I waited my whole life to visit Nantucket. Growing up, I watched the show Wings religiously. The quaint airport, the adorable little capes, the idea that the island is so small that every profession is filled by a single person (the mechanic, the taxi driver, the florist)… it seemed unreal to me. So last November, I finally booked us a trip to go. We were going to stay at an inn just outside the center of town, I was going to wear my most nautical clothing, we were going to rent bikes with baskets on them, go see lighthouses, sunrises and sunsets – the full Nantucket experience. We hopped a Steamship Authority ferry from Hyannis (that had all sorts of families with dogs, ftw) and off we went.
As we approached the island, I saw Brant Point Light and got ridiculously excited. Like, little kid that found out it’s going to Disney, excited.
I had all these images built up in my head of perfectly manicured lawns with white fences and Adirondack chairs positioned just so, of seemingly endless docks filled with shops and lobster traps, people riding down the streets on old bikes with little baskets on the front, of picture perfect sunsets with crashing waves, and seals who come up to say hi. Well, guess what?
THAT’S EXACTLY WHAT IT IS. It’s all that, and so many other things that I didn’t even know about.
It was the island I’d dreamed of my entire life, and when I got off the boat I broke into tears. It’s gorgeous, quaint and completely perfect. There was classical music playing faintly somewhere nearby, and the sun had started to set with the most gorgeous cotton candy colored gradient. COME ON.
Perfectly landscaped properties? Check.
Docks filled with shops? Check.
People riding down the streets on bikes? Check (although they were on the sidewalk and you’re not supposed to be – tsk tsk).
Perfect sunsets? Uh, check, check, check and check.
And those seals? They do pop up to say hey. They’ll mess with you and swim back and forth and pop up where you’re not expecting it. They’ll do flips and rolls and just generally be completely adorable.
The Club Car, where the Hackett brothers would constantly strike out and Antonio would drive everyone home at the end of the night? It’s real.
Now here’s the stuff I didn’t know about…
Like the quirky quarterboards that most houses seem to have above their front doors – Hunky Dory, Ack Two, Cobble House (because it’s in the middle of a huge cobblestone road on a hill), Ensconsed (it’s in ‘Sconset), Once Upon a Tide… so many puns.
And the traffic lights… or I guess I should say lack thereof, because there aren’t any. They only use stop signs on the island.
The way most of the businesses are intertwined with homes, and you almost can’t tell the residential from the commercial properties. It all just blends together.
I literally squealed when I saw how cute the bookstore was (spoiler alert: the inside is adorable, too).
And the coffee shop that I liked the best on the island? It has a “Bark Bar” for dogs of all heights outside, and a “Secret Garden” in the back.
You’ll never see a “For Sale” sign either. They’re not allowed. You’ll have to go see a real estate agent to find out what properties are available.
Hedges, window boxes, rose bushes and daffodils are a big deal. They have an entire weekend dedicated to Daffodils in the spring that includes a parade.
Speaking of celebrations, they line the streets with Christmas trees and have a winter Christmas Stroll in town. We’re talking Mr. and Mrs. Claus arriving in a boat and riding up the main street in a horse-drawn carriage, carolers with hot chocolate, the whole shebang. Ever seen Funny Farm where they try to trick the potential home buyers into thinking it’s the perfect New England town? It’s that – but for real.
Those salmon-colored pants are called Nantucket Reds and you find them at their original home, Murray’s Toggery Shop.
No graffiti, no billboards, no trains.
The airport uses tokens for parking. TOKENS. HOW EFFING QUAINT IS THAT.
Almost every single thing on the island is locally owned and run. There are very few exceptions, like their Stop and Shops (they have two).
So what did we do? We stayed at the most perfect, welcoming, wonderful inn.
I wore my most nautical autumn clothing, which wasn’t particularly nautical, but it felt right.
We rented bikes from Youngs Bicycle Shop and saw probably half the island that way, including a stop at Cisco Brewers/Nantucket Vineyard… because Nantucket.
Then we rented a Jeep from them to go out on the dunes of Great Point.
We saw lighthouses, sunrises and sunsets.
We bought the softest shirts ever at Annie and the Tees (and I want so many more). And I got a beautiful faux fur vest from Milly & Grace (yay for end of season discounts!)
We got cookies from Petticoat Bakery. We had a phenomenal breakfast at Island Kitchen (with freshly squeezed orange juice!). We ate mouth-watering smoked meats at B-ACK Yard BBQ. We had the best dinner of my life at Station 21… twice. Basically, we ate really, really, really delicious food.
One of the places I was dying to try, American Seasons, was closed when we were there, but it’s the top of my bucket list the next time I’m there. Just look at their front door, I mean… c’mon.
It was perfect. It’s ridiculous that this place is as perfect as it is. It doesn’t seem real. And even the people who live there acknowledge how amazing it is (and they’re all so nice), and you can tell they don’t take it for granted. We were there in the off season, which means no one was putting on a “be friendly to the tourists” front. Everyone was genuine and just plain lovely. I’ve also never related more to a sticker:
I cried when we got on the boat to leave. I was trying to come up with excuses as to why we couldn’t go home yet, I was so desperate to stay.
Confession: I love Nantucket so much that sometimes I actually want to cry because my heart hurts, knowing that the chances of me ever being able to live there are extremely slim to none. Even visiting is hard to swing, financially – at a minimum, you have to factor in the place you’re staying (which – unless you go in the deep offseason – will not be cheap), the ferry or plane ride out there and meals. When you look at the cost of actually living there? Well, for one: generally speaking, the houses start at over $1 million. Woof.
Does that stop me from occasionally pulling up the listings and flipping through photos of grey shingled cottages covered in roses, all white kitchens with weathered counter tops and farmhouse sinks, white picket fences, quirky quarterboards, and shutters with decorative lighthouse cutouts? No, of course not. Because apparently I’m a glutton for punishment.
As I sit here trying to devise a plot wherein I’m forced to visit the island for some sort of work-related, project management emergency, I’m trying to let go of the sadness I feel knowing I couldn’t be a permanent resident, and just be glad that I got to visit 🏖❤️
If you’re a Nantucket resident, I want to hear from you! How did you get there? What do you do for work? And how soon can I come stay with you (coughforevercough)? 😘