How To Spend A Day on Nantucket
Things to do on a Daytrip to the Grey Lady
Ah, the Grey Lady. Aptly named for thick fog that the island is shrouded in for most of the year, the gray skies dissipate with the warm weather and the dreary island comes alive for the Summer.
Nantucket is, first and foremost, a playground for the rich. Of course it hasn’t always been this way — the island got its start as a fishing/whaling outpost, allegedly dating all the way back to the mid-1600’s. It also holds the honor of being one of the settings heavily mentioned in Melville’s Moby Dick (and the islanders won’t let you forget that — seriously, every other store is covered in whale motifs (not that I’m complaining)).
Nantucket is a big island and there’s a ton to do there — it’s really hard to get a real feel for what it’s like without spending a night, but as you might imagine, Airbnb/hotel prices are astronomical in the Summer.
A caveat before we begin: I have celiac disease (the gluten free disease) and have to be very mindful and selective of restaurants. The truth is that every restaurant/food place in the town is going to be really good (it has to be when you’re completely dependent on seasonal money), so if my recommendations seem a little strange, it’s probably just because I can’t eat much at certain locations.
Anyway, here’s what I would do if I found myself planning a day trip to the Island:
In the ephemeral words of my Applied Mathematics & Process Modelling professor Dr. Smith, “start from the beginning!“ and so we shall.
For some mindset prep beforehand, my waiter at the White Elephant a couple weeks ago regarded Nantucket as the day drinking capitol of the world, and I imagine he’s not far off. Literally everything is catered towards getting (tastefully) sloshed on a beautiful island. I mean even the ferry has a full-service bar for crying out loud!
The main town isn’t huge but there isn’t really enough time in a day to leave the general vicinity. It’s definitely better to tackle the town at a leisurely pace, having a few drinks, and soaking in the views (of which there are many).
I usually take the Hy-line fast ferry that departs from Hyannis (there is another that departs from Harwich), and it always made sense to me to get breakfast in town before heading over. The Sunnyside Café is a good cheap option, and really hits that small town diner vibe. As a bonus, it’s only like a 15 minute walk to the ferry from there.
If you’d prefer to wait until you’re on island for breakfast, I’d recommend the Corner Table or Provisions Sandwiches for a quick, inexpensive bite and some coffee.
With that being said I really enjoy the ferry ride. It’s always a treat to watch Hyannis disappear behind you (lol). The salty air and ocean views are really lovely and it’s a great introduction to what is ought to be a great day.
From there it’s time to start exploring. Once off the ferry, you’re immediately greeted by great brick buildings and cobblestone streets. The town has worked really hard to preserve the architecture and environment from the 19th century, and it certainly pays off. There is a bit of a “wow“ factor, as the actual town doesn’t really track with the archetypal seaside village aesthetic. It’s almost as if a little bit of Beacon Hill was carved out and plopped 30 miles off the coast.
Main St has some really great boutiques, restaurants, and gift shops that are definitely worth checking out. Chief among them is Murray’s Toggery Shop.
If you’re unfamiliar, Murray’s is the originator of the Nantucket Red pants (still made in the USA to boot!), an idea originally taken from a popular sailcloth used in Brittany (France). The pants have since become a prep icon, with The Official Preppy Handbook proclaiming them in vogue for country club attire.
The store at large carries a great variety of brands to get you outfitted for island life. On my last trip, I picked up a Murray’s exclusive Smathers & Branson needlepoint belt depicting a whaling scene. It has quickly become one of my favorite possessions - you really can’t go wrong with whale motifs.
Of note, Murray’s was also one of the first carriers of Vineyard Vines, which got it’s start on Martha’s Vineyard, just a short boat ride away from Nantucket.
Outside of Murray’s there are also flagship stores for Ralph Lauren, Vineyard vines, and Faherty. Otherwise there are tons of boutiques that are worth poking your head into.
If you’re sick of stores, I strongly recommend checking out the whaling museum. It’s a really interesting history and is worth seeing at least once, in my opinion.
From there, head back to the big wooden gazebo right where the ferry dock is. Their frozen mudslides (alcoholic) are considered an icon of the island. If you look like you’re on the younger side they may not let you in though, as they have a history with underage tourists trying to sneak drinks.
At this point it should be around lunch time. From the gazebo, I recommend going to the White Elephant. It’s a beautiful 5-star hotel situated right on the harbor, and its restaurant comes with the option for outdoor dining with some of the best views on the island. If you’re looking to stay a night at the White Elephant, it’ll run you about ~$900 in the Summer. Good things don’t come cheap, as they say.
Right down the street from the White Elephant is Brant Point Light. Again, another icon of the island that is definitely worth checking out. Brant Point Light is the one with the giant American Flag you see on the ferry as you enter/leave the harbor.
Once you’ve gotten your fill of scenic beach views, it’s time to head back toward the town. The next stop is Cisco Brewers (another must). There’s a shuttle on Federal St. that’ll take you to their compound a little bit further inland. The last one back to town is at 7 pm though, which you really won’t want to miss.
Cisco has a fanatical cult following and is wildly popular in New England. I don’t think their beers are sold nationwide, but they were in stock at my college’s closest beer store down in Philadelphia, so they definitely have some reach. I’ve heard really great things about the Grey Lady ale, if you’re looking for a place to start.
Cisco’s spot also includes a vineyard and a distillery — they sell their own wine and spirits there as well. The vibe is nice and mellow — a great spot to kill some time while sitting back and giving your (probably sore at this point) feet some rest.
If you’re back on the mainland, you can also visit their outpost in Boston’s Seaport neighborhood — just be prepared to wait in a 2-hour line.
That brings us to our last stop: Dinner.
As I mentioned earlier, most of the restaurants in town are going to be really good. With that being said, here’s a couple of recommendations to wrap up the day:
Cru — situated at the end of the wharf, this spot has an incredible view of the harbor. With that being said, you’ll have better luck getting a table at Dorsia than you will here.
Lola 41 — “Eclectic“ Asian fusion fare. Known for its sushi and interesting drinks. Pretty high prices even for Nantucket though.
B-ACK Yard BBQ — A personal favorite. Surprisingly good barbecue right in the center of town. It doesn’t necessarily fit the vibe of a beach vacation, but it’s too good not to mention.
Wrap up dinner with a trip to the Juice Bar (another mainstay) for some ice cream. The line starts forming around noon and doesn’t really let up throughout the day. Expect to have to wait for a bit. It generally feels like the line moves pretty fast though — they seem to have a pretty efficient setup in place.
And that’s pretty much it! I really don’t think you’d want to fit much more in a single day that what’s laid out above — and if you followed this guide to letter, it may be best to take an Uber back to wherever you’re staying on the Cape lol.
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