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The BlueBootsGo Guide to Nantucket

If you’re either already on Nantucket or planning to go for this Columbus Day Weekend, you might be wondering what it is like and what to expect from this popular New England vacation spot. Although summer is the biggest rush with a large influx of tourists, after Labor Day, the island’s temporary residents trickle back from whence they came. One particular aspect of Nantucket, in comparison to its oceanic neighbors, Martha’s Vineyard of the cape and islands, is that it has a certain culture and vibe that I struggled to put my finger on during my first visit (yes, I’m a MA native and didn’t go till this year). While business slows down for the colder months, regulars return back to the Island for the Columbus Day weekend, and Christmas Stroll (in December) for the special events.

We arrived on Labor Day, in the start of a hurricane – Hurricane Hermine- that was at one point, headed straight for Nantucket. Imagine the irony of planning our one vacation and finding out that, whoops, Boston would be sunny and beautiful but Nantucket, 2.5 hours away, was getting a hurricane.

But, we’re a little brave and a little crazy like that, and if the plane were still running, we went through a 20 min flight in the midst of only white clouds, wondering how the pilot could see, and shook our way down to Nantucket. Upon arrival at the tiny airport, we had to brave the elements as the workers also did, pushing with all their might to get the staircase up to the plane and then having all the passengers dash unprotected through wind and rain to the terminal. As it turns out, we got one of the few flights out of Boston before the flights, too, like the all the ferries, were canceled.

I had a couple missions I wanted to accomplish that day we arrived, one being visiting my friends at wellness-minded Follain on the island. To get there, we took the Wave, a public bus that costs $1 or $2 per person per way depending on the route.  Though the bus is cheap, don’t be relieved – the island is not a cheap place to visit. Roads were blocked from earlier when they were flooded, and I was amazed to see the ocean sending water up and over into the street – the power of the weather was very apparent. But there we were, with our luggages and not waterproof gear, sloshing around, wet, and rolling our things towards Follain. They were still there – one of few businesses who hadn’t (yet) closed up shop and gone home to hunker down for the storm, or escape it before it’s imminent arrival. The warm glow was a comforting site and it was a welcome reprieve to dry off and pick up a hostess gift for our AirBnB hosts in mid-island.

Hotels were incredibly expensive in the summer, $800/night. We found an affordable deal several months ago and stayed at our first AirBnB, highly rated which is about a 40 minute walk, or 5 min walk to the bus stop and then 20 minute bus ride to the center of the one town not island, but also a short distance to Surfside beach. My plan had been to go to the beach every day this vacation – as it often is – but weather made it wet, even though the rain itself ceased the rest of the trip, and I didn’t actually have a beach day till the day we were leaving. Yes, that was disappointing for a way to start a vacation, but I was not disappointed with Nantucket and came to enjoy many of the particular local charm through adventures on a tandem bike that my husband and I took around the island. While there, we experienced what I’m calling, Nantucket air, an enduring sentiment that pervaded our stay.

Nantucket air: an atmosphere of collaboration, community, kind greetings, wet air, and a certain island je ne sais quoi melded with a casual luxury

Speaking of local charm, a brand new hotel – there are only about 13 on this 8-mile across island- opened up this week, Greydon House, and it is $299/night but with a few cool perks – a beach bag with natural sunscreen, face wipes by Ursa Major, bose speakers, and a drink cart that offers cocktails and pre-dinner drinks in your room at night. Plus, the decor looks pretty incredible – little snippets of a rich New England history that are integrated into the fabric of the buildings and communities here. Sounds good to me – I can’t wait to stay there and tell you all about it sometime. Perhaps for Christmas Stroll?

Where we Stayed

Jack – a reader and activist for conservation and reduction in food waste – and Mary Ann – an artistic francophile, were a charming pair who were decidedly young for their age and who welcomed us into the art studio portion of their home, at the head of whereowhereo road – a name which instantly transports you to a funny, whimsical place where you can’t help but wonder exactly where you could actually be. They had owned an art gallery for 30+ years with fine art, and a few incredible pieces graced the walls.

Our hosts provided us with all that we needed, and quick breakfast items, coffee and tea, recommendations, and even a flashlight for our bike since we didn’t have a bike light for getting back at night. We had a great stay in a spacious suite, and I enjoyed reading outside on a rocking chair while the cats paraded about and bees buzzed and the scent of lavender filled that wet Nantucket air, which I love.

Where we Ate


Wicked Island Bakery

If you miss the early morning rush at Handlebar Cafe, you can still get pastries from their source – but they’ll be gone by 10 am. Croissant-dough morning buns that are hefty, but chewy and and delicate in all the cinnamony-good places made it the best I’ve ever had. Maple Bacon mini donut. Peach muffin. Portuguese breakfast sandwich (a close point – even closer than Boston to Portugal, so we’re not surprised Azorean culture is present here!). Good coffee!


sandwich fixings at stop and shop – $19 for 3 days, 2 people.

The Lemon Press – juice place – smoothie, acai bowl + our sandwiches. I love the yellow stools. Best shade of yellow.

b-ACK Yard BBQ different bbq sauces from all over the country. chili+horseradish+ranch = alabama style

gold south carolina

north carolina vinegar

sweet kansas style

southwest chipotle hot sauce


summary: seafood and gourmet flavors. small seatings, need reservations (especially for Company of the Cauldron, which we weren’t able to secure a reservation after all), and intimate. Nantucket dress code – cleaned up comfortable, nothing more.





linguica (portuguese sausage) crusted cod with lobster mashed potatoes



stuffed lobster + sides = ENORMOUS



pi pizzeria

excellent ambiance, sat at the bar, delicious specials – mouthwatering risotto, cappers,  custom pie. We went and 6:30 was a good time to go – after that, even on a weeknight, it gets busy fast.

black eyed susan’s we sat at the bar, which was in and of itself like a chef’s table. bread and butter, caesar salad (a wedge of lettuce, but tasty), clam linguine, duck. They took such care arranging everything on the plate – an even span of broccoli and the duck and tendrils of greens placed with intention. Known for BYOB, you can bring your own.

shangri-la kitchen

Odd combo of foods offered – Italian food side, and Thai and Japanese, so think of it like your comfort take out food, which you can grab and go and then go watch TV at “home” 😉


The Juice Bar – mostly ice cream, contrary to the name.

Handlebar Cafe – play a game (or 3) of chess!

Where we Explored


Easy Riders in mid-island was cheaper than renting a car, and gave us a fresh-air view. You can’t take a tandem bike on the bus, however, so be prepared to bike to your limits if needed! In a colder season, I probably would recommend renting a car for a farther trek than you’re comfortable biking to, but it is a very bike friendly island. (Coming from Boston, roundabouts aren’t a huge deal, but imagine GOING THROUGH A ROUNDABOUT ON A BIKE WITH TRUCKS!!! Terrifying.)


Siasconset, or ‘Sconset and the Sankaty Head Lighthouse, in the middle of a field, by the shore which had pushed multi-million dollar homes aside, even into the last few years. wildflowers abounded, even though hydrangeas were on their last leg. Wind vanes of all kinds, and houses with funny names (sentimental to their owners, I’m sure) were ever-present and charming.

Harbor at night – we wandered there our last evening, after a particularly full dinner belly, and found a fun vibe that we would have come back to had we had

Where we Learned

Whaling Museum – some highlights – the multimedia presentation told the history of “Greenie” a young boy who left farming for the “lucrative” whaling business, as Nantucket was once the hub of whaling of the world. I cringed the whole time they described this process, but tried to step outside of the idea of it and appreciate a time in history and an economy of this island which put it on the map. The artistry of trade for the ocean soldiers,making lightship baskets (now incredibly expensive ladies’ purses, passed through generations) and these carvings on whale teeth called scrimshaws characterize a different side of the industry, where people gone at sea would tell their tales in intricate carvings. Plus, have you seen The Heart of the Sea? Moby Dick was based in part on the tales here, and the museum had on loan from the motion picture studios the costumes used in the movie.


a cool pie cutter



stargazing – milky way galaxy! Arcteus! Ursa Major! Our usual favorite planets – Mars and Saturn! The sky was painted with stars, à la Enya. Wish I could have captured this in some way to share with you.


Where we Rested

Surfside Beach

my favorite place – just add a morning bun from Wicked Island Bakery 😉




Benches by Fisherman’s Beach, nearby provide a different view. 


Where we Shopped (window-shopped…..)

more artsy, less touristy. lots of jewelry places, which would ordinarily pique my interest except I had gotten some supplies and had a few pieces of my own to make!


the skinny dip – artisan clothes

beautycounter – better-for-you


allllll over

Nantucket Looms

In the Pink


for all of you lilly pulitzer fans

Charleston Shoe Co. – machine washable wedges? I got a pair.



When it came time to bid the little art studio farewell, it was a little sad. Leaving our red chariot behind at Easy Riders, bidding adieu to the two kitties, and heading home to our urban oasis was a tad hard, but it is always good to come home.


I hope you found this guide entertaining, and as always, find my latest adventures in real time on Instagram @bluebootsgo. Thanks for coming along, and hope you enjoy Nantucket!

Until next time,



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