It’s not the Nobadeer Nightmare of Fourth of July debauchery, nor the native land for every New England Chad. Find Nantucket past Labor Day and she’ll be ripe as a Massachusetts peach.
Cobbled streets cleared and beaches still warm with lingering summer sun, the perfect time to be on Nantucket arrives with fall. This Indian summer sweet spot misses the crowds, but catches all the best restaurants and stores of summer (think raw bar at Cru and sales at Skinny Dip) before they shutter for the winter on Columbus Day weekend. So if you’re feeling a long weekend coming on after a few interminable post-summer workdays in the trenches, touching down on Nantucket will no doubt be the perfect last hurrah.
Friday, 3 pm: Arrival Aperitif
Enter by ferry if you can (a high speed ferry arrives on Nantucket every thirty minutes between the Steamship Authority or the Hyline, leaving from the Cape, New York, or New Bedford), which offers a panoramic view of the island from Great Point to Madaket as you enter and passes by the idyllic Brant Point lighthouse as it enters Nantucket Harbor. But if you’re a bit further than ferry distance, ACK from the air works beautifully, and cheap, 45-minute flights from Boston and New York City make their rounds on Cape Air as well as new flights from Charlotte and DC from American Airlines. The ferry puts you in town, while you can Uber or taxi from the airport into town, sandwiched between Surfside and Nobadeer beaches.
Check into any one of Nantucket’s signature cedar-shakes-with-white-trim B&B’s in town, like the Ship’s Inn, Barnacle Inn, or the Carlisle, all at the top of Main Street, for a get-to-know-the-hoteliers experience in a 17th century house (Nantucket, founded in 1629, boasts the largest number of 17th-century homes per mile in the U.S.). But if you’re feeling a more cocktails-and-cornhole-on-the-lawn vibe (or even just a view of Nantucket Harbor), try the Nantucket Hotel or the White Elephant, conveniently located a block away from the Steamship Authority (White Elephant can also meet you at the port and collect your luggage).
If charcuterie on the ferry didn’t make it onto your itinerary, walk head directly to aptly-named Straight Wharf Restaurant, situated at the end of the wharf where the Hyline ferry docks. Charcuterie and a rotating menu of tapas, like warm goat cheese and asparagus smeared on toasted baguette drizzled with balsamic, will clear any inkling of hungry grouchiness. But if the late summer Nantucket sun is making you swelter beneath your slacks, head to the Gazebo Tavern just across the patio from Straight Wharf for one of their famous mudslides, the alcoholic ice cream beverage that creates in-body air conditioning.
7 pm: Step to the Sunset
Most hotels and B&B’s offer complimentary bicycles (they’re the way to see the island), so when you finish at the Nantucket Boat Basin hit the cobbles with a light beach picnic (White Elephant and Ship’s Inn pack picnics, complete with rosé, right into your bike basket) and head to Steps Beach, one of the most famous beaches on the island for sunset viewing. Cheers to the clementine and lilac pastel sky, the wind in the rustling seagrass, and the dark magenta roses lining the path as you descend—Steps deserves the hype. When stars start to peek through the violet sky and the moon rises above the dunes, pedal back to town to prepare for your evening.
9 pm: Prerogative in Proprietor’s
When dressing for dinner at Proprietor’s, think dinner party at your friend’s summer house—and when you arrive, request seating upstairs in an utter jewel box of gem-colored wallpaper, patterned tablecloths, and mismatched china adorning the tables, all aglow with the flicker of candles and fresh flowers in mercury glass vases. And the family-style menu is no less impressive: Friendly to both sharing and pocketbooks, it rotates weekly based on fresh harvests from Nantucket’s own Bartlett Farm. For two, order four to five dishes (all similarly priced) and pop a bottle of wine as the plates start rolling: From bluefish focaccia to tomato, burrata, watermelon, and mint salad, no dish will disappoint.
10:30 pm: Ice Cream Amble
The Juice Bar remains one of the busiest ice cream stands during the high season, and though in mid-July the after-dinner line wraps well around the block, the wait is well worth it—though in the fall, no one waits. Sample the daily flavor, like coffee cake or strawberry wedding cake, but if you’re feeling indecisive, you can’t go wrong with a scoop of green monster (a favorite among Nantucket children that mixes chunks of cookie dough in mint ice cream) in a hand-rolled waffle cone and dipped in rainbow sprinkles.
For post-dinner perambulations, head to the wharf just at the end of the street near the Steamship Authority to study the rippling moonlight. At night, Nantucket is a harbor full of mercury glass, and for dazzling stars without the light pollution, walk around the corner to Brant Point Lighthouse, where you can view the Milky Way and every inch of sky is dotted with light.
Saturday, 11:00 am: or, Brunch
There’s no need to hit the town early with a late sunrise and lingering Grey Lady mist, so sleep in and hit or, The Whale for brunch, a brand new spot on island that earned high praise in its first season. They do light and casual best: from the daily doughnut to avocado toast and asparagus salad, or, The Whale makes the most out of a late summer bounty.
12:00 pm: Pack Provisions
Get your bills ready at this cash-only sandwich stand on Straight Wharf at the bottom of Main Street, where you’ll stock up for an afternoon at the beach. Provisions specializes in original sandwiches like the Turkey Terrific, Sassy Farmer, and the Mantucket. All are winners (spring for Portuguese bread made by Something Natural bakery, an almost-sweet white bread that can only be found on island). Pair it with a Something Natural tea or lemonade and hit the cobbles by bike; by now the beaches are warming up.
1:15 pm: Sweater No Sweat
Late in the Nantucket summer when the weather has almost turned cool but the sea breeze hasn’t died yet, you’ll need to pick a downwind beach out of the wind for the warmest possible day. The beautiful thing about Nantucket beaches is that out of 82 miles of coastline, most beaches are open to the public, so picking a beach is really just determined by the wind and how far you’re willing to bike.
Pack a sweater just in case of chilly wind (Skinny Dip’s Ellsworth and Ivey “Nantucket” sweaters will do), and if there’s a southerly, bike toward the Nantucket Sound to Dionis Beach, with panoramic views of the island reaching from Madaket to Great Point—on very clear days you can even see the little white toothpick signifying the secluded lighthouse. If the breeze is filling from the north, however, bike to Madequecham, a beach marked by a secluded cove of rustling white pines. If you must end your beach sojourn with ice cream, bike to the island’s eastern village of Siasconset, known as “the family beach,” for minimal surf and possible seal sitings. Polish off your beach day with ice cream at the ‘Sconset Market and pick up anything from pepper jelly to cherries at this proclaimed “fancy grocery”—it’s not rare to catch clerks slow dancing behind the counter to Frank Sinatra as they replenish the grocery’s supply of fresh scones. Too tired to peddle back into town? The Wave, Nantucket’s bus system, stops in ‘Sconset every 30 minutes, and with a $2 fare, you and your bike can hitch a ride back into town.
7 pm: Get Nauti
The Nautilus own the moniker of “most famous restaurant on Nantucket” for a reason, and after Labor Day, you won’t be waiting on the sidewalk when reservations open jockeying for a spot on their list. With influences from Japanese street food and Spanish tapas, Chef Liam Mackey’s dishes are worth it at any size or prize—small plates made for sharing could make up a meal, while larger parties can order one of the “table feasts” that could include a whole roast peking duck. Steeped in New England seafood tradition, tapas like the lobster tostada and yellowfin tuna lettuce wraps cannot be missed.
And the fun doesn’t stop with the food—even seasoned pros need to have a look at the eclectic, locally inspired drink menu with cheeky names like “Ack Nauti” and “That’s a Lot of Dong” (its price is listed in the namesake Vietnamese currency at the end of the description). But for a good time with a larger party, order a porron, a secret concoctions where patrons order only an alcohol base. The drink itself comes in a glass vessel reminiscent of a genie’s lamp, and crowds from Nantucket college kids to Elin Hilderbrand all enjoy the folly of pouring the delicious drink into the mouths of friends.
11 pm: Back of the Backbar
Ventuno Restaurant is one of Nantucket’s classics, but at night its vine-wrapped back patio is transformed into Backbar, a dive bar for the older crowd on island to get sloshy. Beat the drag of spilled drinks and sticky floors by heading upstairs into Ventuno’s almost-secret wine bar, where drinks come in glasses instead of plastic and you sure won’t find people stumbling into the bushes. It’s far and away the best wine on Nantucket—everywhere from Napa to Argentina to France is represented.
12:30 pm: Not Your Typical Club
Head back to Main Street for Club Car, where a piano bar has for the first time ever been made classy. Think New Orleans street car rumbling down St. Charles, but add a bar serving top-notch cocktails and a piano in the caboose. With Nantucket locals arm in arm singing cheesy piano bar classics like “Tiny Dancer” and “American Pie,” even if you’re a few nauti dogs in at this point (Club Car’s aperol answer to vodka and lemonade), it’s a night you’re not soon to forget.
Sunday, 10 am: Every Pressing Moment
Though Lemon Press café on Main is infamous for its expensive fair, the inventive smoothies paired with healthy cooler items like lemon meringue overnight oats make it worth the stop in. Sit on a bench outside while you eat, and then sip your smoothie as you stroll down the main drag. Stop at Erica Wilson for perfectly curated women’s fashion that brings Paris and Milan seamlessly to island time, with items like Roller Rabbit collaborations and their signature sky-blue Nantucket Island medallions. For the traditional island clothing experience, visit Murray’s Toggery Shop, where tailors still fit men in their “Nantucket Reds,” faded red canvas pants that are hemmed to the tops of penny loafers and waist bands are embroidered with initials in sail flags. This time of year your pants will be tailored after lunch, so walk over to Fresh, the liquor store-cum-sandwich shop that churns out everything from poké bowls to BLTs, all while thumping disco music from behind the stacks of Fishers Island Lemonades.
Take your lunch down to the wharf and dock walk for a little bit in the Nantucket Boat Basin, gandering at some yachts that charter for more than $900,000/week. Then take a look out at the harbor, filled with classic wooden yachts and day racers (many designed by H.H. Herrschoft), including a fleet of Allerions, the classic boat of Nantucket.
As the sharpness of the sea breeze signifies an approaching winter while you step back on the ferry or plane, you’ll be sure to savor the last few moments of summer like biting into the last summer peach: a twinge of sadness at the end, but the overwhelming perfection that took all summer to refine.
