Massandra, 1775: $43,500
Russia’s legendary Massandra winery produced a legendary sherry in 1775, which was sold at a Sotheby’s auction in London in 2001. It’s the most expensive sherry ever sold, coming in at $43,500 for the bottle. After serving a few of their rarest wines to Russian President Vladimir Putin and Italian media mogul Silvio Berlusconi, the winery has been in some trouble, since their wines aren’t supposed to be sold or given away without presidential permission.
