The Essential Nantucket Bucket List
When our girls turn 10, they get a fun choice: a birthday party or special trip. So far, we’re two for two of three choosing wisely, the latter, the trip—a solo vacation with me and my mom, anywhere in the United States of their choosing. A three-generation adventure to cherish forever!
Our oldest daughter, Emmy, chose New York City two years ago. It was a dream trip, to say the least, full of Broadway, bright lights, and big-city energy. This year, our middle daughter, Hadley, picked—that’s right—Nantucket!
I know, I know. The obvious question is: How and why in the world did your 10-year-old California girl pick Nantucket, Massachusetts?
I’ll tell you exactly why! A couple years ago, I bought her a Nantucket sweatshirt. Just a simple crewneck pullover from Abercrombie Kids (a favorite!)—plain white but covered in the prettiest little coastal doodles: lighthouses, sailboats, lobsters, ocean waves. Everything postcard-worthy about picturesque Nantucket. Hadley became fixated, bubbling with questions and curiosity. I told her about the island’s world-famous charms and nautical reputation; I showed her my vast collection of Elin Hilderbrand books. We started talking about the hot spot. So when it came time to choose her big double-digits destination, her answer came swiftly: NANTUCKET!
Even sweeter, Hadley wanted to go somewhere none of us—her, me, or my mom—had ever been before, so we could experience something together for the first time. Did I mention I love this girl?
After briefly trying to steer her toward Chicago, New York (again), or something a little more kid-friendly in the traditional sense, I stopped arguing with her (after all, am I crazy?!) and decided to take this opportunity by the lobster claws. And girl, did we ever!
Is Nantucket Kid-Friendly?
Now for the second most common follow-up question: But is Nantucket kid-friendly?
I’m so happy to report that Nantucket is absolutely one of the most welcoming, family-friendly spots imaginable! Granted, Hadley is calm, chill, and a girly girl to the core—so she was perfectly content strolling the cobblestone streets, shopping, sightseeing, popping into the movie theater, meandering The Whaling Museum, and soaking in the local atmosphere without a packed agenda.
But truly I think there is something suited to most kids, especially deeper into the summer months. Gorgeous beaches, scenic bike rides, sticky-sweet ice cream cones… What more could a child (or human!) want?
If you’re considering Nantucket for any sort of momentous trip—from a girly getaway to a romantic mini-moon or multigenerational vacay—I can’t recommend it enough.
I also can’t sufficiently tout the perk of having our tried-and-true travel agent superstar, Kelly Greer with Holiday Road Adventures, take the lead on our Nantucket roadmap! Travel to ACK—especially from somewhere as far as SoCal—is not easy. Kelly was readily available not only to steer us toward the best-possible on-island experiences, but to shift flights when our first ones were cancelled due to inclement weather, make last-minute hotel and dining reservations, and overall ease our minds when natural travel kinks hit the fan.
Thank you, Kelly, for EVERYTHING—it was yet another family trip for the ages!
This three-generation vacation was, in a word, epic. Steeped in history and swimming with magic, Nantucket is more than just a pretty island—it’s a truly special place full of memory-making opportunities and unforgettable sights. It’s one of the most beautiful, distinctive places I’ve ever visited. From iconic sandwiches to harbor-front hotel dreams, here are my 20 favorite experiences from our East Coast adventure!
Foodie Favorites
1. Galley Beach: Dinner at Sunset
The Galley is an Ellen Hildebrand classic—and for good reason. Picture delectable seafood and unmatched, who’s-who people-watching as the pink-orange sun dips into the chilly horizon. Order the crabcake, ribeye, and crème brûlée, and raise a glass to unforgettable views!
2. Something Natural: Sandwiches + Cookies
Something Natural is a Nantucket institution! This picturesque shack nestled in lush greenery is the perfect lunch stop. Grab a sandwich and a giant cookie, then enjoy a picnic at the charming outdoor tables. We biked there from our hotel—pure wonder! P.S. The cookies really are as big as your hand!
3. Provisions: The Perfect Beach Picnic
Right in town and so worth the hype! My mom loved her Sicilian Tuna sandwich, Hadley enjoyed the famous Turkey Terrific, and I loved my chicken caesar salad. And, yes, we shared yet another chocolate chip cookie!
4. Pâtisserie by PPX Events: The #1 Chocolate Chip Cookie
As bonafide cookie monsters, we set out to find the BEST chocolate chip cookie in all of Nantucket. This tiny storefront took the lead by a mile, in my opinion! Above Something Natural, Provisions, Claudette’s, and more! Wow, dip into this unassuming sweet spot for the best of the best. The Sea Salt Chocolate Chip Cookie was everything and more! Behold:
5. Aunt Leah’s Fudge: YOU MUST
The ACK cookies were fab, but truly—the real showstopper was Aunt Leah’s Fudge by the pier. My friend from New York recommended it to me at the last minute and I’m SO happy he did! I’m so mad I didn’t smuggle more home!
6. The Juice Bar (Yes, the Ice Cream Place!)
This world-famous spot lives up to every bit of the hype. We lucked out with no line, but expect a wait—and know it’s worth it. The waffle cone smell alone is transportive. The flavors, oh my! We died!
7. Lemon Press: Quick, Fresh Bite
The perfect pit stop during your midday shopping spree. Superb scallop lettuce wraps, tart acai bowls, and a top-tier iced almond latte made this a favorite for all of us. Island casual with fresh, yummy flavor.
8. TOPPER’S at The Wauwinet: Birthday Dinner or Tea
A gorgeously elegant spot to celebrate anything, recommended to me by another pal and ACK pro! We were royalty for a night. While the dinner at TOPPER’S is quite formal (think long courses, cloth napkins, food as fine art), it’s a must-do, for sure! If we returned, I might opt for afternoon tea. The service and setting are d-r-e-a-m worthy!
Where We Stayed
9. The White Elephant Hotel: My Dream
Staying at The White Elephant was a dream of mine years in the making! I first heard about it from a best friend who lived in Boston during our twenties—and it exceeded all expectations. From elegant rooms to the expansive lawn, impeccable service, bike rentals, ideal location, and more, it’s well worth the splurge, I promise. Take me back!
Shops + Boutiques
10. Murray’s Toggery Shop: Nab Your Nantucket Reds!
Home of the one-and-only Nantucket Reds! Mentioned in so many books and truly a must. Murray’s is essential for your classic preppy Nantucket souvenir.
11. DAWN: My Favorite Local Boutique
My favorite boutique on the island! Chic, coastal pieces and the most inspiring story: owner Allison Deck started DAWN right after COVID with zero retail experience. Now it’s thriving, right by the ferry! Allison felt like an instant friend and so did our fashion finds.
12. Barnaby’s Toy & Art Shack: Craft Your Heart Out!
Adorable, you guys. We meandered into Barnaby’s on our last day and only wish we found it sooner! Endless art supplies, darling-and-not-junky toys, and pure joy. Hadley picked out a personalized duffel bag, and we learned about the schedule of craft classes! You must check it out if you go!
13. Cheerful Chains: Roller Rabbit, Lily Pulitzer, and Vineyard Vines
Yes, they’re chains—but these Nantucket mains feel like anything but! Each locale is chef’s kiss. At Roller Rabbit, we all got matching ACK pajamas (maybe the comfiest I’ve ever worn). Lily Pulitzer is a must-stop for a super-bright spot in your day. And Vineyard Vines—need I say more? Bright, bold, and beautiful, all three of these stores. Just walking in made us happy!
Island Adventures + Must-Sees
14. The Whaling Museum
A kid-friendly, history-packed gem. The giant sperm whale skeleton, restored candle factory, and kids’ Discovery Room were all major hits. Visit early in your trip to soak up the island’s story and get your bearings!
15. The Dreamland Theater
Perfect for a cozy, rainy evening. We saw the new live-action Lily & Stitch movie after dinner one evening and the whole experience felt like a hug. Historic, heartwarming, and beautifully restored. Complete with buttery popcorn!
16. Sconset Bluffs Walk
My top scenic stroll of the week, right out of a storybook! Even without the roses in bloom yet (they peak in June and July), it’s heaven. You’ll pass gorgeous homes—Nantucket gray dream cottages and mansions alike, all with charming name placards—and striking ocean cliff views. You’ll end at the Sankaty Lighthouse. Don’t forget to snap pics… Or to grab a cookie at Claudette’s before or afterward!
17. Harbor & Ice Cream Cruise
Yes, it’s as fun as it sounds! Frosty treats in hand, we cruised the harbor while our Nantucket by Water guide Max shared island history and hidden stories. We loved every second—and met some really sweet families also visiting ACK from around the country.
18. Cooking Class at The Corner Table
Perhaps the #1 highlight of our trip! Chef Jason of The Corner Table—“a very fine quality cafe and culinary center”—led us through homemade lobster rolls, hand-cut fries, and even made Hadley a delectable vanilla-with-sprinkles birthday cake. All Hadley’s idea, a fantasy come true!
19. Children’s Beach
We ended our trip with a beach picnic (thank you, Provisions!) on this sandy shore, fully equipped with a bathroom, playground, and glittery views of the harbor, plus the stunning homes and hotels down to Brant Point Lighthouse. 10 out of 10 for families!
For the Book Lovers
20. Mitchell’s Book Corner + Nantucket Bookworks
Saving the best (books) for last! If I did nothing else on the island, I was going to visit these bookeries! You have to pop in to both, each located on two of the cutest streets in town. Both are full of charm, coastal reads, and local titles—distinct but stunningly synergistic.
While Mitchell’s Book Corner might have a slight edge on buzzy titles and literary reads (and it’s where Elin Hilderbrand does weekly signings all summer!)—Nantucket Bookworks has a children’s section like I’ve never seen before, accessible via the most darling little arched passageway. One of the store’s many charms, this tucked-away corner offers kids’ books, Jellycats, and educational toys galore. Hadley was in total heaven! Nantucket Bookworks has more of a boutique, lifestyle feel overall than Mitchell’s—but again, I really love that two stores feel different. Don’t miss them!
Five More Things for Next Time
Even in four magical days, we couldn’t fit it all in! Here are five spots we’re saving for our next visit:
LoLa 41 – Known for their sushi, nightlife, and beats you can feel from the street, this is at the top of my list for a grown-up girls’ dinner next time!
Cisco Brewers – Food trucks, live music, and a buzzy local vibe. I lost track of the people who recommended the brewery, including Elin Hilderbrand’s blue book!
Sandbar at Jetties Beach, The Nautilus, and Pi Pizzeria – OK, three in one! All of these restaurants came highly recommended, but we (tragically) just didn’t have enough meals to fit them in!
Wicked Island Bakery – Kills me a little that we didn’t make it to this wickedly popular mid-island sweet shop! Supposedly the morning buns and handmade assortment of pastries are nothing short of sublime.
Bartlett’s Farm – As Nantucket’s oldest and largest family-owned farm, this is a longstanding local favorite for fresh provisions and seasonal produce. Farm-to-table nirvana! Can’t wait to explore it next time!
That’s all, friends! Did I miss any of your favorites? I already can’t wait to go back!
ANCHORS AWAY!
Based in Orange County, California, Stephanie Mack is a longtime writer, wife to one, and mom of three little girls. She has been blogging at MOMentary Insanity® since 2014. Her work has also been featured on Scary Mommy, Faithit, Coffee + Crumbs, and more. She holds a Master of Professional Writing degree from USC. When We Blinked is her debut novel.
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Happy Fourth of July Eve, friends!
We’re solidly into summer now—sunshine, sand, and the glorious absence of structure reigning supreme. So many things can be true of this season at once, and if I’m honest, summer knocks me off my feet every year. In great ways and hard ones! Like a toddler pummeled by a big foamy wave, I’m always both excited and overwhelmed.