Go there: Nantucket

As a New Englander I have loved my summer time in Nantucket.  Instagram does not lie on this one, the island is truly as beautiful as it looks through the curated lens.  The sweet cottages covered in roses, the hydrangeas that look like they can’t possibly be real and the super cute cobblestone streets all make me so happy I could squeal.. and I do! every. time.  Now look, I realize that what I am about to outline may not be groundbreaking for those familiar with the island but not everyone is familiar with this little slice of heaven, so let me break it down for those who have not yet had the pleasure.

Where to stay

Either we rent a house or stay at the White Elephant but there are many other great places as well.  I have heard good things about, The Veranda House and I stayed once at the Jared Coffin House but the room was so small I can’t really comment on much.

I have stayed in the White Elephant main house, the cottages and the village.  All are great. 

The cottages are just adjacent to the property and have a sweet little courtyard in the back.  Many different room and suite options.  I have stayed there with my mom for mother daughter trips.

White elephant main house, convenient and cozy.  Some rooms have fireplaces and balconies. Suites available

The village, perfect for families.  Some have kitchens which is great for families.  Eating some meals back at the pad is a great option since eating out can get very pricy but also not always convenient when you have little one who need to eat, like NOW.  There is also a pool on property.  You can use it if you stay in the main house but it is located at the village.

The cottage I stayed in with my mom

Lounging on the front lawn

The main hotel and the front lawn

Where to eat

Millie’s *kid friendly*, Madaket

Right next to the beach, great drinks and realllly good food. Elevated casual. Beach attire totally fine.

Greydon House, in town

Roman and Williams interiors, great food, great drinks

View of Greydon House from the street

Interiors at Greydon House in the bar area

Interiors at Greydon House in the restaurant

Cru, in town

Kind of a scene but beautiful interiors and great view.  Go for an adult night out for either dinner or drinks.

Great views at Cru

Topper’s @ Wauwinet

Get ready to spend some serious ‘do re mi’ but it is a one of a kind experience.  It is located at Wauwinet, the White Elephant sister property.  I like to go once a season.  If you are staying in or close to town you can make a reservation through the White Elephant for 5pm at the boat, you take the White Elephant boat (dock in front of the White Elephant lawn) to the restaurant and have a three course meal and then take the boat back at 8.  They serve cocktails on the boat on the way there and you can take a cocktail with you from the restaurant on the way back but after the martinis you may not need it! Great sunset and great way to take in the island.  Boat ride cocktails are free but you will feel like you deserve it once you get the bill for dinner.


Boat ride from White Elephant to Topper’s

The lawn at Wauwinet

Martini service anyone? On the lawn at Wauwinet

View from the boat as you walk to the lawn

Sunset and hydrangeas on the lawn

Met Main *kid friendly*, in town

Great hangover food. Great drinks. I like this place for brunch.  You can make your own bloody Mary’s with a mini burger as a topper. Great interior and great patio out back.

Inside at Met Main

Ventuno *kid friendly* but go early, in town

This place has the best Italian food but the back patio turns into a bit of a scene when the sun goes down.  I love sitting on the back patio for dinner and not moving as it gets crowded!

Chanticleer *kid friendly*, Sconset

This place is so charming, from the blue and white gingham table cloths to the carefully thought over garden and merry go round vintage horse this restaurant has nailed it.  The food is great.  I like a table outside on the patio.  After lunch take a walk around ‘Sconset and check out all of the cottages.

Outside patio

The Rose house in ‘Sconset

For brunch you have to go to the White Elephant Brant Point Grill.  Weekends, they have a buffet brunch that is the best.  

Galley Beach, near Jetties

Great for sunset drinks

Galley Beach

The Pearl, in town

Food is very good, Asian fusian.  Very filling!


Where to go: Beaches


This is my favorite beach. Surf is pretty tame. You can park and the beach is right there, you don’t have to hike to lay out your stuff.  The beach is also pretty wide open, you can take a nice walk and hunt for shells.  Always pop into Millie’s for lunch.  They have great Cisco cocktails and the most amazing food.  It is super close to the beach, walkable.  You can also grab picnic food at the store attached to Millie’s.  It has more elevated food choices.  You can also buy kegs here.



My issue with this beach is that it is kind of a hike from your parking spot.  Also, the food shack is the only option for food, picture hot dogs and other greasy options.  There are a couple picnic tables near the shack.  Quick and dirty but gets the job done. Beach is fine, more active surf, if that is your thing.


This beach is great. It is kid friendly and has a beach restaurant with great drinks.  The food is not high end by any means but it is fine.  There is a little shop that you can buy last minute beach things and it has a bathroom.  You walk a little bit to set up your stuff but there is a walkway that makes it a little easier.  

Children’s Beach right next to the White Elephant in town. No surf, just sand.  The only thing that weirds me out about this place is that you are in the harbor basically so there is boat oil etc.  It’s like I protect my kid all day from toxins and then throw him in a cesspool. It isn’t awful or obviously gross but it may weird you out too. There is a playground and lawn toys and a snack bar here too.  

Cisco Not for the faint of heart.  As a grown adult I am nervous standing on the sand as the waves look like they could swallow you.  On a foggy day, I find it terrifying.  If you are a surfer, this is where you want to be.  If you are looking to boogie board get ready to fight for your space brah. 


What to do for adults

Cisco Brewery *kid friendly* More than your average Beer Garden

You HAVE to go to Cisco.  This is not a suggestion.  I remember going over a decade ago when the founders were just starting out and it was a couple of guys playing bags in the back with some beers on tap.  It is now a SERIOUS operation but has still maintained a very cool laid back vibe.  They have wine, beer and amazing aptly named cocktails, The Chad anyone? Also food trucks, oysters and live music.  Kids run around and dance and it is just heaven. They also have the most delish Froze (frozen rose).  

Chicken Box, a little out of town

Ok, I am old enough to be almost everyone’s mother in here and it smells like years of spilled beer and the floor is that sticky floor that, well you get the picture but it is SO FUN! We went last year one night after Cru and the band played old school hip hop all night.  We had the time of our lives.  Go and don’t take yourself so seriously.

Cru, In town by the water

Kind of a scene but beautiful interiors and view.  Go for an adult night out either for dinner or drinks. 

Lola, in town

You need to make a reservation at exactly 4pm for a same day res to get a spot.  At 4:05 you may not get one.  They do not give preference to those who are in line vs on phone, which is annoying.  Or you need to know someone with a standing reservation.  The food is good but you really go for the scene.  Open late and very loud, you can try and pop in for a standing room only drink.


What to do for kids

Critter Cruise, from town docks

Loved this! 



Rent a bike with the trailer for them to sit in.  Great bike trails all around the island.  One of my husbands favorite things to do.  If you are staying in town, it is kind of a pain to maneuver so you may need to walk the bike a bit until you get out of the congestion.

Playground at Children’s beach

Whaling Museum, in town- interesting for adults too

Juice Bar (ice cream shop), in town- what is summer without waiting in line for ice cream while smelling the wafting smell of freshly made waffle cones?  Childhood memories made here.

A little bit out of town you can rent paddle boards, for older kids


Where to shop

Serenella (clothing)

Gypsy (clothing)

David Chase (clothing)

CJ Laing (clothing)


Milly & Grace (clothing)

Skinny Dip (clothing)

Nantucket Looms (interiors)

Bodega (interiors)