Destinations
NANTUCKET
If you asked me to name my favorite places in the whole world, Nantucket would surely be near the very top of that list. Boasting 82 miles of pristine shoreline (and the highest concentration of pre-Civil War homes in the U.S., by the way), this tiny little island is an American postcard come to life. There’s something for everyone here – beautiful beaches, delicious restaurants, miles of bike paths to be explored… And even though summer is prime time for visitors, Nantucket is a magical place year-round. (Truth: fall is actually my favorite time to go.)
Here, a guide with all my favorites – from where to stay and what to do, to the best shops and can’t-miss restaurants.
WHERE TO STAY
THE WHITE ELEPHANT
This hotel is one that checks all the boxes: lovely accommodations, great service, and delicious food. The location is top-notch, too, sitting right along the harbor and a quick walk to Main Street. They offer a variety of accommodations, including suites and guest cottages. On my most recent trip, I stayed in one of the hotel’s “residences.” It was a two-bedroom suite with it’s own kitchen and living area, making it an ideal stay for a family or a group of friends.
GREYDON HOUSE
Designed by Roman and Williams, this hotel is chic and super cozy. The moody interiors beckon for a cocktail by the fire. Even if you are staying elsewhere, this is a great spot to stop for a drink after dinner or linger over an afternoon of Gin Rummy.
AIRBNB
While I enjoy all of the amenities that come with a hotel stay, I’m a big fan of renting a house on Nantucket. The homes on this island are idyllic – think: brown-shingled cottages surrounded by white picket fences and cobblestone streets. Whether you’re looking for something close to town or perhaps beach proximity is most important, there are so many great options (this one looks divine for a large group!) from which to choose. Word to the wise: the really good ones go fast!
WHERE TO EAT
STRAIGHT WHARF RESTAURANT
Located right along the harbor, this 45-year-old restaurant is a consistent favorite. The vibe is warm and elegant, and the menu is full of delicious and fresh seafood.
THE CHANTICLEER
There’s something so magical about this place. Whether you go for lunch or dinner, it’s impossible not to find this place utterly charming. I have yet to find something I don’t like on the menu. My personal favorite? The burger.
SOMETHING NATURAL
One of my favorite things to do is stop by this sandwich place on my way to the beach. Their sandwiches are the best on the island (I love the BLT) and the bread is outstanding. Don’t forget to snag one of their famous chocolate chip cookies on your way out.
CRU
There’s no shortage of Nantucket restaurants with oysters on their menu, but it’s my personal opinion that this where you’ll find the best ones on the island. Whether you go for lunch (order the lobster salad) or dinner, this place always feels like a party.
VENTUNO
Located just off of Main Street, this charming restaurant features a seafood-centric Italian menu. The fish is always fresh and the homemade pastas are delightful.
LOLA 41
With a menu that ranges in offerings from sushi to burgers, this restaurant really does have something for everyone. Open for dinner only, it has a great vibe that’s perfect for a casual, but festive and special meal (think: dinner with your girlfriends or a date night!). The cocktail list is equally impressive so be sure to look that over before you start thinking about which sushi rolls to order.
other favorites…
American Seasons, Topper’s, Galley Beach, Millie’s, The Nautilus, Lemon Press, The Club Car, and Óran Mór.
WHAT TO DO
ENJOY HAPPY HOUR ON THE WATER
Hop on a boat and explore the island from the water! Shearwater Excursions offers several different boating experiences (from whaling history tours to kids fishing trips) for groups, or you can book your own private charter. If you’re there with a group of friends or family, charter the boat for a cocktail cruise and BYOB.
VINTAGE SWEATER (SIMILAR STYLE) • JEANS
SPEND A DAY AT THE BEACH
Don’t let the size of this tiny island fool you: there’s no shortage of great beaches. Selecting which one to spend your day on all depends on the vibe you want. In the mood for a party? Check out Surfside or Nobadeer. Prefer a quiet scene primed for a picnic? Head to Madaket Beach on the far Western end of the island. If you’ve always wanted to try surfing, head straight to Cisco.
BARTLETT’S FARM
This family-owned farm sells fresh produce and has one of the most outstanding flower selections on the island. If you’re staying in a house, consider this your grocery store. It’s a favorite of locals and visitors alike.
NANTUCKET LIGHTSHIP BASKET COLLECTION
If you’re not familiar with a Nantucket basket bag, you surely will be after a few days on island. The distinctive handbags originated over 150 years ago, first constructed by crewman of lightship vessels as a way to pass the time at sea. Now, at The Whaling Museum, you can view an extensive collection of these incredible bags. Tip: Learn to weave your own basket by signing up for one of the workshops!
RENT A BIKE
There’s really no better way to get around Nantucket than by bike. With miles of paved bike paths, you can easily explore every inch of the island – and get a great a workout in while you’re at it! Most of the hotels offer bikes to guests free of charge, but if you’re staying in a private house then give Young’s a call and they’ll deliver the bikes directly to you.
YOUNG’S BICYCLE SHOP
DOUBLE SCOOP IT AT THE JUICE BAR
No trip to Nantucket is complete without a visit to The Juice Bar. The ice cream joint is famous for their homemade flavors and waffle cones. In the evenings (and sometimes post-lunch hours!), the line wraps around the block. Don’t let that deter you. It’s well worth the wait.
WHERE TO SHOP
DRESS // SUNGLASSES // BAG
GYPSY
Located on Federal Street, this beloved boutique stocks a unique edit of high-end designers – think: The Row, Lisa Yang, Chloé… Tip: If you’re visiting the island for a wedding and your bag gets lost along the way, this is the place to hit for a replacement dress.
SERENELLA
Stocking a mix of super cool – and colorful – brands like Thierry Colson and La DoubleJ, this boutique has a slightly bohemian edge that reminds me of a store you might wander into while in Italy. Equally as fabulous is the assortment of tabletop goods – think: a vibrant selection of dinnerware and linens from the likes of Emporio Sirenuse, Sensi Studio, and more.
ERICA WILSON
For anyone who has an interest in needlepoint, this is a required shopping destination. Though its grown to include a mix of women’s and children’s clothing, the needlework is still its shining star. You can find a variety of beautiful canvases to take home with you. P.S. If you happen to work quickly and finish the needlepoint while still on island, Erica Wilson will does offer finishing services.
SYLVIA ANTIQUES
This shop is always one of my first stops. It’s curated in such a way that it always feels full of special things without feeling overloaded (read: overwhelming). The shop specializes in nautical antiques, including ships figureheads, sailor-made art, antique ivory, and more. It’s also worth noting that they carry the largest selection of vintage Nantucket Lightship Baskets on the island.
LYNDA WILLAUER ANTIQUES
This antique store has been a Nantucket favorite for over 45 years. Specializing in English furniture, Chinese export porcelain, landscape paintings, and Majolica and Staffordshire pottery, this place is a treasure chest. But! The best part about this shop is the collection of vintage Czech Christmas trees. There’s an entire room dedicated to these magical sparkling trees that will blow you away. In fact, I loved them so much that I started a collection for myself.
WHAT TO PACK
First things first: leave your stilettos at home. Nantucket’s cobblestone streets aren’t friendly to heels, and you’ll be much happier if you fill your suitcase with a mix of flats, a pair of sneakers, and perhaps a pair of espadrilles. As for the rest of your packing list, you can keep it casual. If you’re headed there in the summer then white denim, loads of sundresses, and a light sweater should do the trick. The winters there are another story. You’ll need to bundle up so err on the side of layers (cozy sweaters and definitely a puffer) and don’t forget a pair of extra-warm boots like these.
DRESS • SHOES • VINTAGE NECKLACE
