Nantucket Family Vacation

by Cristina | Last Updated: July 2, 2019

Nantucket is exactly what you see in the pictures. It’s quaint, idyllic, and serene.  There are flowers growing in every corner, appearing to be coordinated and hand picked to match the color of the front door.  Each home is made from the same wood which eventually grays, giving its own shape but same nautical aesthetic.  All the homes proudly display a clever name that tends to have something to do with the island or the island’s vibe. There are warm smiles, cool air, and wine flowing

Nantucket is one of those towns that you don’t find litter.  You know what I mean? It is Disney caliber landscaping and upkeep but without any of the crowds and way better weather.   The island is magical.  It’s as if you arrive, your collar suddenly pops up, you’re drinking wine all day, and saying things like “fabulous darling”.  Ok, that’s just me. Everything minus the popped collar. It just ain’t my style.

I had only heard about Martha’s Vineyard and Nantucket growing up.  I would read about it in books or a headline about the whatever celebrity was vacationing there. But I had never been.  Most Miamians don’t typically go north for the summer.  My family just always went to the Caribbean or stayed local.  When our best friends invited us to go, I didn’t see how we could pass up the opportunity.  Shout out to our best friends who are the best humans, and truly know how to vacation.

This summer, 2019, was our second experience in this magical town.  Both trips were jam packed with amazing spots for both families or just some adult time. If you are on the fence about visiting, I would definitely say bucket list worthy.  It’s a little piece of history, but perfectly mixed with modern luxury. Here are a couple of suggestions from a wine guzzling, mom of 3, and self-proclaimed foodie, and keep we did most all of this with our kids:

Galley Beach:  this beach side restaurant is one of my absolute favorite places. You can grab a drink before you dinner reservation, and watch the sunset.  If you have never seen a sun set in Nantucket, this would be the place. Of all the sunsets I have ever seen, I have never quite seen the sky look so picturesque.  Shades of pink and purple fill the sky as you finish your first cocktail, and head in for dinner after all your selfies (obviously). The food here is delicious, and changes seasonally.  They currently accept reservations 28 days in advance. Check it out HERE.    

Children’s Beach: a small sandy beach off the marina with a huge playground attached.  The best part? There is also a huge grass area with picnic tables so you can sit on the grass as you watch your kids run around and not get full of sand [unless you’re one of those parents that like to play with your kids on the playground- no judgement].  There’s a little shop where you can get snacks or you can bring your own. 

Something Natural: A little house, set on a beautiful green open space, and makes the most insane sandwiches.  Think daily fresh baked bread, freshly cut meat, and the best pasta salad- hands down. You can eat there or pick it up to go (take it to Children’s Beach for a picnic).  We have tried a few of the menu sandwiches, and the specials they have daily.  All delicious.  I also dream about their pasta salad, and may take down a container solo at least 3 times each trip.  There is space for the kids to run around, and even a beautiful trail you can take over a lilypond if you’re up to walk off all the bread.

Critter Cruise:  an hour long excursion on the Monomoy where you and the kids capture different kinds of sea creatures and fish, and learn about each before releasing it back into the harbor.  The kids absolutely loved this cruise and the staff and captain were wonderful and were so patient as they taught the kids about each animal. Check it out HERE.          

Jettie’s Beach: Jettie’s is a family favorite.  It’s a casual beach bar and grill on the beach with a mustard, aqua combination out of your Nantucket dreams.  You can have a delicious lobster roll, Bloody Mary and then just spend your afternoon laying on the sand by the water.  We have also been lucky enough to spend a sunset here with a bottle of rose and that afternoon did not suck. An absolute must.

Juice Bar: homemade waffle cones are not something I take lightly.   They have so many different flavors of ice cream, plus cookies and smoothies for those who don’t like ice cream (or have a soul).  It is worth the line that goes around the block. If anything just for the smile you get as your kid takes their first lick. 

Cisco Brewery: Beer and rose on tap, food stands, and live music what else do you need? My daughter would say a Ring Toss, and guess what?! They have one.  We have spent a couple afternoons here, and each time had to drag the kids away screaming and crying to stay.  The vibe is chill and easy.  You can grab some locally sourced seafood or some quesadillas at another stand and just take in the music.  It’s an easy uber ride away.  

The White Elephant: Another Nantucket staple.  It is set on the marina with a beautiful grass area.  In season they set out corn hole and the kids can play and walk around the greenery as you eat and obviously, DRINK.  The food here is not the best on the island, but it does have a great ambiance. There is an aggressively large white elephant here by the water, and if you don’t take a picture by it- did you even go?  

Maria Mitchell Association:  It is a small quaint aquarium, filled with the animals that you found on the Critter Cruise.  It’s just a couple of small tanks, and two rooms with some fish tanks and microscopes, but it has a great staff and the kids get a real hands on experience.  Your paid entrance also brings with it access to Nantucket’s First House Tour and the other museums in town. Across the street there is a coffee place called, The Handlebar Cafe, and it has the most delicious iced coffee and a secret garden for the kids to check out.

Bike Ride: To be clear, I did not take a bike ride.  Exercising on vacation is not a thing I have traditionally done.  However my husband and our friend went and rented bikes at, Young’s Bicycle Shop, and took a 14 mile trip down the island.  Even caught some sea turtles on one of the beaches they went to. They used a great app called The Strava App, to help guide them through.

Walk Through Town: This place is so lovely, that you could have a lovely day just by walking through all the cobble stone streets and going in and out of all the shops.  There are no big chains, just small mom and pop stores that have been there for years or newer stores with locally sourced items. My husband picked up a Nantucket Red Sweater at Murray’s.  The kids loved Nantucket Bookworks, and there is a toy store called The Toy Boat that is charming and fun for them to wander around.  Here I am pretending I like to walk around town.

Hiking: There are some great hikes (more like walks) and trails you can do.  Tupancy Links, Sanford Farms and Nantucket State Forest Hiking Trail are a few good ones to get you started. 

A Few More Restaurants:

The Nautilus: One of the most delicious meals I’ve had in a while.  You can only make a reservation for this one day of, and you do it by standing in line around 11 and hoping you get a seat.  Sounds like a huge pain in the ass, it is, but totally worth it.  The half chicken was so good one of us actually licked the sauce of the plate, and the wine list was also 100%.  This place becomes a little more of a scene with music and people crowding around the bar.  I would not suggest going with kids.

Cru: A gorgeous modern nautical restaurant theme restaurant on the marina.  The food here was out of this world, for both brunch and dinner.  It’s a little sophisticated but still kid friendly (at least for brunch).  The oysters were so fresh, and the fish and chips were stellar. For reservations click HERE

American Seasons: it’s an older more classic restaurant just outside of the main square. The menu is a little more rustic than the other restaurants we ate at, but delicious.   

Slip 14: Casual spot located off the marina.  Very kid friendly.  The clam chowder was so good, I wouldn’t share it with my husband.  Also the calamari was a sneaky delicious treat. 

Company of the Cauldron: (2021 update) Opened by Chef Joseph Kellar, and has a set menu each day.  We have just recently been to their fried chicken night and like his brother, Thomas- this does not disappoint.  I will dream of this chicken quite possibly for the rest of my life. 

Greydon House: a hotel in the middle of town that has been modernized and is absolutely beautiful.  

Windowsills and Corners:  a few of my favorite corners of Nantucket

Lodging:

Both times we visited, we stayed in the home our friends rented for the week. Information available upon request.

There were the loveliest chicest hotels that you could look into if you would prefer:

The White Elephant, The Galley, The Nantucket Hotel, Greydon House, Harborview Nantucket, The Beachside on Nantucket, The Wauwinet, Cliffside Beachclub and more.