Nantucket Guide

July 13, 2023

Nantucket Guide I wit & whimsy

I’ve now been to Nantucket five times and every time I leave I truly cannot wait to go back. I feel similarly about Nantucket to Paris…it has a little magic that charms you every time; leaving you wanting more. This island off the coast of Massachusetts isn’t accessible by car so you’ll need to fly onto it or ferry onto it.

Nantucket Guide

The spots included in today’s post are the ones I always look forward to going back to.

Nantucket Summer Outfit White Dress

Nantucket Guide I wit & whimsy

Nantucket Summer Outfit on the beach

Nantucket Guide I wit & whimsy

Where to Eat on Nantucket

Juice Bar

My #1 destination always and forever. If you’re downtown you won’t miss this place because of the line snaking down the block. Their creamy ice cream and freshly baked (and insanely delicious) waffle cones are addictive. I highly recommend the cookies & cream, chocolate chip cookie dough or peanut butter chocolate chip cookie dough. And the best rainbow sprinkles ever!

Meghan Donovan I wit & whimsy on Nantucket

Lemon Press

This is a newer spot on the island right on the main street and it offers up lots of healthier fare like avocado toast and smoothie bowls. They also have a great takeaway for coffee and juices.

The Proprietors Bar & Table

I absolutely wouldn’t recommend this place for a party of more than two unless you’d like to go into a small debt because the prices are so high and the portions are so small. That being said, for a party of two – the dishes are perfect for sharing and everything is delicious. Don’t miss the half chicken.

Nantucket Guide I wit & whimsy

45 Surfside

This is a coffee shop that Carly and I came to love as it is a short drive from the house she rents and they have great, great coffee and a beautiful, airy space with an outdoor patio spot, too.

Something Natural

There’s nothing special about this casual joint when it comes to the bones of the place but man, are their sandwiches delicious. Don’t miss the Portuguese bread. The herbed bread is a close second runner up for me. Enjoy your order outside on one of many picnic tables or take it to go and eat it on the beach.

Bar Yoshi

Everything I ate at Bar Yoshi was delicious. They serve Japanese-Asian inspired seafood including ceviche and sushi but don’t miss out on their dumplings and even the sweet potato fries, too.

Nantucket Guide I wit & whimsy


This place has grown on me since I first went in 2016. I love the waterfront setting and their lobster roll is so good. Bonus? The fries are delicious!


This diner is famous for their doughnuts and for good reason. So inexpensive, so fresh and so delicious. The chocolate is my favorite but the coconut is a close second!

Nantucket Guide I wit & whimsy


This is one of my favorite dining spots on the island. The tacos, salads and lobster rolls are all so good. It’s expensive for what it is but delicious none the less. They also have a small outpost at Cisco Brewers.

Born & Bread

Divine breakfast pastries and breakfast sandwiches have a line out the door at this spot but fear not – it is worth the wait! I highly recommend their Cruffins in a variety of flavors and the sausage, egg and cheese sandwich on fresh sourdough bread.

Nantucket Guide I wit & whimsy

Nantucket Guide I wit & whimsy

Galley Beach

This upscale place is right on the beach and boasts beautiful views of the sunset. A more upscale menu but the views make it worthwhile.

Club Car

This Nantucket institution is great for a drink and my next time to Nantucket I want to check out their food, too!


If you want to listen to some live music and do some dancing at a divey spot – this is a great option right in town. And for more of a scene – take a quick cab over to The Chicken Box – an island destination for dancing and late night antics.

Nantucket Where to Eat Guide


This is another stellar sandwich shop on island and right in the heart of town. The breads here are amazing and I highly recommend the Sicilian Tuna and the Italian sandwiches at this delightful spot.

Be sure to wander the town and explore all of its nooks and crannies and the waterfront areas. There’s so much to see.

Nantucket Guide I wit & whimsy

Nantucket Travel Guide

What To Do on Nantucket

Rent a bike

Biking almost seems like the main mode of transportation on Nantucket and I can understand why. It’s a beautiful way to see the island and there are plenty of spots to rent from in town. I recommend Cooks Cycles (the day’s rental will set you back $29).

Nantucket Guide I wit & whimsy

House Hunt

If you’re in the market – good for you! But if you’re like me, you’re just dreaming. But it sure is fun to wander the various neighborhoods and see people’s front yards and beautiful landscaping and driveways!

Nantucket Guide I wit & whimsy

Go Sailing

There’s loads of boat companies that offer a variety of sailing options to get you out on the water and get the ocean breeze in your hair.

What to do on nantucket

Spend the afternoon at Cisco

This brewery serving up cocktails and locally made beers offers has a variety of food trucks for you to feast at. It is such a fun and happening scene and perfect for all ages to enjoy.

Explore ‘Sconset at Golden Hour

I wrote more about this neighborhood here and definitely think it is a must-see.

Nantucket Guide I wit & whimsy

Hit the Beach

My favorite beaches include Surfside: Pristine sand, not that crowded and readily accessible bathrooms and the cutest Surf Shack serving up lunch, deliciously tart lemonade and ice cream and Steps Beach. Descend from a hilltop down the steps onto a beautiful and lively beach. The homes surrounding this beach are some of my favorite to wander by and dream about. 

Nantucket Guide I wit & whimsy

Where to Shop on Nantucket

Where to Shop on Nantucket

A few favorite stores in town? Milly & Grace, Erica Wilson, Nomad, Hill House, Nantucket Looms, SkinnyDip, J.McLaughlin, Beautycounter, Parchment, Peter Beaton and Mitchell’s Book Corner are all worth wandering into.

Two Piece Eyelet Set on Nantucket I wit & whimsy

Nantucket Summer Outfit

What to Wear on Nantucket

Getting ready to pack up for a trip to Nantucket? If going in peak season (aka: summer) you’ll want necessities like a sun hat and SPF but you’ll also want breezy linen dresses, evening attire for dining out, swimsuits and plenty of good button downs and shirts and knit tanks.

Shop My Nantucket Wardrobe



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[Carter Fish Photography, Allie Provost Photography & iPhone Photos by Meghan Donovan]

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comments +

  1. Libby says:

    The light on that island is unreal! I get why people say it is magical!! This guide looks perfect! Nantucket is at the top of my list, and I am still hoping to maybe squeeze in a weekend before the end of summer! Thanks so much for this, Meghan!

    xx Libby

  2. Julissa Garces says:

    Thanks for sharing! This is a great guide for someone who is planning to go visit. Looking forward to a visit 🙂

  3. Cynthia says:

    Nothing better than hydrangeas! They just scream summer to me and remind me of my parents house.

    Love the proportions of the denim cut offs and shoulder pad blouse. You look great.

  4. Kate Scott says:

    Love love that Everlane shirt dress!

  5. Pam says:

    You really hit the nail on the head! I love Paris and Nantucket and there are so many reasons; the light is definitely one. We have been spending July on the island for about five years. We just left and I can’t wait to go back; we love to go in the off season-fall and we went to the Daffodil Festival this year. A big plus for going off season is not as crowded; a big minus is the Juice Bar may not be open.

    • Meghan says:

      How amazing to spend a whole month there! I would love to go in the Fall sometime too – had no idea they did a daffodil festival – how fun! So glad you liked my guide, Pam 🙂

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