The Itinerary

What to Do With 48 Hours in Nantucket

What to Do With 48 Hours in Nantucket

Break out the Breton stripes and break in your topsiders. It doesn’t get more nautical than spending a few days in Nantucket.

Every summer, Bostonians and New Yorkers pour out of their hot cities and head to Nantucket. Ask them why, and most will tell you about lobster rolls and sailing. The real reasons to visit? It’s the forest-green hydrangeas blooming in their natural habitat, and climbing over miles of sprawling dunes to reach untouched beaches. So much of the fabled island remains as wild as it was centuries ago, and you can see it all—even if you only have 48 hours.

Day 1


2 PM. Arrive in the early afternoon. Feel that breeze on the ferry dock or the tarmac? Nantucket enjoys a unique Oceanic climate, making summer days on the island up to 10 degrees cooler than the mainland.

2:30 PM. Drop your bags at Life House. With contactless check-in on the Life House app, it’s like getting home and going straight to your room. While you freshen up, play “Cool Cat” by Queen on your in-room Marshall speaker to get in the island mood.

3 PM. Explore on two wheels. Cycling is the best way to get around the island. Head to Young’s Bicycle Shop, open since 1938, where you can rent bikes by the hour, day, or week.

3:30 PM. Pedal to Jetties Beach. On the way, be on the lookout for black-eyed Susans, a native Nantucket sunflower. Stay on the sandy beach for a few hours, and make the most of the popular restaurant with a spacious deck where you can order lobster rolls and frozen drinks.


7 PM. Get ready for dinner. Back at Life House, switch on the Marshall speaker and queue up “Lady Magnolia” by Piero Umiliani to set the mood for the evening. Before you head out, stop in the garden to take in the sunset.

8 PM. Dine by candlelight. You don’t have to go far for dinner. Turn the corner to reach American seasons, a rustic restaurant that offers a list of more than 500 American-made wines and seasonal fare.

9:30 PM. Find a not-so-hidden bar. Behind Ventuono’s Italian restaurant is Ventuno’s Back Bar. While it feels hidden away, it’s one of the most popular spots in town where you can sit outside under a trellis of local Nantucket flora. Order from the menu of specialty cocktails and Italian wines.



Day 2


8 AM. Practice the art of breathing. Rise with the sun and cycle through town to The Yoga Room, where you can take an outdoor vinyasa flow class.

9:30 AM. Have breakfast with the locals. On your way back to Life House, stop at Black-Eyed Susan’s, a cozy, cash-only breakfast spot.

11 AM. Explore Nantucket’s whaling history. Immerse yourself in the whaling culture that inspired Moby-Dick. Whether you’re a Herman Melville fan or simply want to learn more about the profession of Captain Robert Calder, the original owner of 10 Cliff Road, the Whaling Museum is the place to go.

1 PM. Set sail one of the most recognizable wooden yachts in the world. Straight from the pages of Hunter S. Thompson’s The Rum Diary, The Blue Peter has raced in regattas from the UK to St. Tropez to Antigua since she launched in 1930. Join Captain Mat Barker aboard the 65-foot sailing yacht for a charter around Nantucket, complete with a lunch of lobster rolls and Quinn Rosé.


8 PM. Head to dinner in the heart of town. The Proprietor’s Bar & Table pays homage to Nantucket’s whaling history and celebrates the palate of its well-traveled sailors. Take a journey with dishes like seared halloumi, cold sesame noodles, and red lentil falafel, which bring a global flair to the restaurant’s vintage plates.


Day 3


10 AM. Swing by Provisions. Order breakfast, and pick up some sandwiches for your last trip to the beach.

10:30 AM. Pedal to Steps Beach. Climb the wooden steps over grassy dunes to reach this famous beach.

1 PM. Bring a piece of Nantucket home with you. Paper aficionados will love Heidi Girvin’s stationery shop, Parchment. From Mr. Boddington to Shinola, the brands in stock will have you penning letters like it’s the 19th century. At Nantucket Looms, a weaving collective since 1968, buy a hand-loomed blanket, throw, or rug to always have a touch of the Nantucket aesthetic at home.

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WHERE TO STAY

Life House, Lower Highlands

rooms starting at $149/night

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Life House, Collins park

rooms starting at $149/night

Visit

Life House, Nantucket

rooms starting at $149/night

Visit