Hotel: Chelsea Hotel

The Chelsea Hotel is nothing short of legendary. Sure, it may be in need of a renovation and good scrub, but that's part of its charm. This 12-story New York City landmark (it was the tallest building in the city until 1899) has been located in the heart of the Chelsea neighborhood since the 1880s, when it was surrounded by farmland. You can't miss its red façade with ironwork balconies, and its funky lobby is full of huge, original, and ecletic artwork. But most of all, it's known for its long list of famous creative types who have stayed or lived here, including Mark Twain, Thomas Wolfe, Allen Ginsberg, Eugene O'Neil, Arthur Miller, and William Burroughs, and rock stars like Sid Vicious, Janis Joplin, Bob Dylan, and Jimi Hendrix. The rooms are large by NYC standards and some have private kitchens and bathrooms. About half the 300 or so rooms are occupied by year-round tenants, and the remaining 50 percent are available to overnight guests. Even if you do not stay at the Chelsea, a visit to its lobby should be on your New York itinerary.