A Whale’s Tale: 30 Days On Nantucket

We love Nantucket so much that we have a working repository of names for the home we will never buy here. (Never say never says Doug) A pipe dream of spending a month on-island, in high season no less, turned into reality when we blew fully half our annual nomad budget on a rental in Town. Between the two of us, we have visited the island over 25 times, but never for longer than a week.

Brandt Point Light from the inbound ferry

Catching sight of the Brandt Point Light from the inbound ferry never fails to send a shiver of delight down our spines. It’s like a cheerful “welcome home” for anyone smitten with Nantucket. But, Nantucket is not for everyone and that’s ok. You either get it or you don’t.

Once we stood in line for the last ferry of the day behind a day-tripping family who couldn’t wait to leave. Their kid summed it up: “Yeah, there’s, like, nothing to do.” Wow. Harsh. Maybe Nantucket isn’t a great day-trip spot, but we’re gonna say that’s on the trip planner. But hey, to each their own, and shoutout to that family for getting off-island and making the Juice Bar line just a little bit shorter.

Our Nantucket

Nantucket is Full of Surprises.

Yes, it is the playground of the rich and famous – yachts, galas, and mansions we glimpse from behind perfectly groomed privets and accessible only in a perfectly restored, baby blue ‘75 Ford Bronco with the top off.

But that’s not our Nantucket.

Our Nantucket is casual, chill, beachy, and blissfully indifferent to social status or political connections. It is a visual jewel no design enthusiast can resist, every home worthy of its own Insta, with paint so perfect, hydrangea abloom, seashell driveway, and flower box joyfully overflowing. It’s a beautifully polished antique, still rooted in its whaling past

But yeah, it’s pricey as Hell. Privilege is part of the package even if you’re not dining at Cru every night.

Jeep in action

A Tiny Island, Big Logistics

Nantucket spans just 14 x 3.5 miles. You could walk the length of it in 5 hours, and the width in one. You do not need a car. And while we absolutely hate people who drive on Nantucket in season, we also are those people. When you have surfers in the family, driving can be a necessary evil, and it sure does make the all-important grocery stock-up at mid-Island Stop and Shop a lot easier.

The cost to rent a 4×4 on-island is $2500/week, or $10,000 for the month. We opted to ship our Jeep across the country for a fraction of that cost. Watching the AirTag move from state to state was surprisingly satisfying, but also a bit annoying because the car emoji faced in the wrong direction.

On-Island Arrival

We received our Jeep from Sherpa Auto Transport and hustled to the sloooooow ferry to Nantucket, a high-stakes and stressful reservation that needs to be made in January, or good luck getting a car there at all. There are many more options for a fast foot ferry, taking an hour or so depending on your point of departure.

The 2.5-hour slow ferry is a throwback to a less hurried era—a fitting mode of travel for our unhurried stay. The bare-bones, retro travel vibes were strong, with nothing but a handful of hard benches to sit on, one of which we threw elbows to secure, and a broken vending machine where the fast ferry’s clam chowder-serving cafe would have been.

Many would concede defeat, giving up on the idea of a civilized journey. Who really finds it necessary to have a charcuterie board and a cold beer on a ferry? That would be us. We do. Thank goodness we did a big grocery shop on the Cape and had the necessary provisions in the car.

Transit Nantucket style

Biking: The Real Way to Get Around

Given that the car is only for necessities and that we, very recently, were Dutch, it should come as no surprise that our preferred mode of transit as Nantucketers is biking. We purchased used bikes from Young’s Bike Shop and donated them at the end of our stay, a considerable savings vs renting, but at $300, still far more expensive than our €29 SwapFiets from Amsterdam.

Nantucket has an excellent system of bike paths, thanks to the Land Trust, that keep you safe and blissfully away from traffic. But first, you have to survive getting out of town.

Will your downfall be your front tire wedging perfectly between two cobblestones, launching you over the handlebars? Or maybe you’ll get clipped by that perfectly restored, baby blue ‘75 Ford Bronco that’s a little too optimistic about Nantucket street widths. And let’s not forget the head-on collision potential when you choose the wrong-way street, because it doesn’t have cobblestones and that seems safer.

Having Escaped Town

Should you escape town with your bike and dignity intact, you will find that the rest of the island is paved and gloriously flat. Just watch out for that headwind. It’s always coming from the direction you’re headed, no matter which way you are going.

One kid put it best, shrieking, “I HATE THE WIND!!!!” as he pedaled furiously yet gained zero momentum. Cue Doug, deadpanning, “Look at me! They gave me the backwards bike!” as he dramatically reversed his pedaling, distracting with humor. Thus, the not-very-funny-but-endlessly-reused backwards bike/boat/car joke was born.

Back in the day, Centre Street rental +

Staying in Town for One Month

We stay in, or close to, Town, except for the time Kate and Charlotte stayed at Hummock Pond with the family they were babysitting (they were tweens) and the time we stayed with Kate and Sloan in Madaket (we were poor). Town is not for everyone, but we love it. We’d rather ride to the beach and walk to the bar (we make an exception for Cisco Brewery). The antique homes are in town, and we are here for the antiques.

Entering an original Nantucket home is like stepping into a living piece of history that’s been lovingly weathered by salt air and sea breezes. Think low, beamed ceilings that make anyone over six feet tall immediately duck, secret Amsterdam-narrow back staircases, wide pine floors with just the right amount of creak, and windows perfectly imperfect. Our favorite hug from the past, just so long as the kitchen and baths have been updated.

The house we rented was on Centre Street. No, that is NOT a typo, and was built in 1850, with 3 bedrooms in the main house and 2 in a backyard cottage, perfect for the visitors we hoped to host, should the island allow it.

Just Try to Get Here, I Dare You

Nantucket is like that mysterious friend who lives off the grid: it doesn’t want to be found, throws a tantrum of fog, wind, and canceled flights to keep you away, and when you finally do make it there, it clings to you like blubber to a whale making sure your escape is even more complicated than your arrival.

Like when Jackson came for a quick trip before his very first day of work at his very first job. His flight was delayed, delayed, delayed -canceled. We got him on the last ferry out, by the skin of our teeth, and put him in a car service, which rolled into Manhattan at 4 am just in time to go straight to work. Meanwhile, the rest of us had developed hives and were questioning our life choices. Thanks for that, Nantucket.

The Routine

Lucky for us, many intrepid visitors did make it and settled with us into our routine. Every day (for whoever is not sitting around the dining table on Zoom calls) starts the same way with a 3-mile walk, a loop first envisioned by Jill and now embraced by all.

Some people try to stroll on this walk, but this isn’t a casual thing—this is for exercise. Charlotte is always hoping Doug will switch out of his laid-back island pace and into his “airport mode,” a race-worthy tempo that only seems to activate in airports, and suggests we are very, very, very late, though we usually are not.

Steps to Steps Beach, Brandt Point, The Dinghy

The Route

The walk starts at any point in town, then heads past the Cliff mansions with their pristine paint, ridiculously prolific hydrangea, and roof walks, down the many steep steps to peaceful Steps Beach, along the sand past the Cliffside Beach Club, where kids can swim, but only from 10-12:30, (currently up for sale if anyone is interested) and Galley Restaurant, where you can dine with your toes in the sand, on a delicious, but overpriced meal and plenty of stale bread.

Continuing past the sweetest little home we’ve ever seen, with its private stretch of sand, and the site of The Dinghy, our favorite ACK rental, a one-room shack, tucked behind a dune, that we rented several times when the kiddos were babes and is long gone.

Past Jetties Beach and the infamous Sandbar, where you can drink with your toes in the sand, but only if the bartender sees fit to take your order and only if he can hear your order over the EDM playing at Manhattan-club volume.

“Sunken Ship”

On towards the picture-perfect Brandt Point Light, passing the Brandt Point homes with their classic charm, perfect gardens, and harbor views. Scooting through the White Elephant and along the wharf past Children’s Beach, Jerry Stiller’s (RIP) home, and the little red rowboat named “Sunken Ship” floating in the town harbor.

And, Coffee

Always, always ending at Handlebar Cafe for cappuccinos – oat, extra hot, served by polite and hard-working local kids.

Sufficiently fueled, it’s time to tackle life’s big decisions—like which sun-drenched beach is calling our name, what sandwich is about to change our lives, and where we should toast the sunset with a cocktail in hand. Click here for all our top picks!

Having the privilege to spend a month on Nantucket exceeded our expectations. So many things made it great, but these top the list:

ACK 🐳🐳🐳🐳🐳 What Makes it Great

Dreamy hydrangeas, grey-weathered shingles, window boxes and sea-shell driveways
Not needing a car (even though we did have a car)
Stopping at Cisco for a brew and some great live music, then later belting out songs at the Club Car
The crab fried rice at The Nautilus and the epically fresh seafood at Raw 167
Living in a dreamy antique but with a modern kitchen because who says you can’t have both
The stupid cuteness of ‘Sconset
Our 3-mile walking loop, ending at Handlebar with oat cappuccinos, extra hot. Obviously.
The treasure trove of shops in Town
It knows how to throw a party – July 4th, Stroll, Daffy, but also might throw a storm and not let you in.
The line at the Juice Bar that makes you feel lucky to be there, not annoyed.

Next stop, New York City!