Though I’m now embarrassed to admit it, our invitation to Nantucket felt confusing. The only preconception I had of the island were thanks to J. Crew magazines—and therefore the only mental pictures I could conjure up were of model types wearing “Nantucket red” (aka pink) polo shirts with popped collars on fancy boats. But alas, a google image search proved it to be beautiful place; plus, we’re always up for new experiences. So we accepted. And though we were somewhat uncertain of what to expect when we stepped off the boat, what we found in Nantucket genuinely surprised us. The very first thing I noticed? Not a single pink polo in sight.

Instead, our hosts–Suzanne and Wendy of Nantucket Bookworks–picked us up from the dock wearing Converse sneakers and dresses. They led us through Nantucket’s cobblestone streets, which are lined with cute restaurants and indie shops. Adding to the picturesque setting, the architecture is largely comprised of beautifully sun-and-sea faded buildings. Oh, and the cars: the impossibly cool, pristine vintage cars! Everywhere. Our entire trip was far more laid-back and artsy than we could’ve imagined. Turns out, you just have to know the right crowd.

Officially traveling for business, we were invited along to shoot an event for Paul of Sweet Paul Magazine; his partner James of the Phoenicia Flea also joined. Our hosts Suzanne, Joy and Wendy were the perfect team to curate our experience in Nantucket, kicking off our weekend with a little welcome party. Invitees were artists, designers and business owners of various trades: Randy at Cisco Brewers and Triple Eight Distillery, illustrator Jeanne Van Etten, chocolatier Ambrosia Nantucket, farmer/artist Michelle of Dancey Pants Disco, and knitwear designer Charlotte Hess of Isobel & Cleo–just to name a few. It was through meeting this group of artists, designers and business owners that we were able to experience the island through their perspective, and ultimately create this guide. No “Nantucket reds” required.

Though we got a lot of different recommendations, the locals all agreed on one thing: fall, especially the month of October, is the best time to visit. After Labor Day has come and gone, most tourists have their eye on different parts of New England. Hotel prices plummet. But during October, the water is still warm enough to swim on a nice day, and explore-worthy by foot or bike during what’s arguably the most beautiful time of the year.

There’s a few ways to get to Nantucket, the easiest of which is probably flying. JetBlue flights from JFK begin around $200 during low season, and only take about an hour. Another option is driving to Hyannis, MA and hopping on the Hyline Cruise ferry, which is about an hour ride for the 30-mile trip. Either way, once you’re in town, cabs, Ubers, and public transit are plentiful, so there’s really no need to worry about transportation once you’re on the island.

Where to Stay in Nantucket: A Literary Oasis in the Center of Town 


We stayed at The Second Story Loft, a three-bedroom apartment rental conveniently located on Broad Street. The two-story loft occupies the second and third floors of the building above Nantucket Bookworks; and its quite literally filled with books, guaranteed to inspire. Two large bedrooms have queen beds; a lofted bedroom has two twins. The kitchen is beautiful and equipped with modern chef-worthy amenities, well-equipped to handle dinner parties; a table in the living room seats up to ten people. During high season, guests at the Second Story Loft are surrounded by lively restaurants, museums, and charming shops. Off-season, it’s a peaceful, book-filled getaway with space to entertain.

Getting Outside in Nantucket: Beaches and Scenic WalksIMG_7618_RETOUCHED

Being an island, there’s a plethora of beaches in Nantucket, and every local has a different favorite. The two that came up the most were Steps Beach on the North Shore, and Cisco Beach on the South Shore. Steps is a popular choice because it’s an easy commute, at just a 1.5 mile walk or bike ride from town. Because its protected by the Nantucket Sound, the water is shallow, warm, and calm. It’s named after the hundreds of steps that lead down to the beach; it’s also said to have some of the best views of the North Shore on the island. At Cisco, it’s a different scene. The beach here faces the Atlantic Ocean, so waves are stronger and bigger, making a more adventurous swimming experience. It’s popular with surf crows too; surfboards, wetsuits, and stand-up paddleboards are all available to rent. Our group of friends opted for Cisco, which is also notable for its proximity to Cisco Brewers for a post-swim beer.

Nantucket is known for its historic and iconic lighthouses. The most accessible one from town is the Brant Point Lighthouse, which is impossible to miss on the ferry ride into Nantucket. It’s an easy walk from town and a great spot to watch the sunset. Further out, the Sankaty Lighthouse in Siasconsett was built in 1850 and offers some of the best Instagram-worthy shots on the island. You’ll need a car or bike to get there from its access point on Baxter Road.

Speaking of Siasconset–or “Sconset” for short– you’ll definitely want to make trek to this scenic part of the island. Visitors flock to this historic fishing village where some homes are over two centuries old, and little has changed since the 1700’s. The picturesque homes and low-roofed bungalows are nearly identical, with their shingled facades and brightly colored trims. In some parts, Sconset can feel more like an elaborate garden than a neighborhood; roses, vines and other flowers climb the sides of many homes here, complete with lush flower boxes and neatly kept yards. Plan to spend the afternoon wandering its winding streets, eventually making your way down to the beach. Don’t miss lunch at Claudette’s, where you can get a great sandwich and sit on the patio overlooking the main square. Located on the eastern shore, Sconset is 8 miles from the town of Nantucket. To get here, rent a bike for the day, or take the The Wave bus for $1. (Off-season visitors take note: busses end service after September.)

Nantucket has been an eco-tourism center long before the term was invented. Whale watching and seal cruises are quite popular, though if you must choose one, we’d recommend the whale watching. Half-day excursions can be booked through Shearwater Excursions. Though these adventures are rather pricey ($165 per person), the 1.5 hour trip to the best whale watching spot is an adventure in itself; plus, customers are guaranteed a sighting. Snacks and beverages can be purchased on the boats, which have a 35 person limit, so you won’t be rubbing elbows with other tourists the whole time.

The Great Indoors: Museums, Shopping, and a Culinary Center

Those who wish to explore the nautical heritage of Nantucket should check out the award-winning Whaling Museum instead. The museum is just down the street from the Second Story Loft, and housed in a restored 1847 candle factory. Highlights include a rooftop observation deck overlooking the Nantucket harbor, and the complete skeleton of a sperm whale.


Those interested in the culinary arts should check out the Nantucket Culinary Center, where a two-story demonstration space regularly hosts special events and classes. Events are hosted Chef Greg Margolis and a rotating roster of guest chefs, all of whom explore current food trends as well as the heritage of island farming and fishing. Check their website for a schedule of upcoming events.


Finally, the shopping is phenomenal in Nantucket. What we expected to be touristy knicknack shops were instead upscale surf, antique, art and design shops collections. Our favorite collection by far was at Nantiquet, whose collection of nautical antiques was right up our alley. Another swoon-worthy collection of home goods can be found at Bodega, and pretty much every booth at Nantucket Farmers & Artisans Market. Book worms should check out indie bookstores Nantucket Bookworks, or Mitchell’s Book Corner, whose selected curated selection includes stocks of titles in all areas, as well as extensive selections about Nantucket, whaling, and the island’s genealogy. Those looking to update their beachwear collections should check out Town Pool, The Skinny Dip, and Faherty. More refined is the beautiful knitwear collection at Isobel & Cleo, where designer Charlotte Hess creates her entire collection by hand in the space directly above her store. Ask to take a peek!

Where to Eat & Drink in Nantucket: A Beachy Brewery With Food Trucks, Seafood, and Farm-to-Table Restaurants


Despite being an island 30 miles off the mainland, Nantucket has great food and even its own farmers market. Though seafood is the main fare, there’s a wide variety of restaurants, take-out counters, seafood shacks, and even BBQ. First on the list, dinner reservations are recommended well in advance to try Nautilus, whose classic New England menu is updated with an Asian twist. It’s the hardest restaurant to get into on the island, so give them a call as soon as you nail down your getaway plans. Just as good, and slightly more laid-back is Proprietor, whose cocktails are reason enough to stop in (try to the smoky gin cocktail!)… but the food is outstanding as well. On the other end of the scale, we were able to try a variety of local fare as Cisco Brewery, whose backyard is packed with food trucks, with live music on weekends to boot. For something non-seafood, Backyard BBQ is a solid option and really close to the harbor for a post-meal stroll. Vegetarians will appreciate their roasted mushroom roll, which is prepared like a lobster roll with lemon aioli.

For breakfast, check out The Corner Table and take in the fresh Nantucket air on their large patio. Most food is already prepared, so their take-out style sandwiches, salads and soups are ideal for a quick bite. Items like hot sandwiches and oatmeal are made to order. For a more traditional brunch experience, try out Black Eyed Susans, a down-to-earth eatery whose inside resembles a diner. If it’s warm enough, ask for a seat on the back patio, where you’ll feel like you found your way into a garden. Just be sure to bring some dough for this cash-only spot.

For dessert or just a mid-afternoon pick-me-up, the Juice Bar has a wide variety of treats–but everyone goes for the ice cream. Especially during peak season, you’ll often find yourself in the middle of a line that wraps the building, but it moves fast and is worth the wait, especially for its unique flavors like cake batter, rum raisin, and ginger. If waiting in lines isn’t your thing, forego the ice cream and check out Ambrosia Nantucket, whose artisan chocolates are to die for. We tried her signature tree bark, made with toasted almond, saffron, and smoked chili on chocolate. Last, just as good is Small Town Girl’s handcrafted goodies like brittles, toffee, caramels, and marmalades. Don’t miss her at the Nantucket Farmers & Artisans Market!