A Definitive Guide to an Idyllic Week on Nantucket

July 12, 2016

Downtown Nantucket Waterfront

Nantucket I wit & whimsy

Nantucket Harbor

Nantucket, MANantucket is nothing but charm and beauty on every inch of the island. A place so relaxed you can literally walk down an Easy Street and a location where fences are covered in roses and houses in hydrangeas everywhere you look.

When determining where I wanted to spend a few days unplugging and truly relaxing (I’m not the most relaxed of travelers – ha!), Nantucket rose to the top of my list as a place I’d like to explore. My agenda was short and sweet: beach, lobster rolls, sunset cocktails, ice cream and bike rides. It was truly just what the doctor ordered.

This approachable, laid back island is the stuff East Coast dreams are made of and if you’ve never been I truly can’t recommend this idyllic spot enough. Below is everything to do, eat and drink when it comes to enjoying the best Nantucket has to offer. I can’t wait to go back soon. (And if you’re in NYC or Boston, be advised that Jetblue offers very affordable roundtrip flights through high season – be on the lookout for deals throughout the summer.)

Where to Eat & Drink:

Where to eat in Nantucket

Met on Main: One word: Biscuits. This delightful spot is open early if you want to do a delicious breakfast before you head to the beach and on weekends they even do a build your own Bloody Mary bar. (My kind of place…!)

Where to Eat in NantucketOran Mor: Recently under new ownership, Oran Mor specializes in bringing local to the menu My entire meal came off their specials menu because it all sounded too good to pass up. Strawberry gazpacho with cocoa nibs and swordfish over heirloom tomatoes. A perfectly chilled glass of Chablis topped it off and if you go I highly recommend the duck or lobster pasta which I heard other guests nearby raving about.

Where to Eat in Nantucket

Juice Bar: If you’re downtown you won’t miss this place because of the line snaking down the block. It was immediately clear people don’t come here for the juice but rather the heaping portions of creamy ice cream and freshly baked (and insanely delicious) waffle cones. I highly recommend the peanut butter chocolate chip cookie dough.

The Bean: This local coffee spot is spacious and bright and offers free wifi. They had some of the best coffee on the island I thought and an iced chai latte that may have been the best I have ever had.

Something Natural in Nantucket

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. I loved what I ordered (salami and provolone on herb bread) so much so that I went back and had it for a second day in a row. Enjoy your order outside on one of many picnic tables. (I’m actually drooling thinking of the herb bread while writing this…)

Where to Eat in NantucketCru: I liked the ambiance of this spot more than the food in all honesty (the lobster roll was overly sauced and not worth the $37 price tag in my opinion) but the terrace is beautiful for a drink.

Petticoat Row: This darling bakery offers up darling decorated lobster cookies, cupcakes and enormous muffins. I highly recommend the coffee cake muffin!

Nantucket Lobster Roll + Cisco Brew

Millie’s: I love this casual spot that is bustling with high schoolers and college students working their first jobs. I had the lobster roll and loved it.

The Tavern Gazebo: This little local hangout is just outside of The Tavern nestled right near the harbor. Sit and enjoy a cocktail before you head off to dinner.

Where to eat in Nantucket

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.

What to do:

Sunset at Galley Beach: Mackenzie tipped me off to this spot to take in the sunset and I’m so glad I did. I sipped a drink at one of the beach tables and then indulged in a crab cake while the sun slowly set from the sky into the horizon. The vibe is lively yet cozy.

What to do in NantucketRent 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) and you can leave town and head to the aforementioned Millie’s for lunch (it’ll take you 30-40 minutes.) Seriously though, how cute are the Nantucket bikes?

A Guide to Nantucket I on wit & whimsy

‘Sconset: I would have liked to spend more time here but given the distance from town I didn’t make it out past a quick visit. That being said you won’t want to miss the bluff walk between the ocean and the beautiful cliffside homes.

Nantucket Charm

Gail’s Tours: Gail is a second generation tour guide who loads up her van three times a day to provide 90 minute tours of the island. Her mother started the tours and she now carries on the tradition in a delightful manner that truly showcases how much she loves the place she calls home. I did this tour on my first morning on the island and highly recommend it as I was able to get the lay of the land and determine which spots to which I wanted to return. She also tipped me off to the $2 shuttles that run around the island which was brilliant given I didn’t rent a car.

What to do in Nantucket

Hit the Beach: Nantucket has plenty of beaches from which to choose but I spent the majority of my stay at The Jetties. It was walking distance from town (or a short bike ride), had bathrooms at a nearby restaurant and wasn’t overly crowded during the week.

Where to Stay in NantucketWhere to Stay:

The Periwinkle: If you’re looking to spend your time on the island feeling like you’re coming home every day, look no further than The Periwinkle. With an amazing location nestled in the downtown area of the island, Sarah and Gail will take excellent care of you. Sarah, the owner, has spent over 30 summers on the island and knows everyone worth knowing and the best of the best that the island has to offer. Gail, the manager will ensure you’re well situated and provide any recommendations you may need. Rooms are cozy, clean and stocked with fluffy towels and even beach bags for your trip to the beach.


You can get even more planning advice HERE.

p.s.  a New York staycation and 72 hours in Bordeaux.

(And in unrelated news Shopbop just launched a sale on sale today – an extra 25% off designer items!)

[All photography by Meghan Donovan]

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  1. I would love to visit Nantucket!

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