Nantucket Guide

guide to nantucket island

The soft breeze brings in a faint smell of the ocean through my Nantucket cottage as I type these words. The sun is high and I’m fighting the urge to close my computer, hop on my bicycle, and head for the beach.

Since the first time I visited Nantucket, some 8 years ago, I’ve returned faithfully every year. And now, here I find myself stretching days out into weeks with no return flight back to LA. Nantucket for me is the epitome of quaint and a place I feel both rejuvenated and enlivened all at once.

You may be wondering why someone who grew up near Plymouth, MA never visited this perfect little island until her 20s – after she had packed up and moved to Los Angeles. You also may be surprised to learn that my parents, who grew up and lived their entire lives in Southern Mass have only visited once, and it was just recently (at my urging). You see, it’s quite simple. Nantucket feels unattainable and unrealistic. Just the ferry price alone (at close to $80 per person roundtrip) is a daunting start to a day trip. But I say this with absolute conviction: it’s worth it. Experiencing the island is worth it.


If you’re visiting ACK from out of state, I recommend flying into Nantucket airport. You will usually have a stop in Boston or NYC but it’s worth saving the headache of landing in Boston and making the long trek to Hyannis to catch the ferry. Cape traffic will break even the most seasoned LA traffic veteran. It’s brutal.

If you’re already in southern MA or Rhode Island, driving to Hyannis is the best option. The ferry is fun and easy (and the ferry bar makes an exceptional bloody mary), with multiple times offered daily. They sell out fast during the summer, so reserve ahead here. If your hotel/rental house doesn’t offer complimentary bicycles, I recommend bringing one over with you for $14. There are a few bike rental places on the island but the lines are always long and the inventory limited. Prices for rentals start at $32/day.


The rental property game in Nantucket is exceptional. You can find everything from a 10 bedroom manor to a beachfront cottage. If you choose a place far from town, I recommend renting a car or scooters on island to get around. There is a bus system as well, but I’ve never used it so can’t comment on the efficiency. Taxis and ubers are available, but very scarce. If you aren’t finding what you’re looking for on airbnb and vrbo, my friend Amber is a real estate agent with over 900 vacation rentals at her disposal. You can reach her here


Union Street Inn

There are so many adorable bed and breakfasts in town, but we had an exceptional stay at the Union Street Inn. Rooms are petite but charming and the daily breakfast was delightful. Union Street Inn offers you the perfect jumping-off point to explore all of downtown on foot.



This hotel is located on a remote corner of the island. The sprawling property touches the ocean on both sides with a spectacular secluded beach. Rooms are lovely, most with ocean views. The service is wonderful with a daily afternoon wine and cheese hour, but the dining is very limited. There is one restaurant for breakfast, lunch and dinner and no coffee shop or lobby bar. The restaurant is seriously lacking in healthy and vegan options on their limited menu as well. If you are a seasoned Nantucket-er who is looking for a respite, this is a perfect hotel for you. If, on the other hand, you are a first-timer looking to experience the dining and shopping of downtown, I would not suggest staying at the Wauwinet. Even though they offer complimentary shuttles around the island and a boat to their sister property in town (the White Elephant), it is a far drive from the main island attractions.

The White Elephant

The most infamous hotel on the island, the White Elephant will afford you an exceptional location and wonderful service – from complimentary cars to quintessential harbor views. This is the option for you if you’d most like to indulge in the amenities of a 5 star resort. Prices reflect their great reputation.


Private Yoga and Meditation Classes

well of course I was going to start with this one – that’s what I’m on the island doing! If you’d like to book me for a class at your property or on the beach, please email me at chelseagilson@gmail.com – you can find out more about my pricing and offerings here

Stroll Downtown

shoes x Carrie Forbes, Jeans x Levis

Downtown Nantucket is picturesque. Weave up and down the cobblestone streets shopping, people watching and admiring the mega-yachts and classic cars. Make sure to stop by Dawn behind the Gazebo. My friend Allison just opened it and she stocked the store with a chic selection of clothing, accessories and homeware. I might just be in there taking photos for her instagram when you pop in! (follow along at @shopatdawn)

Speaking of the Gazebo

Cocktails on the Water

Galley Beach

Gazebo makes a perfect mudslide, but I’m a big-big fan of the cult classic restaurant Cru. I’ll probably bring up their heaven-sent lobster roll 3 more times in this post, but they also have my favorite restaurant space on the island. Post up with a bottle of rosé or a spritz and drool over the multimillion dollar yachts that casually dock just a few feet from your table. The other must-visit spot for cocktails with a view is Galley Beach. I recommend going at sunset and ordering, of course, a spritz. If you can’t get a reservation (or don’t feel like emptying your bank account), next door Sandbar offers a great frozen drink selection.

Cisco Brewery

You did not go to Nantucket island if you don’t go to Cisco Brewery. This will be the first thing people bring up to you when you mention your trip. Cisco is an outdoor venue with a full creative cocktail menu, local wines and brews and tons of food-truck like small bite options. I’m a big fan of washing down a half dozen oysters with their frosé. Which is without a doubt the best frosé in the world. Cisco is located quite a ways from town. It’s accessible by bike or car.

Have a Beach Day

steps brach best beach nantucket island

The island is just an endless stretch of perfect sandy beaches. Madaket and Sconset are both good secluded spots and have food nearby to grab lunch before going down to the sand. Steps Beach is where to go for the quintessential photo opp, warm bay water and a stretch of sandbar.

Bike the Island

Biking is one of the most stress-free ways to see the island. I’ve rented from Cooks glitch-free, but there are a few rental spots available downtown. I recommend reserving a bike the day before to ensure availability.

Kayaking + Paddleboarding

I’ve rented out of Sea Nantucket Paddle Sport Rentals just a short walk or bike ride outside of town. It’s a great way to see the island from a different vantage point and you’re bound to see so many seals – the water is filled with them! Yes, that means the water is also filled with sharks.

Get an Ice Cream at Juice Bar

Just follow the smell of fresh waffle cones!


I thought you’d never ask! Nantucket’s food scene is ELEVATED. Restaurants have spared no detail in design, presentation, and meal execution – and there really is something for everyone. If you are coming to the island as a vegan or vegetarian, check out this post on all the plant-based options on island.


Cru is top 3 best restaurants for me in the world. The boogie atmosphere, the boat watching, the cocktails, the lobster roll. Oh, dear God, the lobster roll. It is beyond delicious. It’s perfect. After you indulge in all $38 of its decadence, come back and thank me. It will be the best $38 you ever spent!

Galley Beach

This is the place to be for sunset. So much so that I bet there’s not a single night all summer sans a proposal. Food and cocktails are fresh and delicious.


Great taco spot serving up delightful margaritas, guacamole and an array of tacos, salads, sandwiches and appetizers. Might I suggest the blackened fish taco plate?

Lemon Press

My fav brunch joint on the island. Aesthetically pleasing and serving up trendy lattes and healthy options.

Club Car

Pop into the cozy club car for delicious apps and drinks. During COVID, they have extended their seating to the outdoors behind the restaurant where you can sit at picnic tables under string lights. It’s very cute and the cucumber margaritas is very good.


Fun spot with some good sushi rolls and a great bibimbap. No cocktail menu.

Sushi by Yoshi

Intimate sushi spot with limited seating. Exceptional ceviche, delightful scallion pancakes, okay rolls, only serving wine and beer.

Lola 41

Technically a fusion restaurant, but I go for the sushi and the truffle fries.

The Green

Good grab and go breakfast sandwiches, smoothies and bagels.


For when you miss that specialty coffee. My favorite spot in town for a pick me up and located right next to the Green.

I’ll keep adding to this post over the summer, but for now the beach is calling my name. Wherever you are in the world, I’m hoping you find little moments of joy and peace during these uncertain times.

What to wear on the island – amazon edition

I am part of the amazon affiliate program so I make a small commission on sales made through these links. This helps me keep the blog up and running! Whether or not you make a purchase, I want to thank you for being a part of the TravelingFig family and taking this journey with me around the world. I’m so grateful for your decade of friendship – we sure have grown together!

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