First Italy trip, Tuscany + Florence tips?

Going to Italy for the first time with a group. Staying in Tuscany and doing Florence and Siena as trips.

Plan is pretty simple:

• wineries in Chianti
• Florence day trip (Accademia, food, walking around)
• Siena evening
• one free day

Looking for:

• good food spots in Florence that aren’t traps
• whether Siena needs a plan or just explore
• how tough the walking is
• reservations vs winging it
• cash vs card
• any etiquette stuff people mess up

Also, if any women here have tips on staying safe or things to watch out for, I’d really appreciate it.

Thanks