The second largest of 13 main islands of Massachusetts is just 30 miles off Cape Cod's coast. At less than 48 square miles, Nantucket is home to authors and celebrities, cobblestone streets, and iconic architecture. Although it's open to visitors year-round, the island undoubtedly comes alive in the summer. With its hydrangeas and salty air, you're sure to be entranced by the island known as "The Grey Lady."
Nantucket features some breathtaking beaches, each with its own personality. Families staying closer to Nantucket Town should consider Jetties Beach. If venturing away from town, head to Madaket Beach for surf and stop by Millie's on your way out for a Madaket Mystery, a boozy local cocktail. Although a car or taxi ride is required to travel to most island beaches, Nantucket offers public transportation via its bus system, The Wave. Restrooms and changing facilities may be limited, so plan accordingly.
While the lighthouses themselves aren't open to visitors, Nantucket's three lighthouses provide stunning vistas and Instagrammable backdrops. Go to Brant Point Lighthouse for the shortest distance from town to enjoy harbor views. For an interesting landscape and a neighboring golf course, head to Sankaty Head Lighthouse. Those craving an off-road adventure can visit Great Point Lighthouse, set on the Coskata-Coatue Wildlife Refuge. A four-wheel-drive vehicle and an updated beach permit are required for access.
You won't want to miss local eats while on the island. Downyflake, Black Eyed Susans, and Island Kitchen are favorites for breakfast and brunch. You'll definitely want to grab a sandwich (and carrot cake or a cookie) from Something Natural. Nantucket also has its share of fine dining options. The culinary expertise of Michelin-starred chef Joseph Keller at Company of the Cauldron is an experience you won't soon forget. You might also want to book a table at The Chanticleer for a romantic dinner. Just be sure to leave room for ice cream at The Juice Bar.
Nantucket offers over 35 miles of trails for those wishing to explore the island. Bike shops are conveniently located in town, with Nantucket Bike Shop and Young's Bicycle Shop on Broad Street. Nantucket Bike Shop offers guests the choice of bike or scooter rentals, while Young's offers bicycle and even car rentals to those eager to venture out of town. If you're staying in Mid-Island, Island Bike Company and Easy Riders Bicycle Rentals provide additional options for cyclers.
Established in 1995, this local haunt is named after the eponymous beach and section of Nantucket. Park here for the day and sample some of Cisco's brews or wine and spirits from Nantucket Vineyards or Triple Eight Distillery. Bands provide the perfect soundtrack, while food trucks serve up local fare. If you're craving a Cisco experience off-island, you can visit one of their four other New England locations. Just be sure to check the hours of operation, as some locations are seasonal.
For a rainy day or night out, the Nantucket Dreamland Theater ("the Dreamland" among locals) offers the perfect indoor activity. With showings year-round and a seasonal drive-in, you won't miss your favorite blockbuster hit. The Dreamland also hosts cultural workshops and live performances, so be sure to check out their event schedule during your visit.
Shop like the locals and visit Murray's Toggery, Erica Wilson, or Skinny Dip while in town. Fashionistas can find pop-ups for brands like Veronica Beard or resort wear maven Lilly Pulitzer's at their Nantucket outpost. Nantucket Book Works and Mitchell's Book Corner have you covered with your next beach read, while Annie & the Tees and the Sunken Ship have your souvenirs and Nantucket merch.
Siasconset, or Sconset, a quaint village about eight miles from Nantucket Town, is perched where the Atlantic Ocean meets the east end of the island. Stop in Sconset Market for a brownie or spend the day at Sconset Beach. Hit up the piano bar at The Summer House or go to The Chanticleer for a candlelit dinner. You can also catch a flick at the old Sconset Casino.
During the late 18th and early 19th centuries, Nantucket was the whaling capital of the world. Nantucket even appears in Herman Melville's Moby Dick and is described as "away offshore." Tour this museum for a journey into Nantucket's history in the whaling industry. Don't miss the 46-foot sperm whale skeleton as well as the sweet rooftop deck with harbor views.
For the full island experience, consider a fishing excursion. Tour operators on the Straight Wharf offer charter options for visitors and islanders alike. Catch bluefish or striped bass while aboard vessels like the Just Do It Too, and leave with memories and dinner. If you're getting motion sickness just reading this but savor the idea of a fresh fish dinner, you can barter for that day's catch when the boats come in.
Located in Sconset, the bluff walk offers visitors a Secret Garden-esque experience. This public walkway runs through the backyards of iconic Nantucket cedar shingle homes along the Atlantic coast. Hikers trek through gardens and lattice archways while taking in staggering views of the beach on one side and impressive homes on the other.
Consider a walking tour if you're eager for more Nantucket history. These 60-minute tours range in topic from notable writers of Nantucket to ghost tours at night. Organized and operated by the Nantucket Historical Association, the excursions offer visitors a different, deeper perspective from the usual tourist impression, and you may leave with some additional knowledge of this mystical island.
While a trip to the public library might not be on everyone's vacation must-do list, the Nantucket Atheneum is not your typical public library. The Atheneum boasts a grand exterior with stately brick and wide columns. Comb through their extensive catalog or participate in a program or event. You might even catch an interview with a notable author during your trip!
Built as a wedding gift for Jethro and Mary Gardner Coffin, the Oldest House is the sole structure of its kind that has survived since the 17th century. Tours of the Oldest House are free to visitors and provide a peek into the lifestyle of an entirely different era. Guests can tour all the rooms in the house, including the great hall, parlor, kitchen, the "borning room," and the second-floor bedrooms.
Nantucket is largely an island full of activities enjoyed during the day, while the town tends to get quiet at night. However, there are few places around town where you can dance the night away. One such place is The Chicken Box or The Box. Located in Mid-Island, the Chicken Box is Nantucket's answer to nightlife with billiards tables, bar games, and a stage for local talent in a cedar shingle house.