An Off-Season Visit to the Island
For someone who's called Boston home on and off for the past decade, it's cringingly embarrassing to admit that until a couple weeks ago, I'd never set foot on Nantucket—just 30 miles off the Cape towns in Massachusetts.
What I didn't realize as a first timer was everything from shops, and accommodation to restaurants and beaches are within walking distance of the historic downtown area clustered around the port and bordered by national conservation lands. Though there are a handful of beaches across the island that may require a car to reach, for the most part, the island is incredibly walkable (or for the pedal-enthusiasts, bike-able), which helps to build up an appetite... trust me you'll need it for all the fresh, local seafood and #goodeats islandwide.
As with many of my trips, I felt like I spent the majority of my 48 hours on the island restaurant hopping. That's because you really can't go wrong with eateries on Nantucket—from New England favorites of fresh oysters and lobster rolls to treats like whole fish and lobster tacos, I certainly couldn't experience *every* restaurant over two days, but I sure tried.
Since I visited on the cusp of fall (mid-September), I knew the weather may be iffy, indeed, at peak sunshine, a t-shirt and jeans barely sufficed, and come nightfall, a sweater was a necessity. While I pretended it was still summer when I packed my weekend bag, I'd suggest paying a little more attention to the weather, and certainly packing a pair of pants and warm sweater no matter the time of year you visit as locals warned that the beachside chill can creep in past sunset even during the summer.
In addition to eating (and drinking!) there was a whole lot of gallery viewing and shopping. Quite literally everything in the historic center is worth popping into, even the General Store! After the first afternoon, I quickly decided 48 hours wouldn't be nearly enough time to conquer it all, but I made the most of it, narrowing down my favorites in the categories that follow, to ensure I don't overwhelm you, as I overwhelmed myself with my eager to-do list.
And, might I just add, though the chill was unignorable, visiting at the start of off-season has perks, as with any destination. There was more availability for reservations, less crowds, and a local's only kind of atmosphere that drew me in.
ACCOMMODATION
Life House, Nantucket for a home-away-from-home feel and an eclectic introduction to the island by way of the island's newest boutique, yet oldest inn on the island. Don't miss out on their nightly happy hour around the fire-pit where being shy isn't an option; have a drink or two, or three and be sure to strike up conversation with your fellow guests. You never know who you might meet or what recommendations they may inspire.
RESTAURANTS
Cru for dockside oysters at lunch.
or, The Whale for the most ridiculously tender grilled octopus skewers (seriously so mouthwatering we almost orderd a second after splitting the first!)
The Proprietors Bar for a sharing-style dinner with your bestie.
167 Raw for a casual, afternoon snack (looking at you, lobster rolls!) or picnic haul (think: shrimp and crab meat).
Lemon Press for a brunch/lunch with your classic options from eggs and wafflies to acai bowls and kimchi rice bowls (plus smoothies and juices galore!)
Galley Beach for a toes-in-the-sand, beachfront happy hour.
Cisco Brewers for an afternoon of food trucks serving up everything from fresh oysters and fish tacos to lobster spring rolls with a side of beer.
SHOPS
D Dream, Shari's Place, Salt for women's fashion and jewelry.
Current Vintage, Sapphire Sea Vintage for a variety of antiques and consignment.
Bodega for dreamy home decor.
Plus, don't miss the variety of jetty shops offering souvenirs to intimate clothing and accessory outlets.
GALLERIES
Samuel Owen Gallery for contemporary art.
Quidley and Company for fine art.
The Gallery at Four India Street for a range of fine art, sculptures and glassware.
DO
If you aren't as interested in eating and shopping—or simply need a break—hit the beaches, Madaket Beach, Steps Beach, Surfside Beach, or check out:
The Whaling Museum
Brant Point Lighthouse or Great Point Light
Rent a bike and explore the island while enjoying the fresh air and stopping at various food trucks on the way.
Take in the views on the 'Sconset Bluff Walk or on any of the island's designated trails.
Go fishing.
Rent a boat or book a boat excursion.
Xo,
J