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The best way to experience the culture of any country, is immersing in their small villages where time seems not keeping pace with the chaotic cities. The magic of Tuscany is exactly this, contemplate the grandeur of yesteryear in their small villages protected by medieval ramparts. Watch the unique landscape that runs olive trees, vineyards, cypress trees and forest strata, enter their "trattorie" to enjoy typical specialties of the area in their wine cellars and taste the best Italian wines.
Ditto for Emelia-Romagna. The tiny towns (albeit with their challenging tiny roads, and curious signage) will bring you to another experience, more restful than the major cities. There you can find wonderful Parmigiano-Reggiano, Lambrusco, Balsamic Vinegar and numerous hand rolled pastas in any local place -- for completely reasonable prices (complete meals 20-35 Euros per person with many courses, wine, coffee, water, dessert included)
English is not spoken by everyone, but you will likely find SOMEONE willing to play charades, or fill in the blanks with a phrasebook - and have no issues. Younger people especially are quite fluent. Off the beaten path, it was so wonderful to feel the genuine welcome to their region.