We love to travel and pride ourselves on visiting new destinations, but Nantucket is one place that we return to year after year. We’ve affectionately nicknamed Nantucket our “happy place,” as this idyllic island located 30 miles off the coast of Cape Cod is truly special. Its quaint historic homes, miles of untouched natural beauty, and pristine beaches coupled with its fantastic shopping and dining scene make Nantucket an excellent choice for a summer getaway.
We’ve been regularly visiting the island for the last 12 years and over time, have created our own “must do, see, and eat” list for our visits. These are the places and activities that I look forward to experiencing year after year! I am often asked for recommendations for Nantucket so I wanted to create a comprehensive guide that rounded up all of my favorite things to do and see on the “Grey Lady.”
The A-Lyst Ultimate Guide for Nantucket
You can’t visit Nantucket without spending a day at the beach! All of the beaches on Nantucket are gorgeous and for the most part, you can find a stretch of sand that isn’t too crowded. There are so many beaches that you can easily go to a new beach each day of our trip!
Located on the south shore of Nantucket, Ladies Beach offers excellent waves and an escape from the crowds. I’d suggest picking up a sandwich and snacks at Bartlett’s Farm before spending a day here. To get to the beach you need to drive down a an unpaved pathway, but a four wheel drive vehicle is not necessary.
Steps Beach wins the award for the most dramatic walk to a beach! Frequently captured in photographs and paintings, the staircase descent to this north shore beach is simply stunning. If you want an Instagram-worthy photo, this is the place to go!
If you love hunting for shells, look no further than Washing Pond Beach. We’ve found so many amazing conch shells here over the years and it’s so fun to walk the beach and see what you’ll discover!
If you’re in a Jeep, you have to visit 40th Pole. Unlike heading out to Great Point, you don’t need to deflate your tires to get on the beach here, which makes this a great option for easy off-roading. Don’t get me wrong, it’s definitely a bumpy, rugged drive, but that’s part of the fun! Bring a cooler and all the necessary supplies and set up a beach tailgate here for the day.
Cisco Beach and Surfside Beach
On a quest to ride some waves? All of the beaches on the south shore are a surfer’s delight. We came to both Cisco and Surfside after a recent hurricane had passed by the Island and have never seen a bigger surf!
If you’re an early riser, head to ‘Sconset for the sunrise and maybe some seal watching, too! Located on the eastern end of the Island, Sconset Beach is wide and expansive, and if you move away from the lifeguard area, it’s relatively quiet. We love bringing Walter to the more remote part of the beach to play.
Deflate your tires by The Wauwinet and head out to the northernmost point of Nantucket to watch the sun go down. On a warm summer night, it’s a blast to go off-roading out to Great Point Lighthouse and set up a picnic on the beach.
There are so many wonderful small businesses on Nantucket! I love spending a day (or two!) strolling through town, popping in and out of all of the boutiques. Whether you’re hunting for a new summer outfit, the perfect memento, artwork, or beach chic homewares, there’s something for everyone.
This is by far my favorite boutique on Nantucket. The owner, Julie, has a keen eye for gorgeous, one-of-a-kind styles and features interesting designers that you don’t see in any other boutiques on the Island. I have so many gorgeous dresses from The Lovely and when I wear them, I always get compliments!
If you’re a fan of needlepoint, you need to visit Erica Wilson while you’re in town. Beyond featuring designers like Cara Cara and Poupette St. Barth, the boutique also offers apparel designed by Erica Wilson, including pieces that are in collaboration with brands like Roller Rabbit.
Murray’s, the creator of Nantucket Reds, is an Island classic! Its rich Nantucket history paired with its vast selection of men, women and children’s apparel make this a must-visit when on the Island. My husband has found so many great pieces here over the years, ranging from well-fitting blazers made exclusively for Murray’s to classic “Nantucket Reds” separates.
Also check out: Milly + Grace, Grace Geier, Erin Hielle, and Blue Beetle.
A Nantucket staple for over 40 years, Freedman’s has the most unique collection of stately homewares including clocks, lighting fixtures, and furniture. We love popping in here to browse all of the interesting pieces.
This is the kind of store that makes me want to redesign our entire condo to be island chic! From flatware to linens and everything in between, Nomad is just dreamy.
This boutique features the prettiest kitchen tools and accessories paired with unique jewelry, clothing, and gifts. I enjoy ogling over their beautiful selection of glassware, cocktail accessories, and place settings.
Nantucket has a very rich and vast artist community. You could spend an entire day just exploring the art galleries on the Island!
Specializing in American Impressionism,Pierce Galleries features the work of Zhen-Huan Lu. We always stop by to admire his paintings.
Known for his fine art photography, Nathan Coe just relocated the gallery, which features his work alongside others, to a new space on Main Street.
Featuring a mix of contemporary and traditional art, I love viewing the gallery’s large collection of Hunt Slonem bunnies.
The food scene on Nantucket is very impressive, but be forewarned, you have to book your dinner reservations well in advance. Each spot has a different method for reserving a table, so I’d refer to their website for more information, but many are on Resy.com or OpenTable.com. You can’t go wrong anywhere you choose to dine!
Two words. Morning Bun! The most deliciously sweet cinnamon sugar goodness. Be prepared, they go fast, so it feels like quite the conquest when you actually get your hands on one.
A fixture in mid-island for decades, this cash-only eatery features amazing donuts and breakfast fare. The classic sugar-coated or coconut donut is the way to go!
Expect a wait, but it moves fast! This homey restaurant features breakfast staples like pancakes and scrambles.
This mid-island restaurant offers an expansive menu of both healthy and indulgent breakfast items. I love sitting on their patio!
There are so many good things on this menu, including fresh smoothies, but I always opt for one of their yummy salads or bowls!
Part food truck – part market, 167 Raw is a casual favorite — its patio is also dog-friendly, which is a plus. Don’t miss their fried oysters!
Located on Old South Wharf, this sushi spot has an adorable patio that sits between shops along a shell-lined pathway. I always get the build-your-own poke salad bowl!
This is a laid-back, toes-in-sand kind of spot that’s perfect for lunch or an early dinner. I’m obsessed with their frozen drinks, especially the BBC. Pro tip: they offer a buck-a-shuck with oysters and clams from 3:00 p.m. – 5:00 p.m.!
For more of an upscale lunch option, the Brant Point Grill at the White Elephant offers a lovely view of the water and delicious food.
If you’re coming from town, stop by Something Natural and pick up delicious overstuffed sandwiches, gooey cookies, and homemade iced teas for your day at the beach. Pro tip: order a “half” sandwich at Something Natural because they are huge!
Grab + Go:
Claudette’s (sandwich shop in heart of ‘Sconset village – it’s a bit overpriced for simple sandwiches, but consistently good), Something Natural (already mentioned above and should not be missed), Fresh (convenient location in town with delicious sandwich options and alcohol), and Provisions (hidden behind the Gazebo on Straight Wharf, this is another spot for hand-crafted sandwiches).
This is a bold statement, but I think The Chanticleer is my favorite restaurant on the island. On a summer night, this restaurant is simply magical. Originally founded as an ice cream shop and tea room by a Broadway actress in the early 1900s, The Chanticleer is a true Siasconset mainstay. From the ambiance to the food to the service, I adore everything about it! Pro tip: Ask to be seated in the front garden and you will not be disappointed.
Set right on Nantucket Harbor, Cru’s patio allows you to enjoy an al fresco meal with a side of yacht watching. The raw bar, smoked fish dip, and warm, buttered lobster roll are menu stand-outs, and don’t miss sipping the Cru-comber, the most refreshing cocktail! I also recommend checking out the inside bar for drinks and mingling – it has an amazing vibe!
If you’re in the mood for delicious Italian cuisine, run don’t walk to Ventuno. I love the polpette and spaghetti alle vongole for food. They also make one of my favorite espresso martinis!
This is a recent addition to my list, but our meal there during our last trip was one of our favorites. We were delighted by the distinctive, unexpected flavors. The calamari and halibut were outstanding.
Straight Wharf is an Island staple leaning on local purveyors to create their menu of fresh seafoods and meat. Pro tip: Request a table on their back patio so you can look out on the water and watch the ferries come in and out!
Husband and wife team Michael and Orla LaScola consistently serve up innovative globally-inspired cuisine at this India Street restaurant. Their food plating *almost* makes dishes too pretty to eat! We love sitting on their dreamy patio or grabbing a seat inside at their dimly lit bar.
It took us way too long to try Oran Mor for the first time, but once we did, we could see why it’s been a mainstay on Island for over 25 years. This upstairs eatery is incredibly cozy (…the kind of atmosphere you crave on a cool summer night) and the food is absolutely delicious. Unique flavors blend together across Oran Mor’s eclectic menu featuring pastas, meats, and fish, and you’ll find yourself saying, “wow” more than once!
Get the whole roasted peking duck, you won’t be disappointed! This is an intimate, buzzy spot that serves up the delicious tapas alongside fantastic cocktails!
While Lola has expanded with locations in Boston and Palm Beach, I still adore the quaintness of the original Nantucket location. The playlist here is always on fire and I love sitting at the bar to eat and drink.
Featuring amazing homemade ice cream and the longest line you’ve ever seen! I love the Juice Bar and feel that it always lives up to its hype. For me, a trip to Nantucket isn’t complete without enjoying a freshly made waffle cone (or cup!) overflowing with one of the Juice Bar’s rich, creamy flavors!
The Counter at Nantucket Pharmacy
Reminiscent of an old-fashioned soda fountain, the ice cream counter inside Nantucket Pharmacy on Main Street is worth a visit. Island Kitchen recently began serving their homemade ice cream there and the line to get a cone is much less intimidating than the aforementioned Juice Bar. The flavors rotate, but I love Island Kitchen’s C is for Cookie!
For sunset lovers, there are so many beautiful vantage points that you can enjoy on the Island. I relish in the sunsets on Nantucket and love going to a new spot to watch them each night of our vacation.
The lawn at The Wauwinet offers a breathtaking view for sunset. This Relais & Chateâux property located at the more secluded northeast part of the island is home to TOPPERS, where you can also enjoy a delicious dinner. Pro tip: The Wauwinet Lady is a complimentary boat shuttle between sister properties, The White Elephant and The Wauwinet. I highly recommend booking the one-hour trip to/from dinner. It’s so fun to be on the water and the boat ride home offers stargazing that is truly out of this world!
I love Galley Beach so much that I have a whole blog post dedicated to enjoying a summer sunset there. Dress to impress and enjoy the sunset with your feet in the sand and a martini in your hand.
Pack a blanket and lawn chairs, order a pizza to-go from Pizzeria Gemelle, and head out to Jetties Beach (walk past the Sand Bar to the public beach area) to watch the sun go down! Note: we snagged a table at the Sand Bar to eat our pizza because it was closed due to an earlier storm; you can’t bring outside food there on a normal day.
Head to the unassuming area of Madaket, located on the western end of the Island, to enjoy a sunset. We typically put our name in at Millie’s and then head to the beach to watch the sun go down as we wait for a table. Millie’s is one of my favorite laid-back spots and it’s equally great for lunch and dinner. Get the guacamole and chips and try one of the eatery’s tacos (I get Smith Point every single time) or quesadillas (Steps Beach is so good!) paired with a margarita.
Walk the Bluff Walk and Explore Siasconset
Siasconset, abbreviated to ‘Sconset, is my favorite part of the Island. Founded as a fishing village, this quaint town is home to dozens of 18th century cottages that are complemented with crawling roses and gorgeous gardens. In early July, the village of ‘Sconset looks like something out of a storybook because everything is in bloom! After exploring the rose-covered cottages, make your way over the Bluff Walk. This walking path takes you alongside the bluff of the east shore where you’ll meander past stunning seaside homes and take in unparalleled views of the Atlantic. Unfortunately, the trail has been cut short over the years due to an ongoing erosion problem, so if you want to walk to Sankaty Head Light, you can continue on your stroll via Baxter Road.
Spend the Day at Cisco Brewery
Get there early (trust me, the line becomes long!), snag a table, bring your pooch, and order Figawi Wowies! Cisco Brewery is a great place to spend an afternoon. There are plenty of food trucks, beer, wine, and cocktails, and live music — plus it’s one of the best dog-friendly spots on the Island.
Nantucket is filled with bike paths that offer a chance to take in scenic views as you explore the Island. There are bike paths to take you all over the Island, including to ‘Sconset, Madaket, and beaches like Surfside.
This is a great rainy day activity. If you’re curious about Nantucket’s whaling history, this museum offers an excellent overview that’s brought to life with a skeleton of a 46-foot sperm whale that washed ashore in 1998.
If you’re visiting Nantucket for a weekend and staying in town, I don’t necessarily recommend renting a car as many attractions are walkable. Alternatively, you can easily rent a bike (I’d suggest family-owned, Young’s Bicycle Shop) or take the WAVE bus, which is the Island’s public transportation. It’s very clean and easy to navigate, just make sure you have the exact fare of $2.00 or $3.00 when you board. You can also buy a multi-ride bus pass on board. There are taxis and UBERs on the Island, but the cost is incredibly inflated. For certain destinations, such as Cisco Brewery or The Wauwinet, there are also complimentary shuttles that can take you both and forth, which departs from the Visitor’s Center at 25 Federal Street.
If you’re staying outside of town, I do recommend having a car on the Island. The Steamship Authority runs several ferries a day that allow car reservations; however, these book up months in advance. Your best bet is to rent a car on the island via a local company or the app, Turo. We used Turo on our most recent trip to Nantucket and it worked out well!
Quaint, traditional inns make up the majority of Nantucket’s lodging, however, there are also several hotels, like The Nantucket, White Elephant, and The Wauwinet, that cater to families with larger rooms and more robust amenities.
For inns, the Union Street Inn, Jared Coffin House, and Brass Lantern are longtime standbys and well-appointed.
In recent years, there’s been a slew of more glamorous newcomers like Greydon House, Life House, Hotel Pippa, and Faraway that are also very appealing.
Most properties require a three to four night minimum stay during peak season, so if you want more flexibility or a longer term stay at a better nightly rate, booking a cottage rental on AirBnb and VRBO is the way to go.
The A-Lyst is a Boston-based lifestyle blog curating the very best of style, beauty, food, and travel.