24 Hours in Nantucket, MA

by Sabrina Smelko


Nearly 30 miles into the North Atlantic (and seemingly a world away from the Massachusetts mainland), today’s city guide brings us to the enchanted enclave of Nantucket Island. Once the whaling capital of the world, Nantucket hasn’t changed all that much from its whaling heyday — at least, architecturally speaking. Absent of a single traffic signal, neon sign, big box store or restaurant chain, the waterside downtown village has remained paved in century-old cobblestone that, at least according to island legend, once served as stabilizing ballast on trade ships.

“From the minute you take your first step onto Nantucket, you’ll understand why its original Native American inhabitants named it a word meaning ‘faraway island’,” the writer of today’s city guide, Andrea E. McHugh, remarks. Despite its reputation for being a lofty and expensive place to visit — especially in the summer months — today, Andrea is showing us how “you don’t need a trust fund to enjoy the very best that ‘The Little Grey Lady of the Sea’ has to offer.” Sabrina

Morning Visits

Early riser: If you’re the type to be up and out before your brood, grab a hot cup of joe at The Bean on India Street where you’ll find everything from organic coffees to roasts using beans that spent a month aging in barrels from nearby Triple 8 Distillery. Pick your poison and walk the docks of the Nantucket Boat Basin where in the warmer months, you’re likely to find upwards of 200 boats bobbing as the sun rises beyond the horizon.

9 am: Start the day off at Black-Eyed Susan’s, a not-so-secret breakfast hotspot in the center of town that’s too small for its loyal fanbase but worth the wait. Chances are you’ll have to give your name to the hostess and bring along some patience (tip: grab stools at the counter if available). The creaking wood-framed screen door that smacks the doorjamb with every entry and exit, wide open windows attempting to cool the “cozily” seated crowd, and southern-style cheesy grits might make you forget you’re still in New England.

10 am: Burn off some of those blueberry pancakes by sauntering about the shops along what’s called Petticoat Row, a section of Centre Street (between Main and Broad Streets) where, during the 1800s, when many of the townsmen were off at sea, women ran the shops and small businesses there. (Beware of some buckled bricks there, too — they may not officially date as far back as the 18th century, but they’ve certainly settled like they do).

11 am: Whether or not Moby Dick was on your middle school required reading list, a visit to the Nantucket Whaling Museum will give not only history of the barbaric industry that built this island, but the stories of the island itself. Don’t miss the jaw-dropping panoramic views from the rooftop observation deck.


Afternoon Visits

12 pm: At just 25 square miles, Nantucket it the perfect size to explore by bike. Young’s Bicycle Shop is the oldest bike shop on the island (and also rents bikes for kids, bikes with child seats, covered trailers for little ones in tow, and more) and the crew there will hook you up with helmets, locks and all-important bike trail maps. They’ll also dish on their favorite local hangouts if you nudge ’em a bit.

YOUNG'S BIKE RENTAL cr William DeSousa-Mauk

Photograph above: William DeSousa-Mauk

12:30 pm: Take a short trek out to Galley Beach, a chic, sand-in-your-toes spot, for a little alfresco champagne overlooking the sea.


Hop back on your bike and head about four miles inland to family-owned Bartlett’s Farm, the oldest on the island. Perched atop a hill and surrounded by fields of vegetables, flowers, annuals and perennials, the expansive farm market may just be Nantuket’s best kept lunch secret. With freshly made meals daily, you’ll find a selection featuring farm fresh ingredients (as you might expect) in addition to organic meats, gourmet cheese, just-caught seafood, artisanal breads, from-scratch soups and desserts.

BARTLETT FARM cr William DeSousa-Mauk

Photograph above: William DeSousa-Mauk

2:30 pm: Continue experiencing local flavor on your way back into town with a stop at Cisco Brewers, home to a brewery, distillery and winery. Once a tiny, bucolic, beer-brewing campus, today you’ll find a bustling place with libation-lovers from all walks, milling about. Taste the array of Cisco brews and Triple 8 Distillery’s vodkas, liqueurs, scotch and bourbon; as well as Nantucket Vineyard’s wines. Inside spaces meld seamlessly with outdoor ones and a dog or two may cross your path. Just be sure to check any uppity attitude at the door — here your hacky sack skills carry more street cred than your hedge fund.

CISCO BREWERY (31) cr William DeSousa-Mauk

Photograph above: William DeSousa-Mauk

Evening Visits

4 pm: Head back into town and explore the wealth of mom-and-pop shops and galleries. My favorite might just be Current Vintage, a vintage clothing shop meets wine and cheese shop — basically one lovely, tasteful trifecta. For the men, I baptize thee into Murray’s Toggery Shop, the birthplace of the ubiquitous Nantucket Reds. A retail institution for more than half a century, here’s where you can officially get your prep on.



7:30 pm: Nantucket is as rich in history as it is in culinary talent, so your biggest decision during your stay may just be where to unwind for dinner. I’m loving one of the newer additions to ACK’s dining scene: The Proprietors Bar & Table.



Couple and co-owners Chef Michael and Orla LaScola earned an enviable reputation at the helm of the acclaimed American Seasons but opened this gem, defined as a “culinary ode to the well-traveled palate” in 2013. Using ingredients predominately sourced from area farms, growers and artisans, the menu celebrates global cuisines and invites a shareable dining experience with a host of small plates. The wine list is equally an international affair, highlighting small producers from near and far.

Nightcap: Who would have thought that a tiny, retrofitted railway car would be quite the hotspot, but The Club Car is a true throwback, right down to the piano player tickling the ivories. You won’t be disappointed: order a classic dirty martini and belt out some tunes.

THE CLUB CAR, MAIN ST, NANTUCKET cr William DeSousa-Mauk (1)

THE CLUB CAR, NANTUCKET (2) cr William DeSousa-Mauk

Photograph above: William DeSousa-Mauk

Suggested For You


  • The Club Car was the hangout on the show Wings, that took place on Nantucket.

  • You Nailed It….First landed on this island in 1972 ,Much has changed since then,Most of the places you speak of were something else back then…..Still you did an awesome job,all the places you mention are worth going to,many things to do and mutch to SEA…….Ps.You forgot 56 UNION That place Rocks…..Things to do on your next 24 hours…..WJB

  • Loved reading this. Brought me back to the Island that truly saved my life in 1977. These plans sound perfect and I hope that I can get back there some day. My dream is to live there but I would cherish a week or two!

  • I’m just coming across this post now. Last October my husband and I were engaged on Nantucket, at the light house! There is onebox store there, stop and shop, but all the other charm us still there. Thats a recent change to the island. We frequently ate at The Bean, the have gf options, and tried a good number of restaurants there. We ended up being stranded there for one 1 more night because of winds and rough seas. It was fun coming across this after visiting the island. Rechnized so much information. My husband loved the whaling museum. They gave an interesting lecture/ q&a that we attended. Can’t wait to go back!!!