How to Spend a Perfect 48 Hours in Nantucket
Welcome to the VERANDA Weekend Guides, where we show you how to make the most of 48 hours in one of our favorite destinations. This month we are featuring Nantucket, with guidance from Tuckernuck Cofounder Jocelyn Gailliot. Gailliot has been visiting Nantucket since she was just six weeks old and even got married on the New England isle.
"The moment you get on the island and gather with family and friends, you instantly feel like a kid again," Gailliot says. "You feel so connected to nature, history, architecture, and art here—in the best way possible—and as a result, everything feels so rich, and you feel so present. The food tastes better, the drinks flow faster, and you experience everything in much more carefree way. Life starts to move at a slower pace."
Below, you'll find Gailliot's favorite things to do in Nantucket. From the best places to stay to the tastiest bites, here's our guide to help you spend a fabulous weekend on the legendary vacation destination.
Friday Afternoon: Check In
Check in to the White Elephant, which underwent a complete renovation for the season. This iconic harborside hotel also recently partnered with Arhaus to outfit its outdoor spaces with custom seating in its signature blue shade. Beyond well-appointed furnishings, the hotel also offers a pool, world-class spa and complimentary beach cruiser bikes and cars (which make getting around the island a breeze).
Friday Afternoon
Swing by Rafael Osana Auction House to discover the latest antiques, artwork, and other incredible finds the local institution has to offer before the weekly auction begins Saturday morning.
“It’s a hidden gem,” Gailliot says. “A lot of New York dealers will come and shop here, and they have the most incredible local artists and furniture from estate sales. I’ve gotten tons of Wolly art, antique campaign chests, side tables, and local art from the sixties and seventies. It’s a great visit even if only to discover the local art and history.” She says brown furniture fanatics should especially make the auction house a must-see.
Friday Evening
You’re likely ready to eat after a day of travel. What better way to celebrate your arrival than a spritz at sunset?
“The Galley is a great restaurant with good drinks and sunset views,” Gailliot says. “The food is some of the best of the island, and it’s walkable from Greydon House.”
If you’re ready to keep the night going, you won’t want to miss an evening at the Club Car. Snag a quick rideshare, and immerse yourself in the live music and libations at the popular piano bar and restaurant.
Saturday Morning
Don’t sleep in too much because there’s a lot of ground to cover! Start your day off right with a smoothie bowl from local favorite Juice Press before popping in to bid at Osana. Or simply throw on your swimsuit and make a stop at Bartlett’s Farm for locally roasted coffee, baked goods, and breakfast sandwiches on your way to Cisco Beach for a day of sun and surf. Gailliot says you can also pick up delicious sandwiches at Bartlett’s on your way out to the beach if you’re looking to stay all day.
“Nantucket is an amazing island if you like to bike,” Gailliot says. "You can spend 48 hours on Nantucket without ever having to rent a car. The town spent the last decade on bike paths that connect the whole island.”
From there, you can charter a boat for a guided clamming or scalloping tour, take a surf lesson, or simply enjoy a good book to the sound of the waves crashing on the shore.
Saturday Afternoon
If you don’t feel like spending all of your daylight hours on the beach, there is plenty to do and see around Main Street. Gailliot says Nantucket is a shopper’s delight because it doesn’t allow any franchises on the island (except for Ralph Lauren), which means you’ll have access to one-of-a-kind boutiques.
Gailliot advises stopping into Gypsy and Erica Wilson for women’s clothes and renowned needlepoint work. Deemed America’s First Lady of stitchery, a trip to Erica Wilson is a must.
Murray’s Toggery is another institution in Nantucket, as it is home to the Nantucket Reds collection—an exclusive clothing line featuring a patented red fabric that’s frequently sported on the island.
There are plenty of afternoon pick-me-ups around the corner from Main Street’s best shops, like Lemon Press for grain bowls, the Nautilus for small plates, and Provisions for salads and sandwiches.
Saturday Evening
Gailliot says American Seasons is a must for foodies and anyone looking to get the most fabulous dining experience on the island.
“It feels very 'Nantucket' with the architecture, art, and vernacular,” Gailliot says.”It’s very historic New England. The food is a little esoteric, but it’s all really fresh. There are lots of farms nearby, and all the restaurants get food from there.”
Sunday Morning
Start with breakfast at White Elephant before checking out. From there, Gailliot advises taking a quick walk to historic Brandt Point Lighthouse, the second lighthouse built in Colonial America.
“The ferries pass by, and it’s a tradition for everyone to throw pennies there, making a wish to come back,” Gailliot says.
Before you leave the island, you must stop by Hadwen House. This spectacular manse was built in 1846 and is one of the most beautiful examples of Greek Revival architecture on the island. Pop inside to the museum and explore Nantucket's lightship baskets, decorative arts and historic maps from the island.
Afterwards, take a quick walk over to the Whaling Museum and check out the nine permanent and rotating galleries. There, you'll learn about the island's 400-year-old history through the thousands of art, artifacts and treasures on display (including a 46-foot sperm whale skeleton and a restored candle factory from 1847). Don't miss the gift shop on the way out for a chic souvenir to remember your trip to Nantucket.
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