Take in the island’s famous sunsets on the water during a two-hour sail aboard the Classic Harbor Line’s new Schooner America 2.0 (November to April, $75 per person), a 105-foot sailboat modeled after the 1851 winner of the America’s Cup, which made its first trip in November. Grab a seat by the captain and ask about the treasure recently found off Key West as you sail out to Sand Key reef.
Skip the active but underwhelming art scene and instead head to the Key West Museum of Art & History ($7), currently hosting an exhibit celebrating the centennial of the 100-plus-mile Oversea Railway, which linked Key West to the Florida mainland for the first time. Other exhibits focus on the Spanish-American War, former resident Ernest Hemingway, and life on the island in the early twentieth century as depicted in a series of wooden reliefs.
Traverse the two-by-four-mile island by bike, especially if you’re staying in the historic Old Town, where it’s next to impossible to park a car. Eaton Bikes ($18 a day) delivers beach cruisers to hotels and offers roadside assistance if you have any troubles. Be sure to ride to the island’s best beach at Fort Zachary Taylor Historic State Park.