Roland Bello

As part of a new series, Travel + Leisure is exploring America one three-day weekend at a time. Here’s what to do on a quick trip out to Nantucket Island.

Ellie Storck

Eighty-two miles of pristine coastline, untouched dunes, and some of the East Coast’s finest seafood bring beach-goers to Nantucket every year. Head 30 miles out to sea to dine on the freshest catches of the day, explore downtown's pre-Civil War homes, and soak up the sun in one of the oldest whaling towns in New England. Nantucket has amazing attractions for every seaside traveler—here's how to see it all in one long weekend.

Day One

When you step off the ferry from Hyannis (you can travel via either the Hyline or Steamship Authority), head straight down the docks to Broad Street and grab an iced coffee at a local favorite, Island Coffee Roasters. Make your way into town to the hotel where you’ll be staying for the next three days: the historical, centrally located Jared Coffin House (also on Broad Street). The three-story mansion dates back to the 1800s, when it was built by one of the island’s most affluent ship owners, Jared Coffin. The structure is one of the only ones on island that survived the Great Fire of 1846, and the hotel now offers visitors a taste of charming Nantucket history with comfortable, modern accommodations.

After dropping your bags, make your way through town down to Provisions on the South Wharf for a sizeable sandwich—a favorite is the Turkey Terrific. From there, cross the docks to check out the many waterfront shops. Stop into the Skinny Dip, a new clothing collective that features a mix of high-end, emerging brands with a nod to New England and local surf culture. Head around the corner to one of Nantucket's top-tier antique and local art dealers, East End Gallery on Old North Wharf.

Take a few hours to explore historic downtown Nantucket: Stop by the Whaling Museum to have a look into Nantucket’s past, and see the 46-foot-long sperm whale skeleton that was found on the shores of ‘Sconset in 1998, which is on display in the museum. Walk into the Nantucket Atheneum, the island's local library, and then weave in and out of the many boutiques, galleries, and cafes that line the cobblestone streets. A few must-sees: Murray’s Toggery Shop and Nantucket Looms on Main Street; Isobel and Cleo and Toujours Midi on Centre Street, and Nantucket Bookworks on Broad Street. Grab a milkshake at the old-school Nantucket Pharmacy on Main before resting up at the hotel.

Related: Nantucket Travel Guide

If you decide you've had enough shopping and want to get to the beach, Jetties Beach and Steps Beach are just a quick bike ride from town (you can rent bikes from several shops close to the hotel).

In the evening, walk toward Jetties Beach for drinks and dinner at Galley Beach, a classic Nantucket waterfront restaurant. Sit outside on the wooden deck overlooking the boats coming into the harbor while sipping a cold glass of rosé. Enjoy local fare like pernod-scented escargot with melted leeks, tomato garlic-butter, and pimenton pastry; and truffle-butter-poached two-pound lobster with local corn from Nantucket’s own Bartlett’s Farm.

Day Two

Grab a low-key but hearty breakfast at Black Eyed Susan’s on India Street, and then head to Young's Bike Shop on Broad Street to rent a jeep. Drive out to Cisco Beach where the sand is hot and the surf is lively. If you’re feeling up for it, opt for a surfing lesson with Nantucket Island Surf School—the trailer is always parked at the top of Cisco Beach in the parking lot.

After a day of sun and surf, drive around the corner from the beach to Bartlett’s Farm to take in the island’s local bounty—fresh flowers, produce, baked goods, and more. Cisco Breweris located right next door, so after you’ve finished shopping at Bartlett’s, drive down to the brewery for Nantucket’s finest craft beer (they also make wine, cider, and various liquors). The brewery is very dog-friendly, and there is usually a raw bar (167 Raw) and a couple food trucks—we like the overstuffed lobster roll from Millie’s.

When you get back to the hotel, walk into town and enjoy a seafood dinner a little off the beaten path at Sayles, located just outside of the main part of town (a walkable distance from the hotel). Order the fried bay scallops and a cup of clam chowder and eat out on the deck (or down on the harbor beach) while watching the boats bob up and down at their moorings.

After dinner, head to the South Wharf for a drink at Straight Wharf or Cru, both of which draw a lively crowd, then take an evening stroll down the docks to look at the boats.

Day Three

Start at Petticoat Bakery on Centre street for the best spinach and cheese croissant you'll ever eat, and a refreshing iced coffee. Today, it’s time to explore the farther reaches of the island. Head east out of town, toward the rotary and down Milestone road. Take in the sights—windswept trees, lighthouses in the distance, stretches of pristine golf courses. Your first stop: Siasconset (referred to as Sconset by most). This historic little village is its own designated town on the island, and is known for its distinct, hydrangea-clad white homes on the steep cliffs overlooking the ocean.

When you arrive, check out Sconset Market and pop into Claudette’s for a sandwich—you can't go wrong with the meatloaf. After you’ve had your fill of exploring the narrow streets and the beach, make your way to the edge of Sconset to look at Sankaty Head Light, the iconic red and white lighthouse on the eastern edge of the island.

Next, head down Poplis Road, past elegant homes with widow walks and lazy dirt roads that lead to the waterfront. If you're traveling with little ones, Quidnet Beach is a good stop to make—more often than not, it's very quiet, not busy, and an ideal beach combing spot. Spend an hour or so soaking up the sun, walking the shoreline, and perhaps spotting some seals. This beach is conveniently located right next to Sesachaha pond, which is a perfect swimming hole for little ones. (There is a small parking lot here, but parking along the road is perfectly acceptable, too.) 

Take the afternoon to explore the island by car or hole up on the shore. If you're looking for places that are great swimming spots and more likely to have a crowd, check out Surfside, Nobadeer, or Fisherman's beaches. Just before the sun goes down, drive west out to Madaket beach for a sunset walk. 

Make your way back to town and drop the car back at Young's, then sit for dinner at the Nautilus (make sure you call ahead for a reservation, especially on weekends). Some must-try small plates: to start, order the tuna poke, and for sharing, ask for the Peking duck feast, which serves up to four people.

After dinner, have a drink at the Club Car—depending on how late it is, you may find yourself gathered around the piano with everyone inside the bar singing late into the night. It's just a quick walk back to the hotel for some shut-eye before your morning ferry back to the mainland. To keep track of upcoming Nantucket events, check out the calendar at Nantucket.net

For more long-weekend itineraries in America's best vacation destinations, click here.

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