A weekend guide to Nantucket

Just 30 miles off the coast of Massachusetts, Nantucket grew as a a major whaling port in the mid-1800s. Today, it’s easily accessible by air as many major airlines have resumed nonstop flights from major cities on the Eastern Seaboard, including New York and Washington, D.C. (Although pay attention to schedules as there are fewer in the offseason, which is most of the year outside of spring and summer.)

And while spring and summer are peak seasons with tourists—with the coastal weather making it an idyllic escape from most of the humidity drenched over the East Coast for months at a time—fall really is the best time to visit.

During the cooler months, starting as soon as the first week of October, the population drops, the ocean is still warm, and the weather is ideal for enjoying outdoor activities, such as biking, sailing, lobstering, and strolls to nearby lighthouses along 82 miles of coastline and dramatic cliffs. (And it rarely snows here compared to the mainland.)

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From the walking trails of Sanford Farm and Masquetuck Reservation to the grassy lands of Tom Nevers and the Pitch Pine Barrens, more than 50% of Nantucket is under permanent conservation and much of the protected land is available for exploration. (And whatever your preconceived notion is of Nantucket’s size, it’s going to be much larger than you realize, so consider renting a car, bringing your own on the car ferry, renting a bike, or booking a tour guide with a car as there are many long distance between major sites and villages.)

Throughout the year in the town center of Nantucket, most of the local boutiques that line the cobblestones remain open, and lines are shorter at popular ice cream parlors, restaurants, and breweries.  Harvest season also kicks off for the Nantucket Bay scallops as well as the annual family-friendly Cranberry Festival, celebrating the island’s signature fruit. 

Suffice to say, if you’re itching for the full fall experience with small-town charm, Nantucket should be on your bucket list.

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Where to go

Great Point Lighthouse: You might assume if you’ve seen one lighthouse, you’ve seen them all. But on Nantucket, that’s just not true. The island has many original lighthouses (some a few hundred years old), which have played an important role in the island’s history and economy given its position in the Atlantic Ocean. It might seem counter-intuitive, but the lighthouse shines brightest (for your photos) when late afternoon sunlight hits, so plan accordingly. It is difficult to get to this lighthouse, however, and you should not attempt to drive on your own given its position on a long sandbank. But you can arrange a tour here (and other spots on the island) through The Trustees of Reservations in Massachusetts.

Endeavor Sailing : There is so much to be seen by foot, bike, and car, but one of the best ways to tour Nantucket is by sea. The Endeavor, a United States Coast Guard certified vessel, is the longest operating sailing charter on Nantucket, led by Captain James Genthner, a.k.a. Captain Jim, for the last 35 years and counting. You can book a daytime or sunset sail, and yes, you can bring drinks.

Whaling Museum: Housed in a former candle factory, this is a must-visit spot for anyone who wants to learn about the history of Nantucket, with tours highlighting both the indigenous communities that first lived on the island and the whaling industry. Originally founded in the 1930s, the museum underwent a major renovation and expansion in the 2000s, resulting in very modern, elegant layout, hosting numerous well-preserved art, clothing, and other artifacts, as well as a 46-foot sperm whale skeleton hanging from the ceiling. Museum guides stress that they are not attempting to paint a heroic picture of the island’s role in the whaling industry, but it is intrinsic to understanding Nantucket’s economic history. Whale oil, especially, became very valuable in the 18th and 19th centuries—before electricity—as it could be used to make more efficient—and critically, odorless—candles for everywhere from homes to street lamps to lighthouses. The success of the whaling industry in Nantucket—before the California gold rush attracted many of these would-be entrepreneurs out west—made the island the fifth richest community in the world at one point in time.

Historical walking tour: Central to Nantucket’s everlasting charm is its architecture, and even before landing or sailing up, you’ll notice just how uniform the architecture is, from homes to hotels to gas stations to Fedex or UPS outposts. You can learn more about why this is while also seeing some of the most historic homes on the island (at least those that survived the great fire of 1846), including those that belonged to historical figures like abolitionist and suffragist Eliza Starbuck Barney and astronomer Maria Mitchell.

Cisco Brewers: This might be the happiest place on the island. What could be better than outdoor drinks (including locally made craft beers and wines as well as cocktails made from local spirits) in the sunshine with wood-fired pizza (or a lobster roll from the food truck), live music, and plenty of dogs mingling with their humans. (Yes, this place is very dog-friendly.) You can take a 10-minute taxi from the town center, or you can opt to get here by bike. (Just plan accordingly on how to get home, so drink and ride responsibly.)

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Where to eat

Topper’s:  Located at the Wauwinet hotel, the onsite restaurant serves a full menu for breakfast, lunch, and dinner. Topper’s itself is named after the owners’ beloved dog, who you might see on colorful postcards, notebooks, and other knick knacks in the gift shop. And even though Topper’s is casual (there is no dress code beyond “casual chic”), it is consistently ranked among the top restaurants in New England and a repeated recipient of Wine Spectator’s “Grand Award.” The seasonally inspired menu is simple, but hits the spot with a focus on local produce and seafood. Highlights from the menu include the Retsyo Oysters, sourced 300 yards from property, and a beet and endive salad with blue cheese, walnuts, and cranberries, which are the pride and joy of Nantucket farming.

Brant Point Grill: The White Elephant’s Brant Point Grill is a staple restaurant on island, with an enviable view of the harbor from both indoor and outdoor seating. The restaurant also has a standalone full bar inside with plenty of high-top tables and standing room, with HDTVs mounted to the wall for watching the games of the day. And while the bar is best known for its famed Lobster Bloody Mary, consider the Espresso Martini as well. But the restaurant is very popular for rehearsal dinners and weddings, so call in advance to book a reservation (and sure they are open to guests when you want to go).

Lemon Press: This is the best spot for vegetarians and vegans (or anyone looking for a healthy, refreshing meal) with lots of fresh-pressed juices, smoothies, açai bowls, salads, and grain bowls. (But this being Nantucket, where seafood is king, there are options for everyone, including dishes with salmon, mussels, and shrimp.) This is also a popular brunch spot, open early on weekends, with an eclectic menu of wines and spritzes.

Walter’s: Quite possibly one of the best (if not the best) sandwich spots on the island, Walter’s is known for its generously sized sandwiches and lobster rolls. This one is takeout and standing-room only, so you could take your sandwich and eat alfresco on the boardwalk across the street while overlooking the harbor or take it home for a late-night snack as it is open until 2 a.m.

Nantucket Tap Room: An honest bistro where you’ll find tourists mixing with locals. This is a solid choice for dinner with hearty portions as well as a full bar. (And you’re more likely to meet locals sitting at the bar while watching a Celtics or Patriots game.)

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The Wauwinet: Truly, this can be a spot where you come to get away from it all. Built in 1875, the location is a standout—with access to two private beaches—one on the ocean and one on the bay. Situated on the northeast end of the island while bordering the idyllic Coskata-Coatue Wildlife Refuge, the 32-room Wauwinet is the island’s only Relais & Chateaux property. An adults-only escape, the hotel offers an ambiance of storybook romance, especially abundant in the property’s individual cottages scattered around the grounds. The hotel has also been busy hosting wedding after wedding this year, many of which are entire buyouts of the property for the wedding party and their guests, so book well in advance. And when you’ve had enough time to relax, the hotel offers a number of guest activities, such as the free use of Priority bicycles and the onsite tennis court as well as bookings for surfcasting, sailing, paddle boarding, kayaking, cooking classes, and, of course, lobstering.

Jared Coffin House: If you’re looking for a hotel with an early American feel and located in the town center, this is your home base. The three-story mansion has more than 40 guest rooms and suites, some of which have already experienced a very modern and luxurious renovation, and the rest of the rooms are scheduled for updates as well. Note that part of the hotel is open seasonally: during the high season of the summer months as well as the first week of December, known as Christmas Stroll, which is when you should visit if you really want to play out your own holiday movie experience.

The Cottages and Lofts at the Boat Basin: Even the hotel managers agree that this can be best described as the cross between a hotel and a long-term Airbnb rental. Many of the multi-bedroom suites and cottages here are rented for weeks at a time (with repeat guests year after year). And notably, it is very pet-friendly. And when we say pet-friendly, we really mean it. The hotel estimates 25% of its guests bring a pet with them, and this is probably because the property’s pet policy is very generous. Dog owners can bring up to two dogs—of any breed, any size—with them. But that’s not all. Yes, cat owners and their cats are welcome, and the cottages have also hosted hamsters, pigs, and even ducks. This is a hotel that really understands that pets—of any shape or size—are family, too.

White Elephant: There are many lovely properties on Nantucket, but this might be the largest and most luxurious given how many amenities there are available, including access to a spa, a private beach (year-round), a pool (open in summer), an onsite restaurant and bar with room service, a library (with a daily wine and cheese hour), and a 24-hour fitness center. On the outside, it exudes Nantucket’s iconic architectural elegance with grey shingles and white trim. But inside, the rooms have been renovated and decorated to modern standards (with a dash of coastal grandmother here and there). White Elephant also has the most diverse options for accommodations from guest rooms and suites to multi-bedroom (and multi-story) cottages and residences. Just a short walk from the main town center on Nantucket, many of the hotel’s suites face the harbor with some on the ground floor that allow you to walk straight out from your suite to the garden.