20 Things You Should Know Before Moving to Nantucket, MA

Lynn Maleh

Aug 19

City Profiles

Photo by Bobak Ha’Eri, August 2004

As summer vacation winds towards its sweet, sad end, it’s not uncommon to fantasize about sticking around… forever. Approximately 10,172 people have done just that on the easy-breezy Island off the coast of Massachusetts. Every year, vacationers come and go from this quaint New England town, but a only a handful of families, fishers, and dreamers see it through the winter. If you’re thinking about making your favorite vacation spot your permanent zip code, here’s what you need to know about living in Nantucket:

1. Where “summer” is a verb. 

Photo by Le grand Cricri, July 2009

“We summer on Nantucket.” “They summered on Nantucket.” “She will summer on Nantucket this year.” On Nantucket, summer is a thing to do. Locals wait all year for the summer-ers to sail in on their ferry ships and enliven local beaches and businesses with their hard-earned tans. Summer love is not just for romance novels and common between islanders and visitors.

2. Heels aren’t recommended on the cobblestone streets. 

Photo by Bobak Ha'Eri, August 2004
Photo by Bobak Ha’Eri, August 2004

Nantucket’s adorable downtown, dotted with high-end seafood restaurants, kitschy retailers, and unique clothing shops, is known for its wide cobblestone streets. While they’re excellent in photographs, they’re a bit tougher on your tires (and feet!).

3. The houses have names. 

Photo by Martyn Smith, May 2014
Photo by Martyn Smith, May 2014

In honor of the maritime law that required every ship to have a name affixed to its stern, most homes in Nantucket are branded on hand-carved quarterboard.

4. Beaches, beaches, and more beaches. 

Photo by Henry Zbyszynski, May 2010

With 82 miles of coastline, there’s the perfect spot for every kind of beach-goer: Children’s Beach for the kids, Brant Point for watching the ships roll in, South Shore for big waves and cooler water, Nobadeer for a day party, and Cisco for surfing.

5. Watch out Crayola!

Photo by Andrew Malone, May 2007
Photo by Andrew Malone, May 2007

Nantucket has its own shade of red – officiated by The Official Preppy Handbook. It’s called Nantucket Red, and If you’re a local, you won’t be caught dead in it. If you’re a tourist, you might want to stock up at Murray’s Toggery Shop.

6. Call me Ishmael. 


While Moby Dick is set off the shores of Nantucket, author Herman Melville never actually visited the island. Between the 18th and 19th century, the whaling industry thrived in Nantucket before moving on to New Bedford. Today, you can visit Nantucket Historical Association‘s Whaling Museum to observe a restored 1847 candle factory, a gorgeous rooftop view of the Nantucket harbor, and a 46-long sperm whale skeleton. Nantucket High School goes by “The Whalers,” and the skeleton of a juvenile finback whale hangs from the ceiling of the main hall.

7. The Bread is Portuguese.

Portuguese Bread at Something Natural
Portuguese Bread at Something Natural

There’s very little information about how Portuguese bread became the go-to bread on Nantucket, but you can find it at just about every restaurant, sandwich shop, and grocery store on the island. Similar to sourdough but with a touch of sweetness, Portuguese bread makes for an unbeatable PB&J. Locals love Provision’s Turkey Terrific sandwich (think: Thanksgiving dinner between two slices of bread).

8. There’s a tiny little airport, and it was the set of Wings!

Photo by RuthAS, June 2005
Photo by RuthAS, June 2005

Yes, the planes are really that small, and there’s a good chance you’ll be the only passenger on your flight. If you love a great view, hop onboard. If you’re queasy about flying, you may want to skip. Just remember: these little cessnas are the quickest way on and off the island – a huge plus for locals.

9. The hard truths. 

Photo by Gavin, January 2014
Photo by Galvin, January 2014

Before you start packing your bags, remember there’s a reason vacation destinations draw more tourists than locals. The winters are cold, wet, and lonely, and getting off island requires a ferry or plane. While you’ll find the basics you need on island, a trip to the mall or even a fully equipped hospital means booking a ferry or plane ride. Importing requires a bit of extra effort, so essentials (like groceries) cost a premium.

10. Don’t plan to paint, renovate, or mess with history. 

Photo by William DeSousa-Mauk, April 2013
Photo by William DeSousa-Mauk, April 2013

Nantucket’s signature shingle-style architecture is protected by strict preservation codes.

11. Eat seafood. 


Eat it at Boarding House. Eat it at Straight Wharf. Eat it anywhere and everywhere. It doesn’t get better than this.

12. You don’t have to be Gatsby to dine in a Club Car

Photo by Henry Zbyszynski, May 2010

Enjoy live music at this unique train car bar!

13. Drink the local beer. 

Photo by Tim Sackton, August 2012
Photo by Tim Sackton, August 2012

Cisco Brewers’ Whales Tale Pale Ale is an institution.

14. Engage in the local culture. 


Each summer, The Cobbletone’s – a young men’s a cappella group – perform oddball, yet charming, sets in the heart of downtown.

15. Hate to break it to you Cheers, this is where everyone actually knows your name. 


With only 10,000 people calling Nantucket home, the neighbors know each other. Depending on your outlook, this can be a good or a bad thing. If you’ve got secrets to hide, move somewhere else.

16. Nantucket (formerly) Nectars 


Formerly a local business, Nantucket Nectars is no longer based on the island. It is now owned by Dr Pepper Snapple Group and bottled elsewhere. However, old timers still speak in hushed tones of those early juice blends, before the brand became famous and moved away.

17. Festive film watching. 

Nantucket Film Festival

Keep your eyes peeled in June – you’re likely to catch a few celebrities around town. Nantucket’s annual Film Festival promises a star-studded weekend full of screenings and events.

18. Where the Figawi?


What you call Memorial Day weekend, Nantucket calls Figawi. It’s the most lively weekend of the year, kicking-off long awaited summer with flocks of visitors and a 240+ regatta from Hyannis to Nantucket. So why “figawi?” As legend has it, the word was coined by drunken sailors who landed on Nantucket and slurred in their thickest New England accents: “Where the F*** awww wee?”

19. Dinner and a movie

Screen Shot 2015-08-10 at 6.14.39 PM

Date night’s solved at the Starlight Theatre and Cafe, where a dinner reservation guarantees you movie tickets. Buy your drinks at the bar and bring ’em in to the flick!

20. Ride The Wave

Photo by thisisbossi, June 2008

Not just the tidal kind! The Wave is Nantucket’s regional transit authority, and $90 gets you unlimited rides around the island all summer long.


Nantucket beckons all those who live for summer and swallows them whole. If you’re ready to try island living, check out Estately.com or the Estately App for researching available homes in the area. Download it for free today!


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Estately is a national real estate search site whose articles have been featured in the The Wall Street Journal, CNET, San Francisco Chronicle, Houston Chronicle, NBC News, Philadelphia Magazine, GeekWire, The Denver Post, and more.

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