“It’s hard to visit Nantucket in the summer and not fall in love with the place.”
When I first read this sentence that begins Peter Gott’s photography book Summer Windows of ‘Sconset, I felt that it couldn’t describe Nantucket any better. The island of Nantucket, Massachusetts, which is just a 30-minute flight (or a 1.5-hour ferry ride) from the coast of Boston has charm on every corner, almost 400 years’ worth of rich American history, and so much to offer as a summer vacation destination. This New England treasure was founded in 1641 as a shipping and whaling town, and today it attracts flocks of travelers from all over the world to enjoy its harbors, beaches and quaint town attractions in the summertime.
Cottages along the Nantucket Harbor
Now that we’ve got the history of Nantucket behind us, let’s dive into the fun part: What to do, see, eat and more! After visiting Nantucket twice this summer (I’m telling you, the love affair is real… Even our editor-in-chief Lauren has been bitten by the ACK bug!), I decided to put together a comprehensive guide to help you plan your next trip to this charming East Coast island. From the hydrangea-lined streets of ‘Sconset, to the shingled homes on Cliff Road, to the buzzing restaurants and bars in town, this guide covers all the basics and then some. If you’re looking to visit a place you will want to return to again and again, then be sure to bookmark this post (or Pin the photos below to your Pinterest travel board) and revisit it when you’re planning your next summer vacation…
Where to Stay…
Expansive grass lawn at Harborview Nantucket
Just a few blocks from the center of town, but tucked away on its very own private harbor beach, Harborview Nantucket perfectly blends being in the action, yet also being relaxing. The grounds boast 11 private and spacious guest residences, all of which are decorated beautifully, have waterfront views, and every amenity you could imagine (each unit has a full kitchen and washers and dryers). Pop open a bottle of complementary Cisco Brewery beer that comes in your room and take it down to the Adirondack chairs on the gorgeous grassy lawn at sunset for a pinch-me Nantucket moment.
Blue tiled shower at Greydon House
Known as Nantucket’s “newcomer hotel,” this boutique hotel has 18 immaculately decorated rooms and suites that epitomize the island’s nautical style and charming sophistication. Don’t miss the blue and white tiled showers, the fabulously cozy-yet-chic bar, or Chef Marcus Gleadow-Ware’s restaurant within the hotel (order the beef carpaccio to start, the diver scallops as your main, and the lemon meringue for dessert).
In mid-July, White Elephant will make your jaw drop with their lawn of hundreds of blooming hydrangeas in every possible color. Aside from their landscaping, this hotel has much to offer—from their harbor views, to their convenient location close to town, to their restaurants and spa. Come here for a romantic weekend with your special someone or a trip with the entire family—you’re guaranteed to have a good time either way.
One of few hotels located in ‘Sconset, the quieter west end of the island, Summer House puts their guests right on the beach with a fabulous restaurant and pool on the property to boot. The piano bar on the beach provides nightly entertainment with the sound of waves crashing in the background. During the day, camp out under one of the umbrellas at the beach or take a neighborhood walk through the charming surrounding neighborhood. Just don’t forget your camera—chances are you will want to capture every moment you see.
Where to Dine…
Double scoops in Juice Bar’s famous waffle cone
This waterfront hot spot in town sits right on the dock overlooking the boat basin and boasts one of the best lobster rolls in town (which is saying something in Nantucket). Come here with friends for a rosé weekend brunch or on date night for chilled oysters from the raw bar.
Heading to the island to celebrate a special occasion? You’ll want to call ahead to make a reservation at Galley Beach, like ASAP. This breathtaking restaurant originally started as a clam shack on Cliffside Beach, and has now evolved into one of the premier restaurants in New England. Here you can sip on champagne and eat truffle butter filet mignon with your toes in the sand at your beachside table. The view at sunset is nothing short of spectacular… And you just might get lucky enough dine here on a night when the fireworks go off.
Take a 180-degree turn out of ‘Sconset and head out to the east side of Nantucket that’s known for its booming fishing scene, and you’ll eventually find yourself at a favorite spot of the island locals called Millie’s. This relaxed, beachside restaurant and bar serves up a Baja-style menu that focuses on fresh, local seafood (which was most likely caught a few miles out front that day), and their signature cocktail, the Madaket Mystery. Come on a weekend night to enjoy the live music.
The Lobster Trap
This iconic island staple is one of the few family-owned and operated restaurants on Nantucket. The seafood is fresh, the lobster roll is divine, and the live bluegrass music on Sunday and Tuesday nights makes for an all-around great time. Casual attire and good vibes are all you need.
Lola serves up one of the best burgers in town, and a mean batch of truffle fries. With its outdoor picnic tables and relaxed vibe, this restaurant is a great spot for a casual bite, and perfect for bringing the kiddos along too.
The best spot for ice cream on the island. The flavors are good and the homemade waffle cones are even better. Be ready to wait in the line that wraps all the way around the corner during the summer months. It’s worth it.
What to Do…
Berry and cherry flavored frozen Sangria at Cisco Brewery
Have a frozen sangria at Cisco Brewery
One of my favorite ways to spend a Saturday or Sunday is by hopping on the free Cisco Brewery shuttle in town and heading out to the brewery. Enjoy beer, wine and whiskey tastings from local distilleries and vineyards while a live band plays music next to picnic tables. And it’s a good idea to come hungry… Local restaurants Millie’s and Lobster Trap have food trucks that serve up delicious fare. P.S. Don’t pass up the frozen sangria Nantucket Vineyard on a hot summer day here.
Sankaty Head Lighthouse at the end of the ‘Sconset Bluff trail
Bike ride from town to ‘Sconset then walk the ‘Sconset Bluff
If you want to burn a couple hours in the afternoon or have a beautiful morning run, I highly recommend renting bikes in town and riding the bike trail on Milestone Road all the way to ‘Sconset. The 8-mile trek will take you about 40 minutes, but it’s a great way to get active and moving. Then, pop into Claudette’s in the center of ‘Sconset’s little town for a bowl of their delicious chowder, and keep the activity going by taking a walk on the ‘Sconset Bluff trail. It will take you all the way to the Sankaty Head Lighthouse, which is a picturesque spot to relax for a while… Before starting the journey back!
Cruise the harbor with Endeavor Sailing
In my opinion, this is a Nantucket must. Grab a group of friends and call Endeavor Sailing to book an afternoon ride on the water. Captain Jim will fill you in on the history and geography of the island as you coast along, and I highly recommend you get on board with a chilled bottle of rosé if you’re sailing at happy hour.
Drive to Great Point Light
Within minutes of being on Nantucket, you’ll notice that the signature vehicle of the island is an older, charming Jeep (usually a roofless one in a fun, bright color). Make like a local and rent a Jeep for the day (they’re usually $20 a day from several rental places in town) and take a drive to Great Point Lighthouse. You’ll want to rent one with 4-wheel drive because part of the drive is on the sand. This lighthouse is harder to get to than others on the island, which makes it a special bucket list excursion to add to your itinerary. Don’t forget to pack a picnic with rosé and have lunch by the lifeguard tower.
Where to Beach…
Lifeguards on watch at ‘Sconset Beach
You truly can’t go wrong visiting any of these gorgeous Nantucket beaches. With their tall seagrass and winding wood paths, every one of them will give you the quintessential New England beach experience.
- Ladies Beach – Surf’s up! If you’re traveling with surfers, head to this beach when there’s swell. And dogs are welcome too—just remember to bring a leash.
- Jetties Beach – When you’ve had enough salt and sun, head to the restaurant and bar Sandbar at the top of the beach and order their fried lobster and summertime frosé.
- ‘Sconset Beach – Located just below Summer House, you can take a nap under one of their white umbrellas on this peaceful stretch of sand.
- Steps Beach – The picturesque view of wooden staircases that leads you down to the ocean is not to be missed.
Pristine white sand and umbrellas out front at Summer House
Where to Shop…
Candy-colored clothing on display at CJ Laing’s ‘Sconset boutique
- Milly & Grace – This cute boutique carries everything from Rebecca Taylor to Joie to hard-to-find Dragon Diffusion Bags.
- Salt Boutique – Run by a girl who grew up on Nantucket, Salt Boutique has a boho vibe and a range of must-have pieces that appeal to all age ranges.
- CJ Laing – This beautifully curated boutique will have you adding their straw bags and embroidered caftans to your wish list ASAP. They have locations in town and in ‘Sconset, so you can shop on both sides of the island.
- Peter Beaton Hat Studio – Pop into this special Nantucket store for a Peter Beaton straw hat with a ribbon color of your choice. It will surely become your favorite summer accessory.
Rose-covered archway in ‘Sconset
I hope you enjoyed reading a bit about my newest favorite vacation destination! As you can see, there is a lot to be done on Nantucket, and this is just a starting point. Let me know if you have any favorite Nantucket spots you would add to this list too.
Where is your favorite summer destination?
And, what city guides would you like to see us do here on LaurenConrad.com next?