My #Preppy Summer Vacation on Nantucket

I love Nantucket.  Yeah, it’s not the most original place to go, but at least it wasn’t the Hamptons!  I visited Nantucket last year for the first time and fell hard for the cobblestone streets, the lack of major chain retailers and the laid-back nature of the island that all make it just seem perfect.  My father noted that Nantucket is the idealistic image of America in the 1950s, and he’s pretty much right.  People leave their cars and houses unlocked at all times, everyone knows everyone and there might be more American flags flying there than in DC.

Over the course of the four days I was there with the parentals, we did some retailing, a lot of eating and enjoyed some “quality family time.”

Since food’s always most important, let’s start there.

Juice Bar: The only place worth getting ice cream on the island.  You’ll almost always have to wait in a 20-minute line, even when they open at 10.  I’ll only admit to going four times, but it’s because of the Carl, a wonderful concoction of chocolate ice cream, little marshmallows and chocolate chips…in other words, someone cue Etta James’ “At Last” please!

Juice Bar

Something Natural: Yes, it’s little more than a sandwich shop, but GO! That Portuguese Bread is probably the only thing keeping me employed because I bring it back for my boss.  Also try the Matt’s Fee Tea.  I don’t know what they put in that stuff, but I could drink it forever.

Black Eyed Susan: If you want to actually eat breakfast, get there before 9 so you can be seated.  I went alone and ended up sharing a table with this super old school guy who summers on Nantucket, but lives two blocks from where I work in DC and has a brother who lives in my building in Florida.  He’s a lobbyist and since Congress is out for the month of August, he spends the whole month up on Nantucket.  I later found a note in my phone that just reads, “Find out what I need to do to become a lobbyist.”

As far as breakfast was concerned, the blueberry waffles with real maple syrup (you have to specify) and side of bacon that I ordered was like eating America with each bite!

Black Eyed Susan

Galley Beach: The food could suck (it’s actually incredible.  If you go, get the scallops) and yet people would still go because it’s right on the beach and picture perfect sunsets seem to be put on just for them each night.  The place is always packed to the gills with people and if you’re lucky enough, you’ll snag one of the lounge areas or tables on the beach itself.


Brant Point Grill: First of all, they had me at the words buffet brunch.  I love a buffet brunch because there are so many options and the only decision-making required is you deciding when your stomach can’t handle any more food!   The highlights for me were the lobster benedict, the create-your-own Bloody Mary bar (insert that emoji of the white girl raising her hand), the cranberry bread pudding, and the Juice Bar ice cream served out of an old-fashioned ice cream trolley.

White Elephant Brunch

I walked off every meal possible by retailing.

Once you get past the tacky tourist shops selling the endless supply of tee shirts and beach towels near the harbor, you arrive at the serious retail on Nantucket.  While Ralph Lauren, J. McLaughlin and yes, Vineyard Vines have all found their way onto the island in recent years, none of them can hold a stick to Murray’s Toggery Shop.

Think all Nantucket Reds are equal?  Think again.

This place actually has the trademark on the color.  They have an entire wall of their store devoted just to about every type of clothing you could imagine in Nantucket Red.  Wanna be THAT guy rocking overalls?  Murray’s has ‘em in Nantucket Red.

Note: If you don’t want the “I love swimming in my pants” look, go for their slimmer-fitting line.  These pants cost a little more, but at least they’ll look like they fit.


Closer to the boat basin is One Orange, this really cool men’s store that popped up in 2012.  Its whole focus is on things being made in America by smaller brands.  I picked up a red seersucker shirt by Jack Robie (the brand’s designer, Jon Terbell, owns One Orange).  They also had these highly amusing trucker hats, but I didn’t get one.  Trucker hats and John David don’t mix well.

There was also this great British men’s store called Henley & Sloane.  While the shirts, socks and slippers were great, what really got me was the store itself.  Old Vanity Fair sketches and sketches of Nantucket filled much of the white space while the dozens of perfectly folded shirts themselves lived in an antique shelf, each one in its own wood cubby.  When I finally buy a house of my own, I’m going to have a wall of shirts just like that.

Henley & Sloane

A friend of mine’s family has a house on Nantucket so he took me dirt-roading in a beat-up Jeep from the 80s up to Alter Rock (at 101ft, it’s the tallest point on Nantucket), sailing in the harbor (a little more wind wouldn’t have hurt.  Remembering how to sail on my part wouldn’t have hurt either) and then test-driving a Tesla S at the Westmoor Club.

While not necessarily the most ideal car for Nantucket, the purpose of the test drives was for members to get a feel for the all-electric luxury car for one of their other residences… I’m not kidding.  In all honesty, I’m not sold on the whole electric car thing.  Though I will say that the Tesla is pretty cool, it isn’t cool enough to get me to drop like 80 grand on a car that was described more like a new iPhone than a car.

Alter Rock



We rented a much newer Jeep of our own one day and drove out to Sconset for the Bluff Walk.  What’s a Bluff Walk, you ask?  Well after paying millions for, or inheriting (from Muffy, of course) a gorgeous house that has unobstructed views of the Atlantic Ocean, residents living along this three-mile or so stretch of heaven have to allow anyone who wants to just meander through their yards, tramp all over their grass and take hundreds of photos a day, even if they or their houses aren’t exactly camera ready.

The nuttiness of the concept aside, the bluff walk is amazing.  Every house looks more American than the next with the hydrangeas and the shingle houses all appearing just so.  At one point, I half expected a colonial marching band to appear around a hedge playing “Yankee Doodle Dandy.”

Bluff Walk

After dinner back in town that night, we drove to Tom Never’s Field where the site of an old bunker that Kennedy would have used if the Soviets had launched an attack while he was in Hyannis had been taken over by a carnival for the month of July.  While I skipped the rides, eating fried dough for the first time in probably a decade was worth however many years it took off my lifespan!

Before going to the airport my last day, my friend drove me out to Smith Point, an incredibly peaceful and serene part of the island that is so off the beaten path, you’re driving on roads made out of sand.

Staring out into Madaket Harbor and out onto Tuckernuck Island in the distance, I really got why people like coming to this little island.  It’s a total escape back to a simpler, less pretentious time, and four brief days, I got to escape from my world back in DC too.

Smith Point

Then I got home and locked myself out of my apartment, so clearly I didn’t stay away long enough!

-John David

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