Since we’ve already covered Martha’s Vineyard, this week we’re focusing on that rival Massachusetts island: Nantucket. Or, in the immortal words of Billy Joel, “We have charted a course to the Vineyard, but tonight we are Nantucket bound.” The omnipresent fog lends the island its nickname, the Gray Lady, and the ferry ride to Nantucket truly feels like a journey “into the mystic” (to quote another legendary songwriter, Van Morrison).

But you don’t need to be a fan of classic rock to appreciate Nantucket. This idyllic destination in New England appeals to nature lovers and cocktail drinkers alike. Though Nantucket is hailed as the anti-Hamptons, the scene at The Chicken Box can be just as debauchery-filled as anything you’ll find at the Memory Motel in Montauk.

This Nantucket versus Hamptons rivalry is captured in the Instagram feed @ackvshamps with the slogan “Where Do You Summer?” (and on the NVH prints for sale). While summer is unfortunately now over, venturing to Nantucket in the off-season is just as memorable. Fall is one of the most gorgeous times to visit the island, which is why we’re highlighting the Gray Lady for this edition of carless weekend travel. Read on for your guide to Nantucket.

Where to Stay

Beach house in Nantucket

One of the most beautiful destinations in New England, Nantucket is perfect for a long weekend any time of year. Flights to Nantucket can be risky due to the aforementioned fog, so we recommend booking a ferry from Hyannis, Harwich, or New Bedford. Who needs a private jet (or a Blade helicopter or seaplane) to fly into Nantucket (ACK) airport, when you can watch the New England coastline above deck while enjoying a cup of rosé or a Cisco beer? (More on that signature drink later.)

There’s even a Seastreak ferry that departs from New York City for the island, but be careful: People have been known to get seasick on the journey. So take a Dramamine and hope for the best. Though the Seastreak is seasonal, from May 25 to September 3, the Hy-Line Cruises and Steamship Authority ferry lines operate year-round from the Cape and Martha’s Vineyard.

Once you spot the Brant Point Lighthouse from the ferry, you know you’ve arrived. When on the island, Ubers from the ferry are plentiful, as are the beautiful views and endless beaches on the way to your final destination. As for accommodations, we recommend renting a house, especially if you’re traveling with a group of friends. Many owners rent their homes for portions of time throughout the year, and this is often your best option. Peruse Airbnb for a classic Nantucket-style shingled house (like the one pictured above).

If you’d rather enjoy the amenities of a hotel, we like The Pineapple Inn and Summer House India Street. The White Elephant Hotel is probably the most expensive, but the luxurious waterfront resort (with its cottages and spa treatments) is one of the poshest, most romantic spots on the island.

What to Do

Nobadeer Beach in Nantucket

Summer kicks off with the annual Figawi race over Memorial Day weekend (which is named after sailors who got lost in the fog during the first race in 1972 and wondered aloud in their Boston accents, “Where the f*** are we?”). This origin story may be local lore, but more than 40 years later, you and your friends may wonder the same thing while navigating downtown Nantucket on this notoriously busy weekend. You should plan on skipping the big holiday weekends during the summer if you aren’t interested in crowds.

Luckily, as we’ve mentioned, Nantucket isn’t just for summertime. The annual Christmas Stroll (held on the weekend of November 30 to December 2 this year) is a picture-perfect holiday experience, filled with carolers, hundreds of Christmas trees, and an abundance of cheer (and seasonal cocktails). In the spring, the Annual Daffodil Festival will be held April 26-28, 2019. The festival celebrates the end of winter with art shows, an antique car parade and, of course, the Annual Nantucket Daffodil Show.

But fall in Nantucket is, in our opinion, the best time of year. The beaches are slightly less crowded, though the ocean is still warm — or, warm for Massachusetts (if you’re a fan of the Caribbean, expect to freeze). The island colors come to life as the leaves change, and the crisp morning air is ideal for setting out on a long hike or bike ride (activities made for your Instagram feed).

Love being out on the water? Book a fishing charter with Bill Fisher Tackle, learn how to hang ten at ACK Surf School, or sign up for kitesurfing, wake-boarding, or hydro-foiling lessons at Next Level Watersports (they recently partnered with the Westmoor Club, a historic members-only club near Brant Point). Speaking of the open seas, before people were wearing whale pants on Nantucket, they were actually hunting for whales. Learn about the history of Nantucket at the Whaling Museum, and explore the fields and beaches around the village of Sconset for a glimpse into what this old whaling capital might have looked like before it became a popular tourist destination.

As far as beaches are concerned (it is an island after all), we recommend Nobadeer, Smith’s Point, Ladies, and Surfside. Drive on the beach at Nobadeer (pictured above) and spend an afternoon watching the planes fly by overhead. Nicknamed “Brobadeer,” this beach is one of the more popular on the island, so you’re likely to run into friends — or make new ones.

Eat lunch at Millie’s before heading out to Smith’s Point on Madaket Beach with a cooler of beverages and a fishing rod: Atlantic bonito start appearing in the surf in late July or early August. But you don’t need to be a fisherman to appreciate this part of the island — the path to the beach is dotted with roses in the summertime, and the sunrise at Smith’s Point is one of the most beautiful in the world.

If you’re visiting over the holidays, go to Smith’s Point at dawn on New Year’s Eve to greet the sunrise from one of the easternmost parts of America. To catch the sunset, you’ll want to be at the Great Point Lighthouse for one of the most Insta-worthy snapshots on the island.

Take advantage of the abundance of bike paths and explore the island’s beaches the old-fashioned way (AKA the way you got around before you had your driver’s license). Bike to Surfside Beach (and order lunch from the new Beach Shack and Taco Truck) or navigate the sandy dirt roads of the more secluded and rugged Ladies Beach.

Where to Eat and Drink

Bartlett's Farm in Nantucket

Ladies Beach is our personal favorite beach to visit, not only for its beauty but also for its proximity to Bartlett’s Farm (pictured above). The sandwiches at Bartlett’s are the perfect post-beach pick-me-up, ideal for fueling up before heading to nearby Cisco Brewers. A very popular scene in the summertime (with the long line to prove it), this brewery is a lot more laid-back in the off-season. If you grew up in New England and want to see everyone you ever went to high school with, go there on an afternoon and try to avoid the “Panic at the Cisco” — a potent mixture of claustrophobia and social anxiety.

Bartlett’s is also the best market to visit if you’re planning on having dinner in one night (many of the restaurants — though worth it — tend to be on the pricier side). Order one of the farm’s excellent homemade pies (and pesto spreads) before stopping at 167 Raw to pick up fresh fish or bourbon beef sirloin tips to prepare for dinner.

For breakfast on the go, order the (sinfully delicious) chocolate and sugar donuts at The Downy Flake. If you’re looking for a sit-down brunch, opt for Black-Eyed Susan’s, located right in the heart of town on India Street. Afterward, grab an iced coffee at Corner Table and explore the shops and restaurants. If it’s a rainy day, put your name in at Met on Main for lunch — though it tends to be busy, the cozy atmosphere was made for camping out at during a storm. And if your plans involve the beach, the pizza at Oath and the sandwiches at Fresh are both good options.

Want to splurge on a nice dinner out? Order the striped bass or scallops at Ventuno or sushi at Lola 41 (fish, unsurprisingly, is always a reliable choice here). The bar scene at both restaurants is pretty lively, so plan on staying for after-dinner drinks (and visit the bar out back at Ventuno once you finish eating). Cru is more Hamptons-esque (read: dinner is expensive), but the fun nightlife scene is definitely worth checking out.

Though it’s nearly impossible to get a table there, Nautilus lives up to the hype. The restaurant starts taking reservations at noon the day of, but if you’re unable to secure a reservation, try your luck at the first-come, first-serve bar. If you’re into tequila cocktails and small plates, then go to Proprietors (and order the Shishito peppers).

Now, onto where to imbibe. Spend an evening hanging out beneath the twinkling lights of Tree Bar (where there is actually a tree in the middle of the bar). This local favorite, located next to the restaurant Town, is more low-key than The Chicken Box or Straight Wharf (though they too have their charms).

For our next choice, we’re bringing it back to Billy Joel with The Club Car, a piano bar where a singalong to “Piano Man” is a rite of passage on a trip to Nantucket. Located in a retro railway car, the bar has a friendly, laid-back atmosphere and slightly older crowd — though all ages are known to partake in the revelry.

In terms of live music, The Chicken Box is an iconic institution in Nantucket. With an outdoor patio, live bands, pool tables, and a raucous dance floor, this bar is the very definition of debauchery. Located further from town than many of the other bars (which are walking distance from one another), The Chicken Box requires a certain level of commitment — and whether it be ordering a drink at the jam-packed bar, dancing near the front of the crowd, sticking it out in an endless line, or getting up on stage, we believe in you.

The Straight Wharf offers a similarly fratty vibe, though with less dancing. Luckily Cru, Straight Wharf, and the Gazebo are all right next to one another, so you can decide which atmosphere you prefer as the night goes on.

Or you can sidle up to the Gazebo on a Sunday afternoon and order a mudslide to pretend that Monday doesn’t exist. Just don’t be surprised if you run into like-minded travelers and miss your ferry. Nantucket may be a hard destination to get to, but it’s even harder to go bACK home.

What are your favorite spots on Nantucket? Tag us in your go-to spots on Instagram @BritandCo.

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(Photos via Tripp Schoff; featured photo via Getty)