Nothing speaks ‘Summer’ to me like the island of Nantucket. It is hard NOT to fall in love this quintessential New England island, just 30 miles south of Cape Cod the minute you arrive. The minute you step off the plane at ACK or the ferry, and take in the salty, sea air, you just feel elaxed.
The grey cedar clap board houses, harbors and wharves, lighthouses, and hydrangea-lined cobblestone streets (leave your heels at home!) all create a sense of stepping back in time. What I love most about island is that not much changes. It is one of few Summer destinations that has resisted huge development, with no chain stores or even traffic lights to be found on the island.
Some of the best places to stay are the one of the iconic Nantucket Island resort properties which include Jared Coffin House, the White Elephant Hotel and Village near town, the White Elephant Lofts on Main Street or the more secluded, Relais & Chateaux The Wauwinet hotel.
Another wonderful new option is the utterly charming and stylish boutique hotel, the Greydon House located right in town.
In Sconset, pick up a sandwich pre-beach at the old-time Claudette’s Sandwich Shop. 10 Main Street, Siasconset.
Or’ The Whale: Located on Main Street, this new restaurant isfrom the owners who brought you the Sandbar at Jetties Beach and has been quickly embraced by locals and tourists alike. It was only open a week when we at here and we loved it. Highly recommend the clam chowder, lobster rolls and to-go daily fresh-baked donuts. 38 Main Street.
Sandbar at Jetties. A popular casual open-air restaurant right on the beach with a fun atmostphere. 3-5 p.m. it gets packed for $1 oysters and live music at sunset. A must. 4 Bathing Beach.
Galley Beach: Just down the road from Sandbar, this indoor/outdoor restaurant is also on the beach and more elegant (not for families with younger kids). This is the place to go around sunset and lounge outside for cocktails. Seafood, raw bar, burgers and dogs. 54 Jefferson Avenue.
Nautilus: Rustic-modern hotspot in town featuring global small plates and inventive cocktails with whimsical names (I recommend the Nauti Dog or Kermit the Frog). One of the best dinners I have had. Great ambiance and menu. They only take same-day reservations. Order the crispy duck and ribeye ahead. 12 Cambridge Street.
Lola 41: Located directly across White Elephant Village, this is another constant favorite of ours. Incredible cocktails, sushi and burgers are the best on the island as are the fries and Mac n’ cheese.
Via Mare: The only restaurant on my list that I didn’t get to try is this atmospheric Italian bistro in the new boutique hotel, Greydon Housein town. I did get a tour of the hotel and restaurant during our visit and this is the top of my list for my next trip back. The menu features crafty cocktails and wonderful Italian dishes
Boarding House: We loved this restaurant on Federal Street for its ambiance as well as farm-to-table organic and locally sourced menu. Make reservations well ahead as it is a popular spot for dinner.
Black Eyed Susan: This tiny (cash only) institution on India Street is known for its diner-style breakfasts. Go early or prepare to wait in line. Get the counter if you can.
Brant Point Grill: Located at the White Elephant Hotel, this is a must-do for Sunday brunch or cocktails at sunset. Get the Bloody Mary!
Lola Burger: Located a little outside of town, this super casual offshoot of the popular eatery Lola 41 serves excellent burger and craft beers
Cisco Brewers: A complimentary van from the visitors center in town provides a continuous loop to the island’s only brewery where local bands play all day, and every type of craft beer and ale on tap (wine is served too) imaginable is there for the tasting at three different bars. Food trucks feature everything from oysters and lobster rolls to dumplings and tacos. Go for lunch or cocktail hour on a nice day. Tours also available daily.
Cru: A chic and stylish nautical eatery the end of the wharf. Go for dinner and order the oysters and famous Lobster Rolls which has deserved reputation as the best Lobster Roll on the island
The Pearl: for Asian-inspired seafood on Federal Street.
Mitchells Book Corner: Our favorite bookstore in Nantucket. Very old-school, independent bookstore with local authors. 54 Main Street.
The shops below are ideal for shopping with your teen or tween:
Peter Beaton Hat Studio: Just beautiful and customized straw hats and totes. 16 Federal Street.
Skinny Dip: Another great teen clothing spot. Great swimsuits. 23 Old South Wharf.
Cattivo: Inexpensive, cute outfits for teens. 20 Center Street.
Jack Wills: British store offering preppy classics with a trendy twist. One of only two boutiques in the States. 1 South Water Street.
Vineyard Vines: Classic preppy clothing, always find something I love here. 2 Straight Wharf.
Res Ispa: Next to Salt boutique, this store has great jeans, sneakers, and unique clothing. Your teen will love it. 4 S. Water Street.
Perch: Clothing store on the harbor. Last Summer, they did a pop-up with Veronica Beach. 2 Harbor Square.
Salt: 4 South Water Street.
Goop MRKT pop up: Pretty store sparingly filled with expensive apothecary items but like the ones I visited in Brentwood and Montecito, I never find anything I want to buy. 22 Center Street.
Rent a jeep for the day and explore the island.
Get an ice cream at either of both of these institutions. You can expect lines at both for their amazing homemade ice creams: Jack & Charlies: Located on the wharf and Juice Bar: On the edge of town, conveniently close to the White Elephant Village. 12 Broad Street.
Bring your kid to Force Five Surf . A local tipped us about the sneaky back room of this surf shop on Union Street that is full of every candy you can imagine. Bring cash to the boy with a tin box to pay for your candy. Then get some bathing suits in the store.
Don’t miss Sunday Brunch alfresco at Brant Point Grille at the White Elephant.
Visit the charming town of Siasconset, a 15-minute taxi (or Uber) ride from the Village. You will bump into artists painting on easels alongside the tiny bungalows dotting the hills to the sea. Pick up a sandwich at Claudette’s and take a blanket to the beach (my favorite one on the island). Stop at Sankaty Lighthouse on the way back.
Hang at any of the many beaches. Children Beach is across from the White Elephant Village but we liked Jetties (a 5 minute bike ride or quick van shuttle away) better, especially as Sandbar restaurant is there.
On a rainy day, the Whaling Museum in town is always interesting with interactive exhibits.