8 Days in Florence. Day trip suggestions?

We did 2 day trips with WalkAboutFlorence - the BEST OF TUSCANY TOUR (incl. Siena, Pisa, San Gimignano) the CHIANTI WINE & FOOD SAFARI TOUR.

You can read reviews & see photos on TripAdvisor, but book direct on the WalkAboutFlorence website.
Both tours were excellent.

Put Siena high on your list. Also San Gimignano, Pisa, Cortona, Montepulciano and Montalcino. You can see several of these places on one day trip.

I'd go to Bologna--less than 45 minutes train ride.
Florence to San Marino is about 3 hours each way.

I would take the bus to Siena so you can spend more time there than you would on the tours that go to other places on the same day.

I really enjoyed my day trip to Lucca when I was in Florence a few years ago. It’s a nice change from the crowds. I mainly walked around, window shopped, ate gelato, had lunch, and visited some churches.

Siena, San Gimignano and Pisa in that order.