Many visitors to Nantucket feel that when they step off the ferry, they are taking a step back into history. And with good reason! The cobblestones lining the roads downtown were brought here in ships; the island—affectionately known as The Gray Lady—is dotted with historic sights such as the Old Mill and the Nantucket Atheneum; and most island homes feature grays and white, the colors of tradition and calm. To cement the image, the entire island was named a National Historic Landmark in 1975.

Learn more about the island’s history at the Nantucket Whaling Museum, or pay a visit to the island’s three historic—and very attractive—lighthouses. The Nantucket Shipwreck & Lifesaving Museum also offers information on the more than 700 ships that have wrecked over the years in Nantucket waters.

Another historic spot, Main Street Square, bustles with art galleries, gift shops and great restaurants. Stop in one of several lightship basket merchants to browse one of the island’s famous creations. Get a feel for how the locals live by slipping on a pair of Nantucket reds; Murray’s Toggery Shop offers a colorful selection. Nearby, the Dreamland Theater on South Water Street offers a lively schedule of films, opera simulcasts and other unique events.

A great way to explore different parts of the island—from Madaket to Siasconset—is by bike, as Nantucket has more than 30 miles of bike paths and several great rental shops. The island’s narrow roads and massive homes are beautiful, and there are flowers and quirky quarterboard signs everywhere.

En route, stop for a sandwich or snack at Bartlett’s Farm, or enjoy a sweet ice cream at the Juice Bar on Broad Street. Another great spot for a bite is Barcos y Tacos, which offers tasty breakfast tacos and burrito bowls on Sanford Road.

Staying here? For a one-of-a-kind experience reserve a room at the luxurious White Elephant, a hotel famous for its airy suites and wonderful views of the harbor.

Not to be missed, Nantucket has a boatload of beaches, including Jetties and Surfside. For refreshment of a different sort, Cisco Brewers is the perfect spot to take in some great live music, fresh island air and a locally brewed beer!