36 Hours on Nantucket Travel Guide

When to Go

Late summer/early fall is one of our favorite times to be on this gem of an Island 27 miles out to sea. The light is beautiful, the water is warm, and the crowds are gone.

How to Arrive

By ferry is always a great way to get a real feel for going away. You are transported to another time and place. Or come by Air on Cape Air or Jet Blue from NYC /Westchester or Boston or try score a seat on one of the new small private airlines.

Where to Stay

In town, The Faraway and Greydon House are two lovely options. Or opt for an Air BnB and stay in a cottage on the Wharf.

How to Get Around

Foot, Car, Bike or Boat or all of the above.

Get out on the water - take a sailboat ride or the harbor launch to view Nantucket from the perspective of the original whalers.

Take a Jeep or bike and head out on the sand roads to Ladies Beach behind Bartlett Farm or the Miacommet beach dunes where one of the last standing wooden fish houses stands.

Day 1: Friday: Arrival and Check in

Walk up cobblestoned Main Street and take in the historic houses and gardens. Lunch is fresh and delicious at Pip and Anchor where all the food locally sourced from within a 100-mile radius. 

Continue taking in town, stroll down to the wharves along Easy Street and visit all of the unique shops from our Nordic home store fare at Eleish Van Breems Home to hip fashions at Erica Wilson to great jewelry at Susan Lister Locke and grab wine for later at Current Vintage.

Photo: Matt Kisiday

Have dinner at the newly renovated Straight Wharf restaurant designed by Workshop/APD. 

Gaze at the stars at the Maria Mitchell Observatory, then go out and have a dance at the Chicken Box.

Day 2: Saturday

Wake up and have breakfast at Lemon Press on Main Street who have the best juices and muffins.

Then check out Sylvia Antiques and Nantucket House Antiques for authentic island crafts, history and antiques. Raphael Osana Auctions is a treasure trove and always changing and has previews on Saturdays.

Nantucket House Interior 

Take a bike and ride out to Sconset! Get sandwiches at Claudette’s, walk the bluff and check out the charming village the old Casino and tiny cottages.

Sunset and feet in the sand at Galley Beach. Drinks at Via Mare and Dinner at Sister Ship or Cru - try the local oysters! Pocomo are delectable!! Late night singing at the Club Car.

Day 3: Sunday

Early risers get coffee at then breakfast at Black Eyed Susans. Or if looking for lighter fare then walk down street and have Coffee and Breakfast at Born and Bread.

Take a walk down to Brant Point Lighthouse or if looking for longer trek go out to Ram’s Pasture which has fields, flowers, and birds galore.

Grab sandwiches and salads at Bartlett Farm and drinks at Cisco Brewery, then head to Ladies Beach or take in a sail with the guys from the Lynx or the Endeavor.

Finish your day with Ice cream at Juice bar.

Rainy Day activities

The Whaling Museum is world class and not to be missed. Drive and see a Lighthouse you have the choice of three: Brant Point, Sankaty or Greater Light. And don't forget to visit the Lifesaving Museum.