Chelsea Hotel, W. 23rd Street

Steeped in a rich Bohemian history, the vaunted Chelsea Hotel (222 W. 23rd St., 212-243-3700) has been a fixture in this neighborhood since it opened (it was actually built as an apartment building in the 1880s and was NYC's tallest building until the end of the 19th century). Many famous guests have lived here, including queer beat poet Allen Ginsberg, and such diverse figures as Sid Vicious (of the Sex Pistols), who stabbed his girlfriend here to death, and poet Dylan Thomas, who died here from excessive drinking. William Burroughs, Jasper Johns, Patti Smith, Bob Dylan, and many others have stayed here. Despite its being a Chelsea icon, the hotel doesn't have a tremendously gay following - it's more just a favorite address of artists and creative sorts. Rooms have a happily dated vibe and are rather unfancy but rich with character, and you can't beat the location - close to gay Chelsea nightlife and dining (and it's nearly across the street from David Barton Gym). It's also a great NYC bargain, with rates typically running well under $200 per night - the cheapest rooms have shared bathrooms. Pricier ones have kitchenettes. Another affordable, gay-friendly hotel is just down the block, the Chelsea Savoy Hotel. In the other direction, you'll find such gay-friendly restaurants as East of Eighth and F & B Gudtfood.