A Perfect Nantucket Weekend

If you’re dreaming of cobblestone streets, fresh lobster rolls, and sunsets by the sea, a weekend in Nantucket is the perfect getaway. Whether you fly into Boston or Cape Cod and hop the ferry across, the island feels like a world away as soon as you arrive. Here’s how to make the most of a long weekend on ACK.

Day One: Arrival & Exploring Downtown

Once you’ve made it across by ferry or flight, grab a taxi or shuttle and head to the Beachside Hotel to drop your bags. It’s just a quick ride from the ferry, and from there you’re ready to hit the town.

Lemon Press

Start the trip with something light at Lemon Press-a cold brew, smoothie, or avocado toast is the perfect way to fuel your day. From there, wander through the charming shops downtown. Stop into Murray’s Toggery (famous for Nantucket Reds), Perch, Current Vintage, Nantucket Looms, Vis-à-Vis, CJ Laing, and Eye of the Needle. Each shop feels like a little treasure box, and browsing them is half the fun.

Lunch

For lunch, head to CRU on the harbor for oysters, lobster rolls, and a glass of bubbly. With the boats bobbing just outside the windows, it’s as Nantucket as it gets. Afterward, swing by the Juice Bar for a cone of their homemade ice cream-a local legend. Try the chocolate and Oreo in a homemade waffle cone! 

If you missed any shops, now’s the time to circle back. It’s also worth stopping into Provisions to pick up a sandwich to tuck away for later. In the late afternoon, grab a ride out to Cisco Brewers, a favorite hangout with beer, cocktails, and often live music. It’s the perfect spot to unwind before the evening.

Dinner at Nautilus

After freshening up at the hotel, enjoy dinner at Nautilus, where small plates and seafood are given a creative twist. End the night at The Chicken Box, Nantucket’s iconic music bar, where locals and visitors alike dance late into the night.

Day Two: Books, Bluff Walks & Sunsets

Born & Bread Bakery

Start the morning at Born & Bread, a bakery and coffee shop known for its pastries and hearty breakfast sandwiches. Then make your way to Mitchell’s Book Corner, one of Nantucket’s beloved bookstores. This is where you’ll find events like Elin Hilderbrand’s book signings. Pick up your copy, line up early, and enjoy the chance to meet Nantucket’s own “queen of beach reads.”

After the signing, grab a quick bite at Provisions or a nearby café, then head out to Siasconset on the east end of the island. The Sconset Bluff Walk is a scenic path along the cliffs, lined with charming cottages and sweeping ocean views.

No trip to Sconset is complete without a stop at the Sconset Market for cookies or ice cream, and if you have time, enjoy a cocktail or a light bite at Summer House Beachside Bistro, which sits right on the sand. Before heading back to town, pause at Sankaty Head Lighthouse for photos — it’s one of the island’s most iconic sights.

Drinks & Dinner

Back in town, refresh at the hotel and then enjoy pre-dinner drinks at The Gazebo, famous for its mudslides and lively harborfront energy. For dinner, you have two options: head to Millie’s in Madaket for fish tacos and an unforgettable sunset on the west end, or stay downtown for sushi and cocktails at Lola 41 or Yoshi. Either way, you’ll end the night with a great meal. If you’re not ready to call it quits, enjoy a nightcap at Club Car, live music at Gaslight, or a final moonlit stroll along Straight Wharf.

Day Three – A Sweet Send-Off

Roastd Nantucket

On your last morning, stop at Roastd Nantucket for one more coffee and pastry. Then take a stroll to soak up the island’s charm before you leave — whether that’s Brant Point Lighthouse, the soft sands at Steps Beach, or one last round of souvenir shopping downtown. If you can squeeze it in, grab one more cone from the Juice Bar or a sandwich from Provisions for the ferry ride home.

Head Home

Check out of your hotel, hop in a taxi, and make your way to the ferry or airport. With sea breezes in your hair and saltwater on your skin, you’ll already be planning your next trip back to this little island paradise.

Have you been to Nantucket? I’d love to hear your favorite spots! Drop a comment below so we can keep adding to the bucket list!