point Lighthouse is only accessible by Jeep or foot over 7 miles of sand (and you've got to know what you're doing since you can quickly sink!)

11. Take a tour

Beyond the shops, the beaches and beautiful scenery, Nantucket has a deep and rich history going back to colonial times—and long before. Gail's Tours' 2-hour minivan excursions offer a good overview of the island from a seventh-generation native. Nantucket Island Tour's Westender Tour takes you further afield, including the beautiful beaches at Madaket. Nantucket by Water has adult-bevy sunset cruises.

12. Walk the Bluff

If you've got time on the island, the 'Sconset Bluff Walk is def worth some space on your camera roll. Starting at Front Street, you can meander down the narrow footpath past gray-shingled cottages with flowering shrubs (it's especially pretty during hydrangea-peeping season!) It's about two miles long, so grab a canned beverage or two, a sandwich from Claudette's, and have a picnic at Sankety Head Beach.

13. Have a sandwich

Everyone loves The Lemon Press for the freshest smoothies, salads, and grain bowls, but my all-time favorite is a curried chicken salad sandwich or B.L.T. from Provisions when you're fresh off the ferry. PR maven Courtney Dwyer, who reps the Nantucket Food & Wine Fest, recommends Fresh Nantucket: "Literally the best sandwiches on the island—the Island Mambo is to die for. Pro tip: go to Fresh, then head to Steps Beach."

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14. Have a cone

The best ice cream on the island is also controversial. The Juice Bar reigns supreme, with lines down the block each night to prove it. They've got 40 flavors of homemade ice cream from Cookie Dough to Crantucket, plus fun new creations like Cookie Monster each day. But for slow-churned fans, Jack and Charlie's maple walnut on the walk to the ferry is perfect and you can lick while you wait.

15. Try some sushi or shellfish

Lola 41 is notoriously the best sushi spot on the island (and also my favorite.) Cru, right on the wharf, is "iconic" says Dwyer, and the place to see or be seen. (If you can get a reservation, champagne and oysters are divine.) Helmed by Chef Gabriel Frasca and Kevin Burleson of Clam Shack, Straight Wharf Fish Market is another recent opening and a quintessential, down-to-earth lobster roll shop with rave reviews.

16. Or some upscale coastal eats

The Pearl and Boarding House, locally loved Nantucket fine dining institutions, were forced to go dormant after the pandemic but reopened under new management for the 2023 season, and thankfully their legacy lives on (see menu favorites like wok-fried lobster and tuna martini.) Millie's in Madaket has glorious ocean views at sunset and delicious Baha-style fare. Make reservations (or try the new Millie's at the Rotary!)

17. Sing at a piano bar or to a live band

The Chicken Box will sound familiar if you're a fan of Hilderbrand's beach reads. "Nantucket isn't necessarily known for its nightlife but this one spot is the go-to on the island!" says Dwyer. "They often have the best cover bands (i.e., the Joshua Tree)—I swear I thought U2 was really playing, but they also get big acts too, like The Revivalists." Piano sing-a-long bar The Club Car is also iconic for Hilderbrand fans.

Next up: 17 Things to Do in Brewster, Massachusetts: The Cape Cod Town That's Full of Coastal Charm