On our second day, we went to a wine tasting on this street in front of the Pitti Palace, at Gola Pitti e Cantina.
Our sommelier, and one of the enoteca owners, was Zeno. He is passionate about wine! I had read online a complaint about this place...some Americans had gone in there and only wanted food, no wine. Said they don't drink wine. They got kicked out and told not to go to a wine bar if they don't like wine! Zeno said he's the one who kicked them out.
Luckily, we do like wine. And Zeno knows his stuff. The shop carries only Tuscan wines, and only ones the owners drink themselves. I think our wine tasting was $30USD each, and it lasted 4.5 hrs and included 12 wines and cheese. We had a great time. Zeno showed us on a map where the wines came from, and showed a slide show of the vintners.
Our tasting was down in one of the cellars and a nice couple from San Diego was there too. We met a LOT of Californians in Florence.
We went back another day just to have a glass of wine. On that day, a couple came in and wanted wine in plastic glasses to drink in the square across the street. One of the other owners just looked at them dead-pan and said, "We don't serve wine over there." After they left, Zeno told us that wine in a plastic glass is a big offense.
So just don't do it! And NEVER mention box wine! I shudder. One of the wines we tried was hand numbered by the vintner. We had a great time at the wine tasting. All the wines were delicious and Zeno was informative and friendly. I would recommend it to anyone. But...respect the wine! Or else. :)