City Cheat Sheet: A Travel Guide for Nantucket, Massachusetts

Nantucket harbor. Photography by Rebecca Love Photography.

WHY SHOULD ONE VISIT THE IDYLLIC ISLAND PARADISE of Nantucket, Massachusetts? The Scout Guide Nantucket editor Stacey Leuliette can name a few reasons. First up, this bucolic beach town offers a unique community feel. “The island is home to so many creative, unique individuals year-round, and is a gathering place for even more during high season,” Stacey says. And even though summer is the peak time to visit, when the town and island are all abuzz with visitors and a busy social calendar, Nantucket offers something enchanting year-round. Last but not least, Nantucket provides endless ways to enjoy the outdoors, from the pristine beaches and exceptional sailing to countless bike paths around the island beckoning locals and visitors alike to enjoy and explore. “Nantucket is home to 82 miles of pristine coastline, a true postcard come to life,” Stacey says. 

Ready to plan your next getaway to Nantucket? Read on for Stacey’s  favorite local finds and activities for taking in her city.

*Please note that due to COVID-19 some of these businesses might be closed or have specific guidelines in place. We recommend calling ahead and/or visiting their websites for the latest information on their status, offerings, etc. 

THINGS TO KNOW // Located 30 miles out to sea from the mainland and accessible only by ferry or flight, the 14-mile-long and 3.5-mile-wide island of Nantucket is the epitome of summer New England life. There, you’ll find gentlemen in preppy attire, and most of the island’s homes are adorned with gray, natural wood shutters. Speaking of the structures, the island boasts the highest concentration of pre-Civil War homes in the U.S., plus many historic sites. 

WHEN TO GO // From the charming inns and boutique hotels to the award-winning restaurants and cobblestone streets, the town comes alive in the summer months. If you can’t make it to Nantucket for the season (or prefer to avoid the crowds), Stacey recommends visiting the island in the fall. And although she lives in Palm Beach during the winter, she prefers to kick off the holiday season at Nantucket Stroll. “During the first week of December, the entire island is strung up with lights for the Christmas Stroll and everyone gets dressed in their festive best,” she says. “It’s a little jolt of Christmas right after Thanksgiving, and there is no better place to be to start that season.” 

WHERE TO STAY // White Elephant (50 Easton Street). This luxurious resort right on the harbor has landmark status—plus many options for water sports, a phenomenal spa, and a central location that makes everything walkable.

Harborview Cottages (24 Washington Street). When you’re visiting with family in tow, Stacey recommends these cottages, which allows guests to have their own place to relax while enjoying all the amenities of a hotel. 

Hotel Pippa (17 Broad Street). For design-focused travelers, Stacy recommends this hotel, which has the perfect quintessential Nantucket vibe with incredible style, in addition to a busy restaurant. 

WHAT TO DO // Nantucket Whaling Museum (13 Broad Street). Managed by The Nantucket Historical Association, which was founded in 1854 and also manages eight additional historic sites around the island, including Hadwen House and Greater Light. The Whaling Museum is a must-visit with 9 galleries and more than 1,000 artifacts and works of art. 

Explore the island by bike. One of the most popular pastimes in Nantucket is to tour the town by bike via one of the many trails. You’ll find a trail to the Brant Point Lighthouse, and also trails in Madaket, Surfside, and Sconset.

Dreamland Film & Cultural Center (17 S Water Street). This small, historic theater houses a cinema and hosts many performing arts events and community activities.

Bill Fisher Outfitters (20 N. Cambridge Street). For those seeking high-end charters and a fly and spin fishing lesson, this is the place to go. 

The Moors (306 Polpis Road). Made up of more than 3,000 acres of open, conserved space on the island, walking here feels a bit like you’re at the end of the world. Stacey says it’s best to go to the Windswept Cranberry Bog parking area and head off to the right, down through the tree-lined path leading to the bogs. She also recommends grabbing a Nantucket Conservation Foundation’s Middle Moors map.

Steps Beach and Galley Beach (54 Jefferson Ave). Nicknamed the Grey Lady because it’s often shrouded in fog, Nantucket is anything but colorless at the end of the day. Stacey always takes people to Galley Beach to watch the sunset and notes that the restaurant is worth a visit. 

Sankaty Head Light (122 Baxter Road). A beloved Nantucket icon, Sankaty Head Lighthouse has been active to aid navigation for more than 160 years and is visible 25 miles at sea. 

Nantucket Atheneum (1 India Street). A private and non-profit organization that prides itself on honoring the island’s history, the Atheneum provides public library service to the island’s year-round and seasonal residents. 

WHERE TO SHOP // Current Vintage (4 East Street). A must-visit local favorite offering a curated selection of vintage pieces—plus wine and cheese. Owner Beth English has an incredible eye for the best fashion finds and a beautiful selection of wines and related items. 

Susan Lister Locke (28 Easy Street). Voted best jeweler on Nantucket, owner Susan’s love of drawing and fashion design generated a lifelong passion for art and its presence in all facets of her life. Always drawn to the beauty of sea and nature, Susan’s work incorporates patterns and design found in nature in 18 karat gold and other metals with vibrant gemstones. 

Jewel in the Sea (6 Straight Wharf). Owned by sisters Kate and Meghan Trainor and Meghan’s husband Jack, this darling shop on the wharf features classic Nantucket-style jewelry and custom engagement rings. Jewel in the Sea proudly makes all of their products in house, hand-signing each piece. Every piece is one-of-a-kind, and weaves in the rich culture, history, and subtle style that defines Nantucket. 

28 Centre Point (28 Centre Street). As a designer herself, Stacey is always looking for beautiful home furnishings, and 28 Centre Point is among her favorite stops for Nantucket-chic home accessories. 

Erica Wilson (25 Main Street). Offering an eclectic mix of curated finds, this is one of Stacey’s favorites to shop on the island. In addition to women’s clothing, the shop also offers a large selection of needlepoint and children’s clothing. 

Murray’s Toggery Shop (62 Main Street). A retail legend on Nantucket, Murray’s is originally known as the island’s main supplier of essentials. Over the years, it has grown to become known as Nantucket’s department store with everything you need to dress on the island. Be sure to stop in and get a pair of iconic Nantucket Reds and check out their collaborations with Smathers & Branson, Tretorn, and others. 

Trinity Collection (50 Main Street). A special boutique featuring a collection of rare and vintage watches from the 1920s to 1960s, including Rolex, Omega, Hamilton, Longines, and Patek Philippe. 

Nantucket Looms (51 Main Street). This artisan shop embraces Nantucket cottage-style living and makes all of their own products. Don’t miss the wonderful handmade blankets and linens.

Skinny Dip (23 Old S. Wharf Road). Be sure to visit this design collective right on the wharf. It’s the perfect place to shop for the latest fashions. 

Samuel Owen Gallery (40 Centre Street). With locations in Greenwich, Nantucket, and Palm Beach, this gallery is always filled with incredible eye candy for the art connoisseur.

Coe + Co Gallery (38 Centre St). Last but not least, don’t miss the opportunity to stop inside this fine art photography gallery, which features world-class photography exhibitions by Nathan Coe and others all season long.

WHERE TO EAT // Lemon Press (4 Main Street). Featuring healthy organic juice and food, this is a delightful stop for breakfast or lunch.

Black-Eyed Susan’s (10 India Street). A local favorite for breakfast or dinner, be sure to go early as there is always a line out the door.

The Nautilus (12 Cambridge Street). Playing on haute Asian street food, the tempura East Coast oyster tacos are a decidedly delicious way to enjoy Stacey’s favorite local delicacy.  

Ventuno (12 Federal Street). With small plates worth ordering more of, this is a local foodie attraction. Stacey recommends their soft-shell crab, when you can get it. 

Proprietor’s (9 India Street). Named for Nantucket’s original landowners, Proprietor’s embraces Nantucket’s unique role as a whaling hub. This restaurant has internationally inspired flavors and family-style dining, plus great options for vegans.

Lola 41 (15 S Beach Street). For a nice night out head to this sushi restaurant for Nantucket-fresh catches and a side of the famous truffle fries.

CRU (1 Straight Wharf). Stacey always takes first-time visitors to CRU, an oyster bar located in the middle of a hub of outdoor Nantucket restaurants and bars. It’s a quintessential experience located right at the end of the dock, and it’s the perfect place to soak in the local scene.

The Gazebo at The Tavern Nantucket Island (4 Harbor Square). The Gazebo is a lively, open-side structure and the perfect spot for enjoying ocean breezes and Nantucket summer days or nights.

Straight Wharf (6 Harbor Square). Celebrating six decades on Nantucket’s harbor, this local favorite re-interprets summer classics.

Bartlett’s Farm (33 Bartlett Farm Road). an elevated farmers market with fine groceries, take-away, and a plentiful nursery that is a favorite for locals with herbs, flowers, and plants to take home.

The Juice Bar (12 Broad Street). If you’re an ice cream lover, be sure to check out the Juice Bar, but make sure to go early as lines often run out the door into the street!

Corner Table (22 Federal Street). Stacey’s favorite coffee shop in town for great tea, coffee, and gourmet grab and go items.

The Hub (31 Main Street). Nantucket’s version of the perfect magazine stand and coffee shop. You can also find Nantucket-themed take home items here.

Lemon Press (41 Main Street). This organic eatery and juice bar is Stacey’s favorite place to grab a fresh pressed juice. 

The Chicken Box (16 Dave Street). A Nantucket institution like no other. The Chicken Box is a bar featuring live music and an always unpretentious, friendly, and relaxing atmosphere. It will always be where people from all walks of life gather for fun and entertainment. 

Afterhouse (18 Broad Street). A wonderful seafood restaurant and wine bar with a focus on local ingredients, raw bar selections, and shared plates, with an extensive wine and beer list.

Club Car (1 Main Street). A wonderful spot for dinner, this local favorite also turns into a sing-along piano bar after hours.

Cisco Brewers (5 Bartlett Farm Road). Right outside of town is this special Nantucket institution, where locals love to gather during the day to listen to live music and sample food truck fare and beer flights.

LOCAL PRO TIP // The town is a collection of individually owned businesses—and events—that give the island uncompromising character and charm. From The Daffodil Festival (April) to the Figawi Regatta (May), The Nantucket Film Festival, Nantucket Book Festival (June), Cranberry Festival, Christmas Stroll (December), and countless other community occasions, Nantucket is one of the most festive and engaged communities. 

You can download this Nantucket cheat sheet by clicking here. For additional recommendations for what to do, see, and experience in Nantucket, follow The Scout Guide Nantucket on Instagram.