Updated July 21, 2020.

It’s Travel Tip Tuesday, and this week I’m letting you in on the things you need to know before your first trip to lovely Nantucket! Here are a few of the essentials to help you be as prepared as possible.

Some Terminology

• Summer: This is a verb in Nantucket. People come for the beautiful summers, so they “summer” here. “We summer on Nantucket every year.”
• On-island: The reference made for people, things, or events on Nantucket. “You’ll get the best ice cream on-island.”
• Off-island: What it’s called when you leave the island. “She went off-island.”
• Roofwalk: Elsewhere known as a “widow’s walk.” Whalers could be out at sea for 3-5 years. Women did not go out on the roof every night to watch for their husbands, fathers, sons, and brothers for that long–they had a town to run! A guide with the Nantucket Historical Association told me the roof walks started as a safe way to get on the roof and douse a fire in the chimney, and they got more refined from there!
• Shakes: The cedar siding on all the houses are called “shakes.” Only a few homes are allowed to have regular wood siding or bricks. Everyone else is required to use the cedar shakes so the island has that uniform, historic look. They go on yellow, but in about six months they turn that iconic bluish-grey color!

Coming In

The Best Time to Go

According to Captain Jim of the sailing ship Endeavor, the best time to come to Nantucket with the fewest people but the most sites, shops, and restaurants open is the week after July 4 or the time between Labor Day and mid-September. The waters are finally warm enough by July 4, but it’s one of their busiest weeks because of the holiday; the week after is just as nice and warm, but people have just come for the week and they’re back at work.

Labor Day weekend is also very busy, but the summer season is coming to an end, and people have to go back to work. The weather starts to get nippy, and shops and sites start to close around September 15. I don’t know about September, but I do know that the week after July 4 greeted me with the most beautiful hydrangeas!

Compare Taxi vs. Uber

When I went to Nantucket on a Monday and came back on a Wednesday, the price for a taxi between the airport and downtown Nantucket was a $16 flat fee (plus tip). I compared that with Uber, and the same ride was more than twice that amount! Uber was surging, but I’m not sure why, and neither were the cab drivers! Check Uber while you’re there, but I advise a taxi if the charge will be more than $20!

Etiquette and Attire

Nantucketers are Very Welcoming

I was pleasantly surprised at how friendly the people of Nantucket were. A sweet man at the Shipwreck and Lifesaving Museum told me it’s due to the many shipwrecks on the shoals around Nantucket. Everyone had family or friends out whaling for years at a time, and they knew how devastating it was to lose a ship and perhaps your shipmates.

The people of Nantucket would welcome people to their island and into their homes. People actually stop for you in the crosswalks, wave when you walk by, smile and say “good morning,” and they even sit and chat with you over breakfast! I felt like I was back in the South.

Wave a “Thanks” When Someone Lets You Cross

That said, it’s common courtesy on-island to wave and say thank you to the drivers who let you cross in front of them. They might be friendly and all, but they get annoyed just like a regular person would when they don’t get a little wave of thanks!

You Might Run into a Celebrity

It’s true! Nantucket is the summer playground of the rich and famous. Please don’t try to strike up a conversation or ask for a selfie. This is their vacation, after all. Just stand behind a bush and snap a picture without them knowing like a regular person! Celebrity trainer Kira Stokes and her husband were there the same time I was, and she even posted pictures from a hotel on the same block as me! But I didn’t see her while I was there. Maybe you’ll be luckier!

Ladies, High Heels are Out

Those cobblestone streets are no joke! I know you want to look your best on the classy, high society island of Nantucket, but tasteful flats can get the job done.

Background Information

It Gained World-wide Notoriety as a Whaling Port

You’ll find remnants of the whaling industry everywhere. Be sure to check out the whaling museum while you’re in town! Your admission ticket is good for the Whaling Museum and the Nantucket Historical Association historic sites (the Oldest House, Fire Hose Cart Museum, Greater Light House, the Old Mill, and the Quaker Meeting House).

Keep reading: 10 Reasons to Visit Nantucket

The Women Ran the Show

Many Nantucketers adopted Quakerism as their religion. Quakers believe that men and women are equals–quite a revolutionary idea in the 17th, 18th, and 19th centuries! They took on the jobs men would traditionally do while their husbands, sons, and brothers were off whaling for years at a time!

There was a devastating fire in 1846

While the historic buildings are indeed historic in their own right, very few of the original buildings prior to 1846 survive. The fire started in a hat store on Main Street and spread through town and down to the docks, where barrels of whale oil were stored. You can imagine the devastation when the fire reached the barrels of very flammable oil. By the end, over 250 buildings had been destroyed. This event also contributed to the Nantucket whaling industry’s downfall.

The Lay of the Land

Great Point Light House is a Trek

I didn’t make it out to the Great Point Light, but if you want to, you’ll need to rent a 4-wheel drive vehicle and lower your tire pressure to 15 psi (pounds per square inch) for the 7 mile beach drive to the light. Be careful out there!

Nantucket has a Land Bank

When someone purchases land on Nantucket, a certain amount of land goes into the Nantucket Land Bank to be used as public property. That makes so much of the island accessible and enjoyable! On my bike tour, we used the public land to visit some of the sites, including the Lily Pond!

You can get a free bus pass to the Shipwreck and Lifesaving Museum

Yep! The museum is far enough outside of town that it’s not within reasonable walking distance. You can ride a bike there easily, or take a rental car, but you can get a free pass for the bus to Sconset via Polpis at the Visitor Center at 25 Federal Street. The Wave bus picks you up on Washington Street between Salem Street and Coffin Street, and the bus starts at 10:00am and runs every hour and 20 minutes until 4:20pm. You will also receive a free bus pass at the Shipwreck and Lifesaving Museum for your return trip!

More here: How to Spend 48 Hours in Nantucket

On the Way Out

Airport Passenger Screening Opens Around 9:45am

There were some earlier flights on Cape Air and possibly one other airline, but the next flight out is the 10:35am United flight to EWR (Newark, NJ). They made an announcement around 9:45am that the security line was open, and those of us on that flight filed in, went through security (including the body scanner as opposed to the walk-though metal detector), and walked over to the gate to wait for our flight to board. It’s a cute airport!

There is No TSA Pre-check—Sort Of

There is no separate TSA Pre-check line or special screening. You’ll be given a yellow card that indicates you are a pre-check passenger, and you can keep your shoes on. But sorry! Your laptop, liquids, belt, loose change, etc. will have to go through just like everyone else.

Wings Was Set Here, but Not Filmed Here

If you’re a fan of the 90’s TV show wings, Nantucket may already be on your radar as a “place to visit!” It was definitely set here, and the opening scenes in the early seasons were filmed here, but they did not film the show here week-to-week. The airport you see is their old airport; since the filming of the show, they built a new one, which is the one you’ll be flying into. But Tom Nevers Field was never an airport. It’s a park on the south side of the island! I did, however, find some of the characters at the restaurant in the airport:

I caught up on Wings on Hulu before I visited, and I recognized a lot of the street names and, of course, The Club Car. It was a bit over my price range, but I had to get a shot out front!

So are you ready for your trip to Nantucket? Get all the information you need and more on my United States Page!

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