Dreaming of Travel: Nantucket

Published on August 19, 2020 - Updated on August 20, 2020

A place like no other, to know Nantucket is to love her.

This small but mighty island in Massachusetts offers gorgeous scenery, good eats, and an abundance of family fun. Thirty miles off the coast of Cape Cod, Nantucket is known for its gray, cedar-shingled homes, beautiful beaches, and unique island vibes. In the summer months, the population of the island grows to over five times its usual size, and for good reason. Summer in Nantucket offers a unique combination of high-end luxury, wide-open spaces, and small-town charm. 

Nantucket Town

Everything about Nantucket screams cozy, from the cobblestone streets dating back to the mid-1800s to the placards on historic streets and homes dotting the island. Perhaps its most charming feature of all is the fact that there is not even a single stoplight on the island. For families used to traversing cities and suburbs via car, the accessibility of Nantucket once you’ve arrived is a welcome change.

There’s plenty to see, do, and experience year-round on the island, but summer is by far a favorite time for tourists and locals alike. For that reason, summertime on Nantucket earns a high spot on happyly’s list of favorite vacation destinations. 

The Best Time to Visit

Summer. Though there are festivals on the island in the winter and springtime, the island is prone to unpredictable New England weather which makes these times of year tricky for vacationing. Summers on Nantucket typically range between the low 60s and high 80s, with the occasional rainy or gray day. She is known as the “Gray Lady” after all. As long as you’re willing to include a sweater or raincoat in your wardrobe, then you’ll love the wide variety of family fun that Nantucket has to offer. 

That said, many call September their favorite month on ACK (as is true in many beach communities). To start, the water still feels generally warmer than June or even July despite slightly cooler air temperatures. Also, the island is more quiet and serene, reservations are easier to come by, the vibe is blissful as the pace of summer slows down, and as an added bonus, prices plummet!

Getting There

Wharf Nantucket Island

Getting to the island is an adventure in itself. The most popular means of travel is via the Hy-line and Steamship Authority ferries from Hyannis. Both companies offer passenger-only ferries as well as car ferries, however, you are wise to book well in advance for travel during the summer months, especially if you’re hoping to bring your car to the island. If you’re traveling with little ones who require lots of gear, bringing your car over is the way to go. You can simply load up and drive right on to the ferry. Most of the home rentals on the island offer driveways or parking options as well. 

Nantucket also boasts a small, but beautiful airport with many of its flights coming via Cape Air following a quick connection at Boston Logan. While there are larger commercial flights, be advised that many of the Cape Air options are small aircrafts - in fact, less than ten people small - so if small planes aren’t your thing, plan accordingly.

Getting Around on Island

Experience Nantucket by Bike

Nantucket Inn Bike.jpeg

Whether you bring your own bike from home or choose to rent them on the island, biking on Nantucket is a great way to have some family fun and explore. For the more active family, biking is a great way to get to and from activities during your stay as well. Whether you bike to the beach, into town, or to a local restaurant for a bite to eat, there are well-marked trails all over Nantucket that help you navigate bike travel like a local. 

The island favorites for renting bikes for the whole family are the Nantucket Bike Shop and Young's Bicycle Shop. They both offer home delivery service. In addition to renting bikes of all shapes and sizes, they provide bike accessory rentals, including child seats and burley carts for the little ones. Nantucket is extremely biker friendly, and on any given day you’re sure to see dozens of bikers on the bike paths and main streets of the island with little ones in tow. 

Public Transportation

Public transportation on the island is wonderful. Nantucket’s public transportation system ‘The WAVE’ is supported by small buses that take passengers to and from stops all across the island

Where to Stay?

Keep in mind, Nantucket is an island, meaning a limited amount of options at a higher rate per night than your average travel destination spot. That being said, you can find great deals in local hot spots especially during the ‘offseason.’ We highly recommend considering a trip to Nantucket in the Spring or Fall as well if you are comfortable with the chillier weather!

Gate to the Beach Nantucket.png

In prime season summers, your best bet is a rental through Airbnb or VRBO. Both options are popular with island homeowners and have a wide variety of options from rooms in a house or inn to private homes and estates scattered across the island. If you’re looking for a less expensive option, cast a wide net. You’re more likely to steal a deal if you’re a bit of a drive from town. Keep in mind, even though the WAVE is a great resource, a car is more necessary in some areas to make the rest of the island accessible - calling for a car can be erratic and costly.

When renting through third parties, keep in mind that nightly pricing often does not include a cleaning or cancellation fee, so be sure to check out the details when considering options on an app or online. Some cancellation policies are strict, especially on ACK, so you’ll want to ensure you have the right level of flexibility if you need it. As an alternative, there are many knowledgeable agents on island familiar with the best rental options.

Probably the most popular places to stay on the island are The Wauwinet and The White Elephant. While pricey, they both offer amenities and features that would rival pristine hotels in big cities. Though it may be too over the top for a family trip, both are great options for a couples night out if you’re able to escape for a night, especially considering no children under twelve are invited to stay at The Wauwinet (though kids are welcome at The White Elephant).

Where to Play?

Favorite Family Activities 

Explore Downtown Nantucket 

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Downtown Nantucket is as beautiful as it is well appointed. From shops to restaurants, parks, harbor views, and beaches, Downtown Nantucket has something for even the pickiest ones in the family. We always recommend spending an afternoon wandering the little streets of town, popping into the local shops, and grabbing dinner by the wharf. (Insider tip: a personal shopping fave is Zero Main on Centre Street.)

Critter Cruise 

17 Straight Wharf

Check out Nantucket’s Critter Cruise, a one hour trip for kids where they go out on the ‘Monomoy’ to watch Captain Josh haul some fish traps and lobster gear, and then everybody gets to do some fishing. You never know what kind of creatures will come up in the traps so it’s quite the adventure for little ones. Once the critters are up on deck, they go into a "touch tank" so everyone has the opportunity to experience them up close and personal.

Sankaty Head Light

Sankaty Head Light Nantucket

Baxter Road, Siasconset (east end of Nantucket)

A bit further up from the end of the Sconset Bluff Walk is the Sankaty Head Lighthouse. Biking from Sconset to Sankaty Head Light is a great family-friendly activity on typically very quiet roads, making it an easy trip for families of all experience levels. It’s also a great walk or runs for those looking for something more challenging. The lighthouse sits on a large plot of land overlooking the ocean, with plenty of space for the kids to run around and explore. 

Cisco Brewers

5 Bartlett Farm Road

The perfect place to unwind after a long beach day, Cisco Brewers is great for families. Mom and dad can sample the island’s own brews and spirits, kids and adults can grab a delicious dinner and treats from the food trucks, and everyone enjoys live music with Bartlett's Farm and wildflowers as a backdrop on the massive outdoor patio. Dogs are even welcome! 

Sconset Bluff Walk 

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27 Bank Street

For older kids that enjoy the adventure of a good nature walk, the Sconset Bluff supplies a great hike along the cliffs overlooking the ocean in Sconset. The path takes you through yards, small wooded areas, and past some of the most beautiful views on the island. This route is not stroller or bike-friendly, as it is only a walking path so be sure to plan accordingly.  

Best Beaches

Nantucket Beach

North Shore

Children’s Beach 

Where: Off of Harbor View Way in town across from the Steamboat Wharf.

What: As the island’s mildest beach as the name suggests, Children’s Beach often features family-friendly activities like dance and yoga for kids and even a summer concert series. 

Who: Families - especially those with young children

Jetties Beach 

Where: 4 Bathing Beach Road. This one is an easy walk or bike ride from town, making it a prime spot for summer beachgoers. 

What: A relaxing family-friendly beach with plenty of activities for kids including volleyball nets, tennis courts, a playground, sailing and swimming lessons, tennis courts and a skate park. 

Who: Great for families with children, the water is shallow and very calm, there is a casual restaurant and changing rooms with showers making this one a great place to stop for the whole family. 

East Shore

Siasconset Beach

Siasconset Beach Nantucket

Where: Cod Fish Park Road

What: This is a charming little beach on the quiet side of the island in the town of Siasconset or Sconset as the locals call it. There is super limited parking and is a no-frills beach with only porta potties for amenities. Despite its lack of amenities, it is perfect for a couple of hours in the sand as it is often quiet and mostly frequented by nearby residents. It’s a great spot to catch the sunrise too. 

Who: Lots of locals out for strolls or sitting in the sun for a few hours. You may even see a seal or two sunbathing! This beach is also really close to the local hot spots Sconset Market and Sconset Cafe, both have great food and are close to picnic tables where you can stop and eat before heading home.

South Shore

Surfside Beach

Where: Located at the end of Surfside Road and accessible by a three-mile bike path or the island shuttle service with shuttles regularly leaving from town during the summer

What: This beach is great for families as it has onsite food and restroom facilities as well as a wide beach great for family picnics, games, and playing in the waves.

Who: This is one of the most popular beaches in Nantucket, so be prepared for larger crowds with locals and tourists of all ages.

Cisco Beach

Where: Hummock Pond Road 

What: This beach is not for the faint of heart. Popular among experienced surfers on the island, this beach is always packed with surfers after a big storm. The rip currents can be strong, so caution for anyone with an older crowd looking for more excitement. For the avid water fanatic, you can find one of Nantucket’s favorite surf schools operating from here as well.   

Who: Cisco has a loyal following of surfers and young adults looking for more excitement than the rest of the Nantucket beaches have to offer. This beach also has surfboards, wetsuits and stand-up paddleboards are available to rent. Conveniently located for all who want to end their beach day at Cisco Brewery!

West End

Madaket Beach

Madaket Beach Nantucket Island.jpeg

Where: The very end of Madaket Road, parking lot to the left.

What: A stretch of beach on the West End. Easily accessible from the parking lot, the beach boasts unrivaled sunsets and is close to the access point to drive out to Smith Point, which is an amazing option for families with SUV's. Don't forget to let a little air out of your tires if you decide to take your car out on the sand, but don't worry if you don't have a car, the WAVE stops just before Madaket Beach (at Millie's).

Who: Locals and Madaket summer residents who like to be a step away from crowds make their way to this beach. Madaket has a unique and laid back vibe, accented by the only local restaurant and shop out there, Millie's, which is reason enough to make Madaket your beach destination.

Best Playgrounds

Discovery Playground Nantucket.png

The Discovery Playground at Hinsdale Park

Old South Road

An amazing new STEAM-based play space opened in 2019 thanks to a collaboration between The Nantucket Land Bank and The Maria Mitchell Association. A woodland inspired theme is welcoming to both kids and adults, and it is the first fully-accessible playground on island. The equipment is creative and comprehensive, with elements designed for interactive play with both adults and children in mind.

Siasconset Playground 

4 Codfish Park Road

A great little park next to the main entrance to Siasconset beach. It’s a quick two-minute walk into Sconset, so a great place to pack a lunch and have an afternoon playing at the playground. Parking is scarce, so be sure to plan to potentially walk a couple of minutes from a spot in town. This little gem is also close to Sconset Market, Sconset Cafe, and Claudette’s.  

Where to Eat?

Family Friendly Eats

Nantucket is known for its incredible dining scene. Not only for the plethora of delicious, fresh, and local seafood but also for the variety of restaurants and different cuisines available on the island. Here are a few of our favorite spots with kid-friendly menus and environments. 


Millies Nantucket.png

326 Madaket Rd

From the shores of New England to the sun-drenched beaches of Baja California, the Millie’s menu features coastal fare and cocktails, including the island-famous Madaket Mystery. It has a great outdoor space with plenty of picnic tables, a general store, and a designated parking lot, so it is the perfect destination for a family night out. After dinner, grab ice cream cones at The Market next door and make your way to Madaket Beach for the sunset.

The Corner Table Cafe

Corner Table Cafe

22 Federal Street

Start your day at the Corner Cafe...with an excellent coffee selection, amazing menu and healthy and delicious grab and go options at the market. There is a cozy outdoor patio it's high on our list of favorite places to relax in town. They offer family meals on select days and ordering is available online. As an added bonus, it is affiliated with Nantucket Culinary if a cooking class, special dining experience or organized event appeal to you.

The Lobster Trap

23 Washington Street

This great family restaurant offers lobsters from one-to four-plus pounds, suiting all shellfish-loving family members. The Lobster Trap also offers a large outdoor seating area and a wide variety of non-seafood options on their menu, so it's great for everyone. 


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20 Straight Wharf

BBQ anyone? The Nantucket hot spot BYB is known for its amazing ribs, homemade sauces, and a wide variety of dishes. Its location on Straight Wharf makes it the perfect spot to end a day of exploring and adventuring. 

The Tavern 

4 Harbor Square

Also located on Straight Wharf, The Tavern is best known for its ‘Gazebo’ bar and delicious lobster roll. For families, it has plenty of indoor and outdoor dining space and is surrounded by lots of open space to get in some extra running around before dinner. It’s easily walkable from the ferries, town, and many of the main attractions there. 

The Sea Grille

Sea Grille Nantucket

45 Sparks Avenue

Family-owned and operated this restaurant is as embracing as it is delicious. With a comfortable, polished ambiance and a great variety of menu items for every member of your crew, The Sea Grille is a short distance from town. For this reason, it can be easy to overlook but as a local favorite, it should always be up high on your list.

The Faregrounds

27 Fairgrounds Road

For an escape from the masses, follow the locals to The Faregrounds. This laid back, year-round restaurant is home to a menu that truly has something for everyone and is one of the best places to watch a game or relax and enjoy the newly renovated outdoor patio.

The Scoop on Ice Cream

Everyone’s favorite summer treat, there’s nothing like an ice cream cone after a long day at the beach. Here are the local favorite spots for ice cream in town:

The Juice Bar

12 Broad Street

Juice Bar Ice Cream Nantucket

Sconset Market Walk-Up Window

4 Main St, Siasconset, MA 02564 (on the east end of Nantucket)

Jack and Charlie's

10 Straight Wharf

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Millie's Market

326 Madaket Road

With so many incredible spots to visit, it’s no wonder this island has become a family favorite destination for New England and beyond. If it is not yet on your bucket list, we hope it is now and expect our insider tips will help you hit the ground running when the time comes. Happy adventuring! 

What’s your version of paradise in the United States? Share your highlights on Instagram @gethappyly.

Explore more of our Dreaming of Travel series in a music lover’s paradise like Memphis, or find your happy place on Bear Lake: An Adventurer’s Oasis. If you’d prefer , Make Nature Your Focus in Harper’s Ferry, Plan Your Next Adventure in Savannah, Explore Grand Teton or Yellowstone, Dream about a Tubing Adventure in Salida, Colorado, or check out the recent blogs by Colin Boyd to further fuel your wanderlust in the Dry Tortugas or at Mojave National Preserve.

If you have a perfect getaway or a favorite landscape, please reach out to us at share@happyly.com and we will be excited to cover it! 

Thoughtfully captured by:
Ana Driggs
More posts by Ana
A place like no other, to know Nantucket is to love her.