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The Perfect Weekend Getaway: Nantucket From Boston

Our new series on weekend road trips aims to inspire you for what's to come as we slowly return to travel.

Covid-19 Disclaimer: Make sure to check the status of the states, regions, and establishments in which you’re planning to visit prior to travel. Many regions continue to see high infection rates and deaths, while many states and counties remain under varying stay-at-home orders. Those traveling from areas with high rates of Covid-19 should consider avoiding travel for now in order to reduce spread.

Once one of the busiest whaling ports in the world, Nantucket is now an exclusive getaway for the uber-rich who prefer to stay under the radar. The island, 30 miles off the coast of Massachusetts, is also extremely popular with day-trippers from Cape Cod who spend the day exploring, then reluctantly catch the last ferry back to the “mainland,” already mentally planning a longer trip. And who can blame them? On Nantucket, there’s plenty to love.

Its Native American name means, “land far out to sea,” and a visit to Nantucket truly is an escape from the norm. Expect tidy New England-style cottages, cranberry bogs, historic lighthouses, and nary a chain store in sight. It also has miles of unspoiled beaches, a growing number of stylish boutique hotels, and a surprisingly sophisticated dining scene.

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From Boston, it takes a little over an hour via MA-3 South, to reach Hyannis. The Hy-Line and Steamship Authority ferries depart from Hyannis on Cape Cod. The traditional ferry is a little over two hours, while the high-speed ferries can get you on-island in an hour. The CapeFLYER train departs three times a week in summer from Boston’s South Street Station and arrives in Hyannis two and half hours later where you can catch free shuttles to the ferry terminal.


Your first glimpse of Nantucket’s cutesy harborside town is on the walk from the ferry pier to your hotel. You’ll want to immediately start strolling the storybook historic district—throwing photo after FOMO-inducing photo up on the ‘gram—so drop your bags at Greydon House, a posh 20-room inn, and start pounding the cobblestones.

Wander amid streets lined with former sea captains’ gray-shingled homes that now house boutiques, bistros, and B&Bs. On Centre Street, climb the bell tower of the white-steepled First Congregational Church for gorgeous harbor views. Meander over to Main Street, where you can pop into beloved stalwarts like Mitchell’s Book Corner, Nantucket Pharmacy with its old-timey soda fountain, and Murray’s Toggery Shop (we dare you not to leave without buying a pair of “Nantucket Reds” pants or shorts). Before a power nap back at your hotel, stop by the always-busy Juice Bar for a Crantucket waffle cone (vanilla ice cream with chocolate-covered cranberries).

Photo by Andrew Wolff on Unsplash

Nantucketers like to dress for dinner; so don’t be shy about looking sharp. Book a table at CRU, a trendy seafood restaurant right on the harbor. It’s all about the raw bar here: Slurping freshly shucked oysters and sipping rosé champagne at an outdoor table as the sun starts to set over the yacht-filled marina is a sublime on-island experience. Still raring to go? Order a craft brew at The Rose & Crown, a local fave with live music and karaoke nights.


Black-Eyed Susan’s is an island institution that’s known for its breakfast (and its long lines). Order the signature sourdough French toast topped with cinnamon pecans, but don’t linger too long, you’ll want to catch your island tour with Gail’s Tours. Gail Nickerson is a seventh-generation Nantucketer and knows the island like the back of her hand. The hour-and-a-half van tour takes you through the charming village of Sconset, with stops at Sankaty Head Lighthouse and the Old Mill.

Back in town, change into your swimsuit and flip flops, because it’s time to hit the beach. Rent a bike to pedal to south shore strands like Surfside (a three-mile ride) or Cisco Beach (a four-mile ride), popular with surfers. Madaket, famous for its sunsets, is on the far western end of the island and best reached via car or taxi. Before heading out, stock up on gourmet sandwiches like curry chicken salad on home-baked Portuguese bread at Something Natural. And a few of their giant chocolate chip cookies are a must.

On the way back, join the “après beach party” at Cisco Brewers, a mid-island brewery that also houses Nantucket Vineyard and Triple Eight Distillery. Amid live music and food trucks, chill at one of the communal picnic tables in the beer garden with a Whale’s Tale Pale Ale or a Sankaty Light lager, chatting up both locals and tourists. You could easily miss your dinner reservation (it’s been known to happen) but you’ll want to get back for a meal at The Proprietors Bar and Table.

Photo by Benjamin Rascoe on Unsplash

This India Street spot, housed in a beautifully restored historic building, has a modern farmhouse decor complete with wood-beamed ceilings and Mason jar light fixtures and a global small plates menu. You can’t go wrong with the Thai pork belly or Nantucket Bay scallop crudo, and try a few of the Prohibition-era cocktails. Keep your buzz going in the cozy downstairs 1840s Whaling Bar within the Brotherhood of Thieves restaurant.


Nantucket is oozing with maritime history, so after a cup of coffee and freshly baked chocolate frosted donuts at The Downyflake diner, spend the day immersing yourself in it. Give yourself plenty of time to explore The Whaling Museum. Housed in a former 1847 candle factory, highlights include a 46-foot sperm whale skeleton that washed ashore on Sconset’s Low Beach in 1998 and impressive collections of scrimshaw (the art of engraving images on in ivory; typically whale teeth) and rattan-weaved Nantucket lightship baskets.

The permanent exhibit Tragedy of the Essex, tells the story of the ill-fated Nantucket whaleship Essex, which in 1820 was attacked by an enraged sperm whale deep in the then-uncharted waters of the Pacific Ocean. The boat sunk and the shipwrecked crew of 20 then set out on small whaleboats—only eight survived. It was, of course, this tragedy that inspired Herman Melville, who had once worked aboard a whaler, to write Moby Dick. To learn more about the Essex, read In the Heart of the Sea by Nantucket resident Nathaniel Philbrick.

Cap off your visit to Nantucket with a lobster roll from the Straight Wharf Fish Store. Eat it down by the pier, the same location where those whaling ships once departed from, and as you wait for the ferry to bring you back to reality, start plotting your return.


Raising the bar for inns is the elegant Greydon House, which opened in 2016 and is designed by NYC-based design firm Roman and Williams. Its restaurant Via Mare, from the Ventuno team, serves Venetian-inspired small plates. A few doors down is 21 Broad, a stylish boutique with bright contemporary interiors. The year-round Nantucket Hotel & Resort is an island classic complete with a pool, spa, and beach shuttles. And if you’re looking for an exclusive experience, stay at the Wauwinet, an adults-only hideaway on the island’s remote northeast corner with two private beaches and the award-winning Topper’s restaurant.


Peak season is summer when you can take full advantage of the beaches but fall and spring are lovely too, with the latter known for its popular festivals including the Food & Wine Festival in May and the Nantucket Film Festival in June.