A Guide to NANTUCKET for the Non-Preppy


One weekend in August 2015, my friend Gracie brought me to Nantucket as her official family vacation tagalong. Nantucket is a small, comma-shaped island off the coast of Massachusetts, situated to the east of Martha’s Vineyard. This is blasphemy for any Massachusetts native to admit, but before that first trip, I had never seen Cape Cod, never mind one of the islands. I grew up with only a foggy idea of what the Cape was like. There were beaches, of course, and weathered cedar-shingled houses, and the Kennedys. In my mind, it was a foreign country inhabited by the preppiest of the preppy – a category I do not belong to.

After my second trip to Nantucket this past weekend, though, my thoughts about this weird little island have started to solidify. At first, I wasn’t sure if I liked it. It’s quiet and quaint and all those other ‘Q’ words that sound like descriptors for the setting of a Nicholas Sparks novel.  There’s charming docks and cobblestone streets and lots of men in pastel pants, a hivemind phenomenon I’m not sure I can get behind. However, despite my suspicion of too much concentrated New England charm, there are plenty of things everyone can enjoy on Nantucket, even Cape & Island newbies such as myself.

When it comes to shopping…

If you’re looking for clothes in town but are allergic to stereotypical beach vacation fashion, don’t despair. There are other options. I’m a big fan of currentVintage, whose name is a subtle but excellent pun: it’s a combination clothing and wine store. currentVintage stocks only the coolest and weirdest vintage designer fashions, along with a selection of wines and cheeses.

On the wharf and on East Street, you can find TownPool, a boutique collective that stocks all kinds of interesting artisan accessories. And if you’re looking for something heavier to stuff your suitcase with, there’s Mitchell’s Book Corner and Nantucket Bookworks. They’re both owned and operated by the same person, but Bookworks wins my heart for its non-book selection, which includes Bernie Sanders action figures, and its kids section, which can only be reached through a kid-sized doorway.

Eating and drinking…

On a small island, some institutions are inescapable, and Cisco Brewers is one of them. Every restaurant on Nantucket serves its products, so why not get them at the source? Cisco is a Frankenstein company, comprised of Cisco Brewers, Triple Eight Distillery, and Nantucket Vineyards. For a $10 cover, you can enjoy their outdoor space in which you can sample various wines, beers, and spirits, grab some snacks from the raw bar or from a trio of food trucks operated by local restaurants (Millie’s is a must), and dodge bachelorette parties.

For those who are under 21, such as myself, this is a frustrating place. Gracie and I had to stand around with black Sharpie X’s on the backs of our hands and have woefully non-alcoholic fun. Regardless, the place has a modern, fun vibe, even while sticking to the traditional Nantucket look.  (For the uninitiated, that’s gray cedar shingles and white trim, as far as the eye can see.)

Cisco Brewers - nantucket
The line to get into Cisco Brewers. Very popular!

Eating and shopping at the same time…

Bartlett’s Farm provides Nantucket residents with produce and has a Cisco-like monopoly on the local restaurants. Everything is farm-stand fresh, so come here if you ever get the chance to cook while you’re on Nantucket. If you’re not in the market for food, then check out Faherty, a tiny stall off to the side of Bartlett’s parking lot.

Faherty has an existing location in Malibu and is opening one in Newport Beach this September, so I don’t really get why they decided to put a trailer in a farm’s parking lot and call it a store. Regardless, after a two-second peek at their wares, I was in love with most of it, even if I couldn’t buy any of it on a college budget (or probably any other budget I’ll ever have).  Although Faherty is a beach brand, it avoids some of the cringier conventions of beach clothing, and kept things simple.  Their flannels felt like they could keep me warm under arctic conditions.

shopping - nantucket
Never expected to find fashion in a trailer in a parking lot.

When it comes to recovering from the first three things…

Nantucket is an island, so its border is mostly beach. And you cannot go wrong with a beach day. Everyone – from those who love salmon-colored shorts to those who condemn them – can enjoy Nantucket’s shores. Mainland Massachusetts’ ocean water is so cold that when you feel like you’ve adjusted to the temperature, your skin has just become numb. Thankfully, that’s not a problem in Nantucket, which enjoys bathwater temps in comparison. Plus, the beaches are not messing around when it comes to natural beauty. On both of our trips, Gracie and I stayed near Dionis, one of the quietest, calmest, and most beautiful beaches I have ever seen. To back that up, I have photographic evidence.

beaches in Nantucket
Sunset, sea, and grass bending under an ocean breeze.

So if you don’t like the idea of masquerading as a prep for a weekend, you don’t have to. Shop, eat, drink, and relax, and never look at a pair of salmon-colored shorts. Unless you like them. In that case, who am I to judge?  Nantucket is your turf.