Do I need to speak Italian to find authentic experiences?

Not fluently, but learning 20 phrases like 'Vorrei' (I would like) and 'Per favore' goes a long way in showing respect to locals who aren't used to speaking English.

Is it rude to walk into small village shops?

Not at all. Just offer a cheerful 'Buongiorno' when you enter and 'Grazie, buona giornata' when you leave.

Finding authentic local experiences in Tuscany

Ditch the main piazzas of Florence and Siena; instead, base yourself in a village of fewer than 2,000 residents and prioritize visiting agriturismi that focus on production rather than just hospitality. Seek out sagre (local food festivals) and village markets to interact with residents on their own terms.

Pick a secondary base. Avoid staying in tourist-saturated cities. Choose a base like Pienza, Anghiari, or Pitigliano. You’ll be surrounded by locals doing their daily shopping rather than tour groups.
Use the 'Sagra' calendar. Look for posters on telephone poles or check 'Sagra Toscana' websites. These are town-specific food festivals celebrating one ingredient (like wild boar or truffles). They are 100% volunteer-run by the local community.
Visit 'Producer' Agriturismi. Don't just stay at a farm for the view. Call ahead and ask if they produce their own olive oil or wine and if you can observe or assist in the harvest or pressing process. Authentic farms will be happy to show you their work.
Shop at the weekly market. Every town has a market day. Go at 8:00 AM. Bring cash. Buy your pecorino cheese and seasonal fruit from the same vendors the local nonnas are using.

Do I need to speak Italian to find authentic experiences?: Not fluently, but learning 20 phrases like 'Vorrei' (I would like) and 'Per favore' goes a long way in showing respect to locals who aren't used to speaking English.
Is it rude to walk into small village shops?: Not at all. Just offer a cheerful 'Buongiorno' when you enter and 'Grazie, buona giornata' when you leave.