The Nantucket Weekender: How to Make the Most of the Gray Lady in 48 Hours

November 12, 2019

Thirty miles off the coast of Massachusetts is the tiny Atlantic island of Nantucket. Popularly known as the Gray Lady because of its dense foggy nature, the island attracts hoards of visitors to its cobblestone downtown streets and dune-lined beaches. But when you’re trying to squeeze in a visit between the work weeks, it can feel rushed. We have what you need to know about planning the ultimate Nantucket weekend.

Everything You Need to Know About Planning a Weekend in Nantucket

Indulge in all the best restaurants, explore picturesque lighthouses, and fall in love with this magically untouched piece of New England paradise. Only have the weekend? Don’t fret. Plan strategically, and you’ll have plenty of time to see all of the top spots on the island. 

  • Indulge in the Finest Food

Nantucket is coated with five-star, farm-to-table, you-can-only-find-this-in-Nantucket, restaurants. It’s a foodie’s paradise. From fresh Atlantic lobster to tangy calamari to honey-glazed duck breast, there’s a little something for everyone. 

But wait. There are only three meals in a day, totaling six meals for the weekend. (if you catch the latest ferry, that is) With a bucket list of restaurants to visit, how do you make time for them all? Come with us for an exclusive Nantucket progressive dining tour.

  • via mare greydon drinkAll Good Nights Start With a Cocktail From Via Mare

One of the trendiest new(ish) spots in town, Via Mare, is connected directly to Nantucket’s stylish boutique hotel, Greydon House. The restaurant offers an extensive and creative drink menu with seasonal options and ingredients. Pair it with a cicchetti-sized oyster plate, and hang out in the dim-lit, Bohemian-style bar for the perfect start to your night.

  • Experience Authentic Italian at Ventuno

If there is only one thing you need to remember about Ventuno, it’s this—get the calamari

Everything on the menu here is the best of the best, but the Fritto Misto is like none other. The perfectly fried dish is bursting with lemon butter flavor and tastes as if they pulled it out of the ocean minutes after ordering. The Polpette, aka authentic Italian meatballs, are satisfyingly portioned and doused in warm tomato sugo. Say it with me—yum.

  • Make Your Reservation at The Nautilus

It’s hard to talk about Nantucket dining without mentioning the Cambridge Street classic, The Nautilus. This one requires a little bit of planning—you’ll want to call ahead to reserve a table—but it’s worth the work. 

One word—splurge. Order tapas staggeringly. A few of our favorites are the creamy Lobster Tostada, the Japanese-style Sichuan Dumplings, and the Steamed Pork Buns complete with crispy pork belly.

  • Satisfy Your Sweet Tooth at Oran Mor

Oran Mor is the perfect way to end your Nantucket date night. Open the sea-worn door and float up the candle-lit stairwell to the quiet, intimate eatery. From the cozy nooks to the faintly candle-lit wooden mantle, this spot is straight out of every romantic Blockbuster. 

“Just the dessert menu, please.” That’s the only verbiage you’ll need at this spot. There are few things more difficult than choosing a dessert from Oran Mor. During the summer, we recommend the fresh strawberry dish, Pavlov’s Response. The meringue-based dessert is light and fluffy, topped with sweetly poached rhubarb, and basted with lemon balm. 

Don’t have a sweet tooth? Try the Cheese N Biscuits. The tiny made-to-order, flakey biscuits are paired with house-made apple butter and Cabot clothbound cheddar makes for the flawless blend of sweet and salty. Once the napkin is on the plate, make the short stroll, just steps, back to Greydon House.

  • Get Your Weekend Transportation

The only way to see Nantucket is on two wheels. But there are a few things you need to know first. 

    • nantucket steps beachCheck Out Your Five-Speed at Young’s Bike Shop

Just across the street from Greydon House is Young’s Bike Shop. The employees there are friendly and make the process easy and quick so that you can spend more time on the trail. Reserve it for the weekend or the day. Once you’re through, hitch it up behind the shop and drop the key in the dropbox. 

    • Choose Your Route

The island itself is just a mere 15 miles long and three miles wide, so biking it is doable for even the least experienced cyclist. The folks at Young’s will supply you with a bike map and rules of the road, but here are some of the most effective ways to make the most of your bike trip. 

      • To Sankaty Lighthead: Take Polpis Road up to Baxter Road. Loop around Baxter through the tiny beach town of Siasconset. Then head back to town via Milestone. 
      • To Children’s Beach and Brant Point Lighthouse: Head down South Beach Street. Children’s Beach is a quick quarter of a mile down the road. Turn right at the light onto Easton and the road dead-ends at Brant Point. 
      • To Steps Beach: Travel down Beach Street until it turns into Jefferson Avenue. For the perfect Insta-op, take Cobblestone Hill up to Lincoln Avenue. Take a right, and you’ll spot the signs for Steps just around the bend.

Remember—it’s the journey, not the destination, so slow down and enjoy the nostalgia of the island.    

  • Greydon HouseStay in the Heart of Downtown Nantucket at Greydon House

There is no better spot to stay for a short stay on the island than Greydon House. It’s the first hotel you’ll come to when unloading from the Steamship. It’s steps from the best bike and Jeep rental spots. And it’s centrally located near all of Downtown Nantucket’s premier shopping and dining spots. And they don’t stop with location.

The 17-room boutique hotel is sophistically decked-out in ornate Greek Revival decor blended exquisitely with classic Nantucket flair. From the reclaimed, dark Chestnut floors to the hand-painted Dutch and Moroccan tiled, deep walk-in shower, Greydon House is truly one you have to see to believe. Book your stay in the Federal Suite and live like a local with a ground-floor, residential-style entrance. The suite boasts a pillow-top queen-size bed, a comfortable sitting area, and a bathroom almost too gorgeous to bath in.

Time flies. Let it linger a little longer in Nantucket this weekend.