The soul of Nantucket is one of fortitude and ingenuity. Landing on a shore over thirty miles from the mainland, its first settlers built booming industries from the ground up. Throughout its centuries of triumphs, Nantucket has become a luxurious, coastal haven. Strolling its sweeping beaches, traversing its winding bike paths, and witnessing the remnants of a bustling whaling industry, one can relax on this island rich with history, culture, and activity.

Journeying to the island can be accomplished by sea or air. The Steamship Authority and Hy-Line Cruises both offer year-round ferries from Hyannis to Nantucket, with the fast ferries arriving in about an hour. The Freedom Cruise Line, a seasonal fast ferry with easy parking, runs from Harwich Port. For transportation via air, Nantucket Memorial Airport offers flights from Boston, Hyannis and other nearby hubs.

Arriving on island, Steamship Wharf, home to the Steamship Authority, has all of the logistical amenities needed for an island adventure. Bike rental shops make it easy to find a fun mode of transportation. Also along the wharf are convenient spots for a quick bite to eat or an ice cream cone. Stop by Steamboat Pizza for a slice  to fuel you after the ferry ride, or for a refreshing treat, check out the famous Juice Bar to enjoy a homemade ice cream cone. 

The Hy-Line and Freedom Ferry dock at Straight Wharf, buzzing with the local shops and restaurants that make Nantucket so alluring. Upon exiting the ferry in the warmer months, The Gazebo serves up cocktails, including the ever-popular mudslide, to throngs of revelers enjoying the outdoor setting. Strolling along the waterfront will bring you to an enclave of sea shanties that house small boutiques like The Skinny Dip. This neighborhood welcomes treasure hunters searching for the perfect memento of their island sojourn. 

Heading up to Main Street on the cobblestone streets summons an awareness of the union of past and present. With each step on these stones, visitors breathe in salt air and adventure, hearkening back to centuries when whalers led horse-drawn wagons on this same thoroughfare. From a whaling community turned tourist getaway to an artist colony transformed into a luxury destination, Nantucket has a rich story to tell. 

Ten investors joined forces to purchase the island in the 1640s, inviting various tradesmen to join and call Nantucket home. Many of these family names are still prominent today, like Macy, Coffin, Starbuck, and Folger. The name Nantucket was dubbed years later, believed to mean “faraway island” in Wampanoag. 

The spirit of this land and its inhabitants has been molded by distinct periods, first thriving in the 1820s as the busiest whaling port in the world. That perilous industry brought wealth to the island, visible today in the distinguished captains’ mansions on Main Street. Later, the decline of whaling brought a new industry to town, tourism. Charming summer cottages and hotels immediately prompted actors and other creative types to take the leap for an island vacation. 

The 1920s marked the roaring years of Nantucket as an art colony, transitioning from a fishermen’s island to a creative getaway. Whaling shacks repurposed into work spaces for incoming artists brought an imaginative flair to the island. In recent years, Nantucket has become a luxury destination for thousands of visitors annually. 

Today, the island’s business owners exhibit the same initiative brought to Nantucket by its first settlers. Steps away from the ferries at Straight Wharf, Aunt Leah’s Fudge is tucked away off the street, emitting a decadent aroma of Nantucket chocolate covered cranberries and fudge. With over thirty flavors, this fudge is the perfect treat for yourself, or even to order as a favor for a special event.

Continuing onward brings you to Main Street, a historical haven and home to some of the island’s most beloved boutiques. The street would not be complete without The Club Car, a restaurant featuring fresh, locally-sourced meals, located at 1 Main Street. The bar may be the most exceptional place to enjoy a drink: inside an antique railcar. Owner Tanya McDonough and chef Mayumi Hattori create a dazzling ambiance with innovative tapas and seafood plates, so be sure to wander in before your downtown journey ends. 

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In the midst of the street’s action, Erica Wilson has been home to handstitched needlepoint designs and Nantucket style clothing since 1957. Island scenes are crafted in needlepoint on pillows, key fobs, belts, and more. The shop also features Heidi Weddendorf’s famed jewelry. Weddendorf’s pieces illuminate Nantucket life in her pearl designs, as well as the Nantucket Knot in gold or silver, bound by a leather bracelet band. Stop by the store for these designers’ timeless Nantucket collectibles, open year-round. 

Further up the street, get lost in the aisles of Mitchell’s Book Corner. Its sister store, Nantucket Bookworks, is located just a few blocks over on Broad Street. Each is its own little getaway, stacked with a diverse array of stories and trinkets. Above Nantucket Bookworks hides a book lover’s dream: a three-bedroom apartment available for stay, lined with walls of bookshelves. Both shops are oases bursting with charm since the late 1960s.

Nestled at the top of the street stands Murray’s Toggery Shop, a Nantucket staple since 1945. Here, the iconic Nantucket Red pants were born, a recognizable symbol of New England’s coastal style. A shopping tour of Main Street should definitely include a trip to Murray’s, with the authentic Nantucket Reds serving as the perfect takeaway from your island getaway.

To discover more on the side streets, head down Federal Street and check out Eye of the Needle, home to eclectic, quality women’s clothing in a modern space. This trendy boutique will surely enhance your wardrobe with its distinctive pieces, like painted jean jackets, recycled designer bags, and funky jewelry. Pop inside this creative world and get to know owner Karen Gollov, her friendly staff, and signature pieces.

A stone pathway on this road opens up to the world of the Peter Beaton Hat Studio. Stacks of sun hats peak through the doorway, luring visitors into this earnest space. Owner Darcy Creech’s journey began when she made a hat to wear to a party in 1989. “I made a hat, people loved it, and I thought, maybe I can do this for a living,” Creech reflects. Her notoriety skyrocketed when Hillary Clinton commissioned a hat for the presidential inauguration in 1993. She leveraged the newfound notoriety and sold her company, moved to the island with her seven-year-old son, Peter Beaton Creech, and opened the shop in 1996. Pop by the store to experience this eclectic space—it will not disappoint.

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For artful jewelry from across the globe and exquisite paintings by local talent, visit The Vanderbilt Gallery farther down Federal Street. Stop in and say hello to owner Barbara Vanderbilt, who can point out distinctive pieces like necklaces crafted from piano wire. Vanderbilt came to the island in 1972 and never left, continuing to curate her highly unique business. 

Right up the road on Broad Street, the Whaling Museum is a must-see for an immersive understanding of the whaling industry, a crucial piece of the island’s famed history. Open daily through December 31, the museum showcases a sperm whale skeleton, the Hadwen and Barney candle exhibition, and an impressive scrimshaw collection. Carve out time in your island stay for a first-hand glance at this magnificent collection of the whaling industry.

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Next, heading down South Water Street will lead to up-and-coming ventures like PPX Events, an event planning and catering company that is showcasing its hospitality talent. Owners Courtney Mackey and Lindsay Daley curate custom events in this nautical, earthy space, with chef Kyle Daley preparing meals on-site. The team also caters off-site venues, transporting their flair to your chosen location. 

Next door, The Beet is making its mark on the Nantucket dining scene, whipping up elegant, healthy foods for breakfast and lunch. As a year-round spot, owner Amy Young and chef Felino Samson have a newly released fall dinner menu with a Filipino twist. “This is truly unique and authentic. We wanted to offer something to the community that is a good value, and hopefully become a pillar of the year-round community,” Young comments. 

Around the corner is The Nautilus, an innovative eatery with an Asian-inspired take on the island’s seafood classics. Take a shopping break for a fresh meal in a modern, coastal environment. To pair with your meal, the cocktail menu offers inventive concoctions like “My Mom’s Maple,” with bourbon, maple syrup, and lemon.

Wandering down Easy Street will unveil a serene water view and the striking world of Susan Lister Locke. On display in her gallery are her high-end jewelry pieces. Among these gems are fine jewelry items, like gemstone rings, as well as her Nantucket Collection of unique island designs. Taking home one of these pieces will be something to treasure for a lifetime, forever harboring your island memories.

Searching for a boost of energy along your tour? Head over to the Handlebar Café on Washington Street and ask for a cup of sunshine. The café crafted this distinctive drink, complete with orange and yellow hues, as a year-round pick-me-up. “In the middle of winter, a cup of sunshine is perfect. It was our way to combat living on the island 30 miles out to sea in the cold winter,” owner Jason Bridges laughs. The Handlebar opened six years ago, when Jason and his wife, Courtney, stumbled upon this space right by their other popular business, Nantucket Bike Tours. Stop by the café for social atmosphere and a dose of sunshine.

These business owners carry their gusto right into the holiday season. Come the first weekend in December, the annual Nantucket Christmas Stroll brings tourists and shoppers alike to enjoy small-town holiday cheer. Mark your calendars—the 2019 Stroll is scheduled for December 6-8th. On Friday, the Whaling Museum becomes a wonderland for the Festival of Trees, a month-long exhibition with trees designed by local groups. Saturday, head to Main Street for carolers, live music, crafts, and restaurant and shop specials. Topping off the excitement, the Town Crier leads the crowd to meet Santa at the wharf. This is the most joyful time to visit your favorite spots, like the island’s own brewery, Cisco Brewers. 

An adventure to Cisco Brewers at any point in your visit will always quench your thirst and feed your spirit. A quick drive from town, Cisco is open daily, with a downtown shuttle service providing transportation for its growing following. The expansive property has four working companies: a winery, distillery, brewery, and farm. In the 1980s, Nantucket Vineyards began, with Cisco Brewers and Triple Eight Distillery following some years later. Today, Cisco Brewers is an outdoor haven to enjoy a beer, some wine, or a cocktail. For a light bite, food trucks are often stationed outside, offering an array of tasty treats to accompany your drink.

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If you wish to extend your island time, there are countless inns around the downtown area. The Union Street Inn offers bespoke seamlessly styled rooms for a cozy stay. The inn is complete with a private outdoor area and gourmet breakfast, so stroll along the cobblestone streets and find your temporary home here.

For a luxurious resort experience, The Nantucket Hotel has mastered amenity and ease for their guests. Equipped with beach shuttles, pools, a spa and an exercise facility, as well as multiple restaurants, this is a gorgeous spot for a luxury Nantucket vacation. Enjoy this top-notch service in the fall and winter months, warming up by the fire pits after a quiet day. 

Wrapping up a full day on the island, unwind with a dining experience at Cru. Open since 2012, Cru has become a headliner in the island’s restaurant scene, where every table relishes the harbor view. Chef Erin Zircher updates New England classics with her own style. “We are not reinventing anything, rather, adding our spin, making it fresh and vibrant,” Zircher notes. Her diverse training in Vermont, Chicago, Boston, and France remains with Zircher, who describes her own style as harnessing “Mediterranean sensibilities with French technique.” As for your experience at Cru, Zircher recommends beginning with oysters, moving on to local seafood like the warm buttered lobster roll, and finishing by indulging in her favorite dessert: the homemade whoopie pie with vanilla bean buttercream and sea salt. The restaurant, like many local establishments, closes after Columbus Day, but reopens for Christmas Stroll weekend.

Before departing, soak in the view at Brant Point Lighthouse, one of three lighthouses on the island and a quintessential spot to enjoy the golden hour. Originally built in the mid-1700s as a guide for whalers returning home, Brant Point is now a picturesque scene on the harbor, still serving as the port’s landmark. 

A trip to this unique island will undoubtedly result in a special memory, but since it will always be unforgettable, you may want to begin planning your return as soon as you cast off the dock. 

For more Nantucket fun, check out our 2019 Best of Guide!