City Cheat Sheet: A Travel Guide for Nantucket, Massachusetts

Far off the coast of Cape Cod sits the quaint island of Nantucket, home to reclusive celebrities, a thriving sailing culture, a storied whaling history, a respected culinary scene, and more than 80 miles of coastline—all of which make it an ideal summer destination. With the season in full swing, we asked The Scout Guide Nantucket editor Stacey Leuliette to fill us in on how to enjoy a quintessential Nantucket weekend, from visits to local institutions to sunset vistas to all the raw oysters you can handle this summer—and all year round.

Go Where the Locals Go

“I always like to take my visitors who come to Nantucket for the first time to CRU,” Stacey says of the oyster bar located at One Straight Wharf, 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.”

Within the same vicinity as CRU, you can experience the oceanside vibes at local favorites including The Gazebo at The Tavern Nantucket Island (4 Harbor Square) and Straight Wharf (6 Harbor Square). Right outside of town is another special Nantucket institution, Cisco Brewers (5 Bartlett Farm Road), where locals love to gather during the day to listen to live music and sample food truck fare and beer flights.

After the sun goes down, Stacey recommends paying a visit to the legendary Nantucket spot The Chicken Box (16 Daves Street), which has live music every night during the summer. “On Nantucket, we say ‘let’s go to the Box,’” she says, likening it to a beloved college bar with fantastic bands where everyone of every age dances.

In the morning, locals gather at the cozy Black Eyed Susan’s (10 India Street) for locally revered coffee and an eclectic menu. While you should be prepared to wait for a table for breakfast, the lines are somewhat shorter in the evenings, when the restaurant, which has a BYOB policy, serves dinner.

Enjoy the Outdoors Like an Insider

Sailing is the primary pastime in Nantucket. If you’re interested in learning the local way of life but don’t have access to your own vessel, Stacey recommends sailing lessons and rentals through the team at Next Level Water Sports, or Island Boat rental, where you can rent a boat for the day, with or without a license. For families, she suggests Critter Cruise Nantucket, during which Captain Josh will pull up critters from the sea aboard the Monomoy, allowing the kids to experience sea life firsthand. Meanwhile, those seeking high-end charters and fly and spin fishing should try Bill Fisher Outfitters.

For a beachfront run, bike ride, or rollerblade excursion (Stacey’s favorite), hit Madaket Beach, which boasts a six-mile-long path out to the ocean. Another ideal place for a waterfront walk is The Moors, which is made up of more than 3,000 acres of open, conserved space on the island, with miles and miles of walking trails, and, according to Stacey, feels a bit like you’re at the end of the world. When embarking on a stroll through The Moors, she 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, and adds, “Don’t forget to grab the Nantucket Conversation Foundation’s Middle Moors map!”

Nicknamed the Grey Lady because it’s often shrouded in fog, Nantucket is anything but colorless at the end of the day. “I always take people to Galley Beach (54 Jefferson Avenue) to watch the sunset,” says Stacey. “It’s the best place on the island to see it, with a great restaurant of the same name. It has the best views on Nantucket.”

Eat Where the Foodies Eat

Nantucket is that coveted combination of a beachfront town with serious culinary cred. You can’t go wrong at any of the Nantucket institutions Stacey recommends above, but epicureans might also want to try some of the lesser-known restaurants while on the island.

Like any true Nantucket local, Stacey is partial to oysters. At The Nautilus (12 Cambridge Street), the menu plays on haute Asian street food, and the tempura east coast oyster tacos are a decidedly delicious way to enjoy the local delicacy. Ventuno (21 Federal Street) is a local foodie attraction, with small plates worth ordering more of; Stacey recommends their soft-shell crab when you can get it. Meanwhile, Lola41 (15 South Beach Street) is her pick for sushi featuring Nantucket-fresh catches and a side of the famous truffle fries. Last but not least, health conscious foodies flock to Lemon Press (41 Main Street) for breakfast and lunch for down-to-earth farm-to-table fare and, of course, juice.

Shop with the Locals

If you’re looking to do a little browsing, you can spend an entire afternoon walking up and down Main Street or Center Street hitting a wide range of stores. As a designer herself, Stacey is always looking for beautiful home furnishings, and 28 Centrepoint is among her favorite stops for Nantucket-chic home accessories. Nantucket Looms (51 Main Street), which makes all of their own products and has wonderful handmade blankets and linens, is another frequent destination.

Skinny Dip (23 Old South Wharf Road), a design collective right on the wharf, is the perfect place to shop for stylish boating attire. Another must-visit local favorite is Current Vintage (4 Easy Street), which offers a curated selection of vintage pieces—plus wine and cheese.

For gifts, Stacey frequents ACK4170 (1A Old North Wharf). The name mixes Nantucket’s airport code with its map coordinates, and there is no better place to find locally made goods, including a number of perfect hostess gifts. Last but not least, don’t miss the opportunity to stop inside Coe + Co Gallery (38 Centre Street), which features world-class photography exhibitions all season long.

Where to Stay

White Elephant (50 Easton Street) is a luxurious resort right on the harbor that has landmark status—plus many options for water sports, a phenomenal spa, and a central location that makes everything walkable. For families, Stacey recommends Harborview Cottages (24 Washington Street), where guests can have their own place to relax, with all the amenities of a hotel. For design-focused travelers, there is Greydon House (17 Broad Street), which Stacey describes as having the perfect quintessential Nantucket vibe with incredible style, in addition to a buzzy restaurant.

When to Go

If you can’t make it to Nantucket for the season, Stacey believes that Christmas may be an even better time to visit the island. Though she lives in Palm Beach for the winter, she prefers Nantucket at Christmastime, particularly the first week of December when the entire island is strung up with lights for the Christmas Stroll and everyone gets dressed in their festive best. “It’s a little jolt of Christmas right after Thanksgiving, and there is no better place to be to start that season,” she says.

Photography by Rebecca Love Photography. For additional recommendations for what to do, see, and experience in Nantucket, Massachusetts, follow The Scout Guide Nantucket on Instagram.