Madonna 's first musical recordings and the instruments on which she learned to play are up for auction. The sale will also feature a treasure trove of artefacts from New York's cool pop culture history. The Guernsey's auction house event celebrates 60 years of downtown Manhattan's history and culture with personal items from the Holiday singer, as well as a historic Bob Dylan master tape recording.

Also included in the sale will be offerings from the fabled Chelsea Hotel, including Janice Joplin's door, many of the beautiful stained-glass windows, and the iconic over-sized neon double faced sign on the top of the hotel. Highlights of the auction are Madonna's earliest guitar and drums, handwritten letters, and audio tapes of her first band recordings. A young Madonna, before embarking on a successful solo career, teamed up and formed the New Wave punk band "Breakfast Club" with brothers Dan and Ed Gilroy circa 1979.

Guernsey's say: "Back in the 1970's, the aspiring singer and dancer lived with her then boyfriend Dan Gilroy and his brother Ed in a former synagogue in Queens, NY, which still stands. "There the fellows taught the ambitious blond how to play on the guitar and drums included in the auction and she began writing and singing her own material." Another high profile lot is Bob Dylan's original recording session master tapes for his first album, "Bob Dylan" (Estimate $300,000 - $500,000).

In addition, there are items from The Chelsea Hotel, which was an incubator of c.