I’ve now been to Nantucket four 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.

I wrote a guide to Nantucket after five days on island in 2016 (it was the trip I took right after I left my last corporate job!) but now having returned a couple more times, I thought I’d share an updated list of some of my on-island favorites plus lots of photos! The spots included in today’s post are the ones I always look forward to going back to.

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!

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.

45 Surfside: This is a newer coffee shop that Carly and I have come 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.

Cru: 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!

Downyflake: 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!

Millie’s: This is one of my favorite dining spots on the island. Carly and I ate there twice earlier this month! The tacos, salads and lobster rolls are all so good. It’s expensive for what it is but delicious none the less.

Black-Eyed Susans: This spot had all the makings of a breakfast institution. A simple menu is offered and I highly recommend the pancakes that they freshly mix up in front of you when seated at the bar. People were waiting for a table here early on a week day so be prepared to wait any morning.

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!

Provisions: This is another stellar sandwich shop on island and right in the heart of town.

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

Renting 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).

Going for a sail: 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.

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

A favorite beach is Surfside Beach. Pristine sand, not that crowded and readily accessible bathrooms and the cutest Surf Shack serving up lunch, deliciously tart lemonade and ice cream.

Another favorite beach is Steps Beach – partly for the beach itself and partly because the homes surrounding the entrance to the beach are my favorite to view.

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

 

What I Wore:

Lilly Pulitzer Two Piece Set // Sneakers // H&M Ruffled One Piece Swimsuit (now on sale for $19! Wearing an 8) // Cuyana Navy Sweater // Denim Shorts (wearing an 8) // Everlane Collarless Navy Dress (c/o) // Espadrilles // H&M Striped Dress (wearing an 8) // J.Crew Rattan Clutch (now on sale!) // Staud Bag // Striped Shirt // Zara Woven Sandals // J.McLaughlin Cork Sandals

p.s. here is everything I packed for Nantucket this summer and wear now & wear in Fall pieces.

[Carter Fish Photography & iPhone Photos]