GetYourGuide's Florence day trips repeatedly feature Siena, San Gimignano, Chianti and Pisa. They fit a road trip — just not one rushed day.
Florence as a base
Give Florence two full days first. The historic centre itself is better explored without a car.
Siena, San Gimignano and Chianti
These stops fit geographically but a DIY trip needs buffer time. If driving, plan wine experiences responsibly.
Pisa and Lucca
Pisa makes a natural stop and Lucca adds a calmer contrast. Verify access restrictions and parking from official sources.