Nantucket | A Family Travel Guide


I am writing to you in the crisp morning hours at Homesong Market, lavender candle lit, worn notepad nearby. We are no longer in Nantucket, but if I close my eyes and listen to the bird family that has made a cozy nest high up in the dangly antique light that hangs in the entry of my shop, I can begin to smell the salty sea, feel the breeze, and imagine sea gulls roaming the foggy sky nearby.

We went to Nantucket this summer for one month in search of adventure, connection, and home, and there we found those three, and also fell in love. Like many of you, we had been itching to travel for some time now, exploration and travel being one of our favorite and most inspiring things to do as a family, but given the current season we are in, this trip felt somehow different and more necessary. A year of being home-bound is one thing, but a year of being home-bound without a home, per se, is quite another. We had been craving home since moving last year, of feeling connected to a place, and in Nantucket, we were given that precious gift, if only for a few weeks.

The six of us are rounding the corner of what will end up being a year long restoration/renovation process of our new {old} home here in Brookside, an old neighborhood near downtown Kansas City, Missouri. And like many restoration/renovation processes taking place during a pandemic, ours has been pushed back quite a few times, making us scramble several times to find a home for our crew smack in the middle of a time when houses and rentals and various properties are not only scarce, but pricey. Back in the early springtime when we had our first setback and quickly realized we’d not be in our home this summer as planned, we figured it could be the perfect time {COVID pending} to live somewhere we’d always dreamed about. If we have to rent somewhere, why not do it somewhere incredible and beautiful and inspiring? At least for a short while. Nantucket, and Cape Cod in general, have always appealed to Andrew and I as a place we’d want to take our family one day, and given that we both gravitate towards all things historic and full of charm, this part of the country is one we’d always talked about when dreaming up our current home design. Should we go out east?

It was settled, we were going to find a way to make it work. Late one night when the kids were tucked in bed, we hopped on Airbnb, and Andrew, who is very good at and enjoys researching all the things, went down the rabbit hole of Nantucket rentals. He eventually connected with a realtor there via Airbnb who had several properties in the historic part of town, and lucky for us, they were available for the time we needed them! The catch: instead of spending one month in one home, we’d house hop around and spend one month in three. At that point in time, this wasn’t even a catch but an opportunity of getting to experience several old New England properties, a style that has heavily influenced the current design process of our new home. Move three more times, no problem. Let’ssss go!

So off to Nantucket we flew with little to no knowledge of anything but the location of our homes, which was within walking distance, we were told, to everything we’d need. Now, I am all about travel without planning and letting the rush of a new place move us like a current this way and that, but I do like to do some research, particularly around the subject of food. For this trip I did zero. Literally none. Throughout this long move I have been in survival mode running a shop + being a mom to four + healing from COVID myself, and that has left me with no time or energy to do much else. It was strangely exciting, a relief actually, to get off the plane and have no expectation as to what we’d encounter. How far was the nearest grocery store? No clue. What would we do with the kids? Hmm. Beach? And because our expectations were nonexistent, every road, every home, every hydrangea bush was met with a gasp. Was this place even real?

We quickly settled into Le Bleu house as we’d come to call it, feeling more at home than we’d felt when we lived at our last home in KC, the old Shaker colonial with the long tree swing. I cried. I didn’t even realize how much I had missed that feeling, that secure hug, of letting a space hold us as a family. What a privilege to feel home. I now understand this with more clarity, more tenderness. And while I feel I could go on and on about the feeling of home in a place, my favorite subject to ponder, I would love to share with you what we fell in love with, where we ate, played, swam, walked, biked, and lived for what I will always remember as some of the most memorable four weeks of my life. Nantucket, you are a wonder.

A few more things before I get onto the travel guide, which is probably why you are here. One, because I am not a Nantucketer or East Coast local, and because we traveled with four kids and no help or family nearby, this guide might not be the best of the best in regards to what to see and do. We very much tried our best to live in Nantucket, which for us, meant taking it very slow and steady as opposed to cramming as much in as possible. Looking back, we did a ton, but naturally, you can only do so much with small kids in tow and no car. And second, because I am not a travel writer, I am going to keep this as concise as possible, giving you most of the highlights and things we hope to do when we return. And return, we shall! It’s definitely a place that felt like home to us, and we’d love to share that experience with our extended family one day.



Nantucket | A Family Travel Guide


How to Get to Nantucket: Being from the Midwest, we could have done a cross-country road trip, but like I mentioned before, I am tired, so we opted to fly. We went through DC leaving at an outrageous time of 3 AM but, we got there around 1 PM which was really wonderful. We always try to fly as early as possible if we are traveling with the kids. We put them in their jammies and bring along their blankies to carry on and they usually, not always, but usually, snooze. I know you can take a ferry from somewhere to the Wharf, and I know that there are likely other routes, but this guide is about our experience, and we didn’t go by car.

Where to Stay: If your family is looking for a cozy New England style experience, it’s best to stay in an old home here. Homes also offer a great experience for families because they come with the things you need if living in a place, like, say, a kitchen and more room than a hotel. I suggest going on airbnb and messaging hosts {that is what Andrew did} that have places on the island. You might get lucky and get more information from a local this way. We definitely loved staying in the historic part of town with cobblestones and quaint homes because of all the charm and character. Orange Street is lovely, and anywhere off of it, grand. 

When to Book Your Stay: Right now. The further out you book a place the better deal + more flexibility you will get. 

How to Get Around: We went back and forth on this one, but because Matilda who is now one can wear a helmet and ride in a pull-behind, we decided to rent bikes for two weeks of our stay and not rent a car. And because we opted to stay in the historical downtown area, we walked the rest and Ubered or taxied a few times when needed. I love walking because you get to really take in a place with all your senses, as opposed to seeing it through glass. Everything we needed was nearby, and as long as I planned our route, we rarely required a vehicle. There are several bike rental companies on the island, and they are all very accommodating. There are bike trails everywhere, and you can in fact bike from one side of the island to the other in a fairly short amount of time. We used Cook’s Cycle Nantucket for our bike rental and had a wonderful experience.

How to Eat Like You’re Living In a Place:  It’s really important when traveling for an extended period of time to a new place to consider local markets and eating at home when able. Dining out for every meal is not only very costly, it’s not essential to experiencing all that a city has to offer. Sometimes the best meal you can have is one made with local ingredients wherever you are staying, and this is something I absolutely love to do. We have a rule when we stay somewhere for a long time: eat out no more than once per day. This excludes grabbing a coffee somewhere, but we really do our best to try and limit meals eaten out to one time a day, which means going to the grocery store or market every few days.

Because the island is fairly small, I’d get groceries whenever we were walking or biking home from the park or beach, and I kept things simple. Most days we’d either grab lunch out and have it on the go, or we’d sit down for dinner if the evening allowed. Taking four children to a restaurant is not the easiest, but food is such an integral part of travel for us, and we enjoyed those times when we did. That being said, stock up on simple meals like sandwiches, salads, egg dishes, and pastas for when you need to make a meal at home, and use as many local and seasonal ingredients as possible. I really enjoy cooking, so twice a week I’d make a special market trip to get nicer ingredients, and we used the grill and kitchen in our rental. It was perfect. 

Nantucket Markets: 

  • Nantucket Meat & Fish Market | For specialty items, excellent quality, superior picnic items.
  • Stop & Shop | For everyday groceries.
  • Bartlett’s Farm | For organic and seasonal produce.

What Toys to Bring? Because we are in the middle of a move, the kids don’t have much at home to play with anyways, so here’s what we brought + bought for them for the month to play with, aside from the beach, which is the best playground. 

  • Markers, coloring books, colored pencils, which always keep little one’s imaginations busy
  • Legos for endless building
  • Soccer ball to kick around at the park
  • Paint to paint nature like sticks and shells
  • Matchbox cars, always and forever a favorite in our home

Favorite Parks: The kids and I went to a park or beach nearly everyday as a part of our morning outings. Andrew would work from home during the first part of the day and I’d take the kids somewhere to spend a few hours outside. We would head home to do lunch and naps, and then he’d join us later, for what was likely another park or beach. Here were our favorite parks:

  • Children’s Beach | Perfect for if you want the best of both worlds, a playground and a beach. There is a little food shack right there, and it’s very close to downtown. We would always walk to this park and spend a long time there. The scenery is stunning with the sailboats bobbing in the harbor.
  • Discovery Playground at Hinsdale Park: This park is newer and better for older kids. It has a zip-line and is really large, accommodating for rascals who like to run around. It is off a bike trail and near the Meat and Fish Market, so we’d bike there from our stay on Orange Street in about fifteen minutes. Definitely the big kid’s favorite.
  • Lilipad Park: I met an Instagram friend, Kaity, at this park with her son otherwise we’d never have found it. It does not have a playground like the others, but it has a fun boardwalk in the middle of thousands of lily pads! It’s a great place to explore and bring a picnic.



Favorite Beaches: Aside from parks, we’d hit a beach nearly everyday, and made a point to try them all. Below are our favorites and what we loved most about each one.

  • Jetties Beach | Perfect for wading out in the water, little surf, fairly close to downtown. The Sandbar restaurant is nearby, and great for families. The kids had such a good time at this beach because they could walk out far on the sand and play without deep water. 
  • Madaket Beach | Perfect for scavenging for coastal sea life and scallop shells. We went here one day with the aquarium and had a great time. It’s not within walking distance from downtown, but it’s worth the bike if you can make it. This was Mister Roger’s favorite place on earth, his home “The Crooked House” was on this sandy stretch of beautiful land.
  • Children’s Beach | See Above! 
  • Surfside Beach | We ventured here on bikes on a rather windy day and were in awe of the massive waves. The kids loved it, although it was not ideal for swimming, but they played nearby the surf and it was very calming.
  • Steps Beach | A little further than Jetties, and absolutely gorgeous. It’s a hilly path that makes you feel like you are in the middle of an ocean jungle.
  • Goose Pond Walkway & Francis Beach | This was the closest beach and pond to our rentals, and we went there all the time. The kids loved the geese, and the low tide beach was lovely. Definitely a great place to explore the tide pools.  

Educational & Memorable Family Outings: Because Andrew worked during the day M-F we did most family outings on either the weekend or evenings. We definitely recommend: 

  • The Whaling Museum | For kids and adults, this museum was incredible. We learned so much about the history of Nantucket and the whaling industry that made the island what it is today.
  • Maria Mitchell Aquarium | A quaint little aquarium with a touch pool, this place was fun for the kids and they learned a lot about the local sea life on the island. We did an outing with them, and if you check out their website you can find those options. 
  • Brand Point Lighthouse | For Alfie’s birthday we rented a Jeep and ventured out to Brand Point Lighthouse over in Siasconcet, a gorgeous part of the island on the eastern side.  
  • The Oldest House & Kitchen Garden | For those who love old homes and gardens, this is a must. 

Favorite Thrift Store: If you know me, you know I can’t pass up a good thrift store.

  • Hospital Thrift | This shop is an absolute gem. I went there five times. In one month. I felt so at home there and loved all their unique treasures.
  • Bon Ton | A tiny little shack in the historic part of downtown, this thrift spot is just darling. 



Favorite Morning Eats: We didn’t eat out in the morning much, so this section is rather limited. Most mornings we usually ate Portugese bread, a local island staple you can find in every grocery store, toasted and slathered with butter and strawberry preserves. When we wanted good coffee or treats we walked to the following:

  • Handlebar Cafe | For coffee!
  • Roastd General Store | For fancy coffee!
  • Wicked Island Bakery | Get the morning muffins. They sell out fast, be prepared. 

Favorite Low-Key or  On-The-Go Eats: 

  • Provisions | Best sandwiches! They are huge and great to take for picnics. 
  • Walter’s Deli | Get the lobster roll here, it was our favorite. 
  • Sophie T’s| Awesome pizza, traditional style.
  • Pizza Gemelle | Best pizza, Neapolitan style. 
  • Sayles Seafood | Best seafood shack for fried goods and clam chowder.
  • Something Natural | Best healthy lunch. 



Favorite Sit Down Family-Friendly Eats: If Andrew and I had been in Nantucket solo this list would look much different. But we weren’t, so cheers to eating out with kids!

  • Sandbar at Jetties | Perfect if you want to eat with your toes in the sand and hit the beach before or after. A popular place for people with kids. 
  • Cisco Brewers | A great weekend spot, just remember to get there early otherwise you are looking at a line. You can count on great food and drink here.
  •  The Lobster Trap | You just gotta go here if you’re in Nantucket. It’s a rule, or something. Delicious and classic.
  • Lemon Press | Our favorite restaurant on the island! We love Persian food and this hit the spot every time. Get the nachos.
  • Millies | If you love Tex-Mex, but can get a bit pricey. It’s out at Madaket, and the experience overall is beautiful. Wonderful spot to view the sunset. 
  • Fusaro’s Homemade Italian | Just like it sounds, yummy homemade Italian, which we love. 
  • The Beet | Incredible, healthy, delicious food. We loved dinner here. 
  • Lola Burger | Great burger place!

Favorite Ice-Cream:  I don’t care what anyone says, they are both wonderful. 

  • The Juice Bar | A cult favorite, expect a line.
  • Jack and Charlies | The underdog down the street, just as good IMO. 

Favorite Small Shops: While we did not do much shopping on the island, we did enjoy these small shops while there! Do check them out. 

  • Nantucket Bookworks | I love an independent bookstore, and we went here several times to get new books on this trip. 
  • Craft | Just like the name, is full of incredible arts and craft supplies for adults and kids. Definitely go here if you need to get some creative energy out. 
  • Barnaby’s Art and Toy Shop | The best toy shop I have ever been in! Full of intentional toys and craft supplies.
  • Wheat | A lovely small boutique with something for everyone. 

Helpful hints: 

  • Make sure to look up when everything is open before you go. Some shops and restaurants have rather odd hours and we had to find this out the hard way. Don’t go by Google. Visit their online site or give them a ring just to make sure. 
  • Bikers and walkers have the right away. Use it! 
  • Most places do not have reservations open online, and it will serve you best to give them a call or walk in to dine. 
  • The island’s waste policies are very strict and it’s wonderful! Make sure you pay attention to where your rubbish is going. 
  • Walk! Bike! Get out of your Land Rovers and experience this island with all of your senses. It’s such a beautiful way to get to know a place.



There’s that! What questions do you have? Any local Nantucketers reading? Share any recommendations if you have them!



  • Lissa - What a dreamy trip! Thanks for all of the recommendations; I’m definitely adding Nantucket to my travel bucket list. 🙂ReplyCancel

    • admin - Lissa, you bet! It was such a wonderful place for us all to visit. I miss it already! xx AmandaReplyCancel

  • Shari - Thank you Amanda for this post! Sounds like a beautiful trip that served your family well. Are you able to share the specific AirBnb homes you stayed in (especially that gorgeous blue/black clad one?) Cheers!ReplyCancel

    • admin - Shari, you are most welcome! I would be more than happy to pass the relator’s information along, go ahead and send me an email and I’ll give you his correspondences.

      xx AmandaReplyCancel

  • tricia - this was so lovely to read. i’ve so missed your voice in this space, thank you for sharing.ReplyCancel

    • admin - Tricia, thank you dear one and thank you for stopping by. It feels good to be back here. Hope you have a beautiful rest of your week! xx AmandaReplyCancel

  • Larissa Audrey - Heart-warming to see you back, Amanda! You bring a special dimension to social media that’s sadly becoming rare…

    Your write-up reminds me of my 2 favourite books about Nantucket: ‘Sea Captains’ Houses and Rose-Covered Cottages’, and ‘Nantucket Cottages and Gardens: Charming Spaces on the Faraway Isle’ – dreamy reads with wonderful decor ideas. x LaraReplyCancel

    • admin - Lara, hello! Thank you for stopping by, friend. Okay, so I am almost positive that the home we stayed in has both of those books! I would wake up early and pour over them with coffee. I remember the Sea Captain’s Homes one because we were on a street with many, which naturally prompted us to try and discover what all our neighbor’s homes looked like and what their history was. What fun! I cannot wait to go back to that magical island. xx AmandaReplyCancel

  • Merrie Harrington - My family and I went to Nantucket 25 summers in a row, one Holiday Stroll, and I’ve since traveled there twice solo, to get some Steps Beach sun. Love your suggestions, because restaurants come and go, and the prices of rentals on my favorite island have pretty much prevented us from returning.

    Just one thing: it’s Brant Point Lighthouse, not Brand Point. You have instilled a wonderful sense of Looking forward to more of your newsletters.ReplyCancel

  • Paul Pavlenko - What a lovely travel guide. Thank you for the extensive info Amanda! My wife and I with our toddler Theo have been needing a vacation and this sounds wonderful!

    When’s the next rest retreat coming up? 😉

    PS- the house updates look amazing.ReplyCancel

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