Our NYC Pop-Up is open! Learn more

Icon Close

36 Hours with The Grey Lady: Weekend Guide to Nantucket

Icon Share

SHARE

Advisor - Kathryn Brennan
Curated By

Kathryn Brennan

  • Beaches

  • Weekend Getaways

  • Nantucket

  • Summer

Advisor - 36 Hours with The Grey Lady: Weekend Guide to Nantucket
Curator’s statement

To some, Nantucket is THE see-and-be-seen hot spot during the summer months, but your time on this idyllic island can be as busy or as agenda-free as you like. Nantucket is the definition of picturesque. It is the perfect getaway for those looking to do just that — get away from the hustle and bustle and enjoy the magic of a beautiful island while staying stateside.

The Fora Difference

Book with Kathryn to access exclusive perks and experiences on your trip.

Icon Travel Perks
Killer perks

Free upgrades, spa credits and more—we got you

Icon Recommendations
Personalized recs

Customized travel planning for your style

Icon Inside Knowledge
Insider knowledge

Expert advice from people who’ve actually been there

Where to stay in Nantucket

Unlock perks by contacting Kathryn to book your trip.

Things to do in Nantucket

Views from the ferry of Brandt Point Lighthouse

While late June through mid-August is Nantucket's peak season, my favorite times to visit are a warm May day or late August/early September, when most others have headed back to school. Christmas Stroll, which takes place the first weekend of December, is also an experience not to miss. Here is how I would spend 36 hours here, sans car, regardless of the season:

  • Friday: Hop on the high-speed ferry out of Hyannis, arriving in time for an al fresco lunch at Tree Bar, outside of Queequeg's. Stroll the cobblestone streets for some post-lunch shopping. My favorites include Mitchell's Book Shop, The Skinny Dip and Blue Beetle. Hop on the Cisco Brewery shuttle and grab a cold drink while enjoying live music, followed by dinner at Ventuno. Squeeze in for a nightcap (and optional sing-a-long) at Club Car.

  • Saturday: Begin your day with a stop at The Lemon Press for breakfast and coffee, and then spend the morning at the beach—either by walking to Jetties Beach or taking the shuttle to Surfside Beach if you need a bit more waves. In the afternoon, rent bikes and trek out to Madaket to get a sense of the quieter side of the island. The fish tacos at Millie's are memorable! Optimize your people-watching with dinner at Lola 41 and after-dinner drinks along the water at Cru.

  • Sunday: Grab a pastry from Born & Bread and take your bikes out to 'Sconset. Still sore from yesterday? Go with the town shuttle. Meander through this village, enjoying the bright florals brushed against the Nantucket grey exterior of the seaside cottages. Enjoy a sandwich from Sconset Market on the beach before heading back into town. Savor your mudslide from The Gazebo before heading to catch your ferry.

Places to eat & drink in Nantucket

Cisco Brewery, located inland and offering beer, wine, and spirits

  • Lemon Press - Cold brew, avocado toast, healthier fare

  • Black Eyed Susans - Heartier breakfast options located right in town

  • Tree Bar at Queequegs - Lobster rolls, fish & chips, al fresco dining

  • Cisco Brewery - Local beers and rotating food trucks

  • Millie's - Cold beers, fresh seafood, and front-row seating to the Atlantic Ocean

  • The Nautilus - Highly regarded dinner option but tough to grab a table—plan ahead!

  • Cru - A hot spot in town facing one amazing yacht after the next. Great for lunch or dinner.

  • Ventuno - Lively Italian restaurant centrally located in town

  • The Juice Bar - Homemade ice cream and waffle cones. Need I say more?

Need to know

Nantucket's pristine landscape and quaint ambiance are essential to enjoying a quintessential New England summer. In addition to the recommended properties noted above, home rentals through Fora are also available—please reach out to learn more! While summer is going to give you the best chance for all the outdoor excursions, it is also the busiest. Consider the shoulder months or the holidays as well for your Nantucket travels.

Advisor - Kathryn Brennan

Travel Advisor

Kathryn Brennan

Get in touch with Kathryn

Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.

You can expect a response from Kathryn within 1–2 business days. You’ll also be subscribed to our traveler newsletter (you can unsubscribe at any time).

For more inspiration and insider recommendations, visit our Nantucket page.

We use cookies to enhance the user experience. Read our Privacy Policy here.