How to Have the Perfect Weekend in Nantucket

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I’ve had the opportunity to travel to some pretty amazing places as a travel writer, but there’s just something special about Nantucket Island, with all of its history, natural beauty, and folklore. Unlike the Hamptons or Palm Beach, this one hundred percent iconic vacation destination doesn’t feel pretentious or pretentious at all. While you certainly can’t travel cheap here, you’ll be pleasantly surprised by the laid-back, unpretentious vibe – even though you’ll feel like you’ve stepped into a vintage J.Crew catalog.

Sun loungers at Wauwinet

The Wauwinet

How to get there

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

Alternatively, you can do as the locals do and hop on a ferry from Hyannis, New Bedford or Martha’s Vineyard, and there are also ferries from New York in the summer. Definitely buy a ticket on one of the high-speed ferries, if possible, as they will get you to the island in about an hour. Check out Nantucket Ferries to find the best option for you. If this confuses you, contact your hotel concierge who can give you lots of tips for getting to and from the island as easily as possible, wherever you are in the world.

Bed and Breakfast Greydon House

Bed and Breakfast Greydon House

Douglas Friedman

Where to stay

Whether you’re looking for a historic B&B downtown, a luxurious retreat away from the crowds, or an Instagram-worthy spot at every turn, the island has no shortage of beautiful accommodations. Those looking for a place with all the amenities or a family vacation should look to the picturesque White Elephant Nantucket, which is widely considered one of the most luxurious stays on the island. The resort offers an impressive range of accommodations, from classic hotel rooms to garden cottages and lofts, as well as excellent restaurants, a beachfront spa and many curated experiences to get the most out of your trip. (think: yacht charters and free self-driving BMWs). to get around town)

If you’re looking for something a little more romantic and away from the main drag, sister property The Wauwinet is an idyllic place to spend the weekend. This hotel sits on the other side of the island, offering a taste of what Nantucket was like before Ivy League alumni and industry titans began spending their summers here. ‘Golden age. Plus, you simply can’t beat the golden hour views of Wauwinet from its beachfront lawn.

Those looking for something a little more youthful and design-focused 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 located just off Main Street and has an atmospheric Italian restaurant, Via Mare, with a killer drinks menu.

White Elephant Residence

White Elephant Residence

White elephant

What to do

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

Speaking of outdoor activities, you probably want to take a bike for the weekend to get from point A to point B each day. White Elephant Resorts offers free bike rentals, but Nantucket Bike Shop is also a good stop on your way. The shop will also offer lots of advice on the best cycling routes to the 10 beaches on the island and wherever else you want to go. Yachting is also a popular way to get around, grab the day’s lunch or just spend the day drinking in style, as there are plenty of vintage tugboat and yacht rentals.

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

water white elephant

water white elephant

White elephant

Where to eat and drink

Nantucket’s food scene is a great representation of the island itself: there are plenty of upscale waterfront restaurants to see and see, plus an abundance of quirky roadside attractions and beachfront taco shacks that showcase the island’s laid-back charm.

Cisco Brewers is a favorite stop for locals and tourists alike, not just for its creative local beers (wines and spirits too!) but for the amazing food trucks that line the brewery and its unbeatable atmosphere. Pick up a platter 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 sunshine. Although a bit far from Madaket, Millie’s is another great casual dining spot that offers killer seafood dishes and sammies morning, noon and night, as well as a legendary rum punch.

If you’re looking for a more upscale dining institution, Galley Beach and Straight Wharf are favorites for water-view dining — just be sure to book your reservations as soon as possible. Brant Point Grill at the White Elephant is another Nantucket favorite that offers elegant al fresco dining, while Òran Mór offers festive libations and fine local fare in an intimate, moody setting in a historic old house. Food enthusiasts who really want to go out in style should book a table at American Seasons or Chanticleer for an unforgettable dinner. Oh, and don’t miss a trip to Juice Bar for the island’s most beloved scoops of ice cream.

Beyond Cisco Brewers, Millie’s and Òran Mór, there are plenty of good 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 stop by Handlebar Cafe the next morning for the best espresso on the island).

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