How to Spend a Perfect Weekend on Nantucket According to InsideHook

All the best things to do, see and eat on “The Little Grey Lady of the Sea” by Lauren Wicks for InsideHook.

Originally published on InsideHook.

I’ve gotten to travel to some pretty amazing places as a travel writer, but there’s just something special about the island of Nantucket, with all its history, natural beauty and folklore. Unlike the Hamptons or Palm Beach, this iconic vacation destination for the one-percenters doesn’t feel snooty or pretentious in the least. While you definitely can’t travel on the cheap here, you’ll be pleasantly surprised by the unassuming, laid back vibes — though you will feel like you’ve stepped into a vintage J.Crew catalog. 

How to Get to There

Nantucket is easier to get to than one might think. You can fly commercially from Boston year-round for as cheap as $50 if you plan ahead, while there are also plenty of commercial flights from cities like New York, D.C., Chicago, Charlotte and Philadelphia from the end of May until October. Additionally, there are a variety of options for those interested in private charters anywhere from Maui to Miami. 

Otherwise, you can do like the locals and hop on a ferry from Hyannis, New Bedford or Martha’s Vineyard, and there are also ferries from New York City in the summertime. Definitely snag a ticket on one of the high-speed ferries, if possible, as they’ll get you to the island in about an hour. Check out Nantucket Ferries to find the best option for you. If this is at all confusing, reach out to the concierge at your hotel who will be able to offer plenty of guidance on getting to and from the island as smoothly as possible from wherever you are in the world. 

Where to Stay

Those looking for something a bit more youthful and design-centric should check out Greydon House, a stunning B&B designed by Roman & Williams (of Ace Hotel New York and Le Coucou fame). Greydon House is perfectly seated just off Main Street and has an ambient Italian restaurant, Via Mare, with a killer drinks menu.

What to Do

Whether you’re visiting in spring, summer, or fall, there’s no shortage of activities to enjoy on the island. What’s great about Nantucket is that the island moves at a slow, refreshing pace while offering plenty to do for those who are a bit more antsy. A visit (or five) to Main Street is a must for checking out the shops, cafes and historical landmarks that are the backbone of the island. Be sure to stop into Murray’s Toggery to snag some authentic Nantucket Red duds before heading to Miacomet or Siasconset (also spelled Sconset) for a round of golf.

Speaking of outdoor activities, you’ll likely want to pick up a bike for the weekend to ride from point A to B each day. White Elephant Resorts offers complimentary bike rentals, but Nantucket Bike Shop is a good stop on your way in as well. The shop will also offer plenty of guidance on the best biking routes to the island’s 10 beaches and anywhere else you’re looking to go. Boating is also a popular way to get around, catch the day’s lunch or simply get your day drinking on in style as there are plenty of antique tugboat and yacht rentals. 

History buffs and fans of Herman Melville should save some time for perusing the Nantucket Whaling Museum, which is actually way cooler than it sounds. However, if you really want to get the Moby Dick experience and are on the island in season (June through September), book a whaling history tour with Shearwater Excursions.

Where to Eat and Drink

Nantucket’s culinary scene is an excellent representation of the island itself: there are plenty of chic, waterfront restaurants to see and be seen at as well as an abundance of quirky roadside attractions and beachfront taco shacks that highlight the island’s laid-back charm. 

Cisco Brewers is a favorite stop of locals and tourists alike, not only for its creative local brews (wines and spirits, too!) but for the incredible food trucks lining the brewery and its unbeatable atmosphere. Pick up a tray of lobster tacos, local oysters or a few slices of pizza while you sip a Gray Lady and listen to local jam bands and soak up the Nantucket sun. Though a bit of a trek to Madaket, Millie’s is another great laid-back dining location that offers killer seafood dishes and sammies morning, noon and night, plus a legendary rum punch. 

If you’re looking for a more upscale dining institution, Galley Beach and Straight Wharf are favorites for dinner with water views — just be sure to book your reservations ASAP. Brant Point Grill at the White Elephant is another Nantucket favorite that offers elegant dining alfresco, while Òran Mór offers festive libations and elevated local fare in a moody, intimate setting at a former historic home. Culinary enthusiasts who really want to go out with a bang should book a table at American Seasons or Chanticleer for an unforgettable dinner. Oh, and don’t miss a trip to The Juice Bar for the island’s most beloved ice cream scoops. 

Beyond Cisco Brewers, Millie’s and Òran Mór, there are plenty of great watering holes on the island. Check out The Proprietors for innovative cocktails and The Club Car for a lively late night with live piano. (Make sure to swing by Handlebar Cafe the next morning for the island’s best espresso fix).

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