We are coming to Italy in April for a wedding. The first 2-3 days we will spend in Florence. Then we are at the wedding venue for a couple days outside of Siena. We have another 2 days to spend in Italy, but have not picked a destination yet. Not interested in Rome due to the crowds. We are more interested in authentic experiences and outside activities. 3 couples age range 25, 33 and mid 65. Any suggestions?
Where do you fly home from? That might impact advice. My first thought was Lucca, it is still in Tuscany, but a very different feel than Siena and close to Florence if that is where you fly home from. You could also just stay on in Siena and daytrip from there to some of the other towns.
Visit the small towns in between Siena and Florence, on the Chiantigiana. Start with Monteriggioni, San Gimignano and Volterra.
We have not booked a flight home yet. I was waiting to figure out where we will end up closing out the trip.
Honestly, given the short time, I'd pick a hill town or agriturismo near Siena. San Gimignano doesn't really qualify as a "hill town" but it is pretty cool. Staying in town will be more convenient but the agriturismo is pretty fun and unique.
https://www.visittuscany.com/en/ideas/8-towns-in-the-siena-area/