Day Trip from Florence

Pisa and Siena are both simple to get to from Florence. The train is easiest to Pisa, with many regular direct trains to Pisa Centrale. You will have to walk about 30 min from the train station to the Field of Miracles assuming you want to see the Tower etc. - or take a local bus. There is more to Pisa than the obnoxiously-touristy Field of Miracles. If you walk to it from the train station, you will walk through an old university, and you'll also cross the Arno, which while not as picturesque as in Florence still has some interesting buildings along it, if you want to detour up or back a few bridges.

Siena is a more charming town than Pisa in my opinion (not exactly a controversial opinion). Siena's huge main square will take your breath away. There may be direct trains from Florence now (there weren't back when I visited) but the train station may be further from town than where the bus drops you in Siena - and I did take a direct bus from Florence when I day tripped there.

It's really up to you which trips you want to make. I'm not exactly a museum buff, so when I had three nights in Florence, I day tripped to both Siena and to Pisa.

Siena (by bus because the bus station there is more conveniently located). I'd also rank Lucca (by train) considerably above Pisa. Some of the smaller places are more challenging to reach by public transportation. It is often possible, but the ratio of travel time to being-there time may be high. I believe there are bus tours from Florence that combine San Gimignano and Volterra. There have been mentions of small-group tours on this forum as well, but I don't remember the details. Some of them are wine/vineyard-oriented.

I'd look to see what festivals will be held while you're there. Too bad you time doesn't span a weekend, your opportunities for special activities would be higher.

I would suggest taking a wine and food tasting tour in Tuscany. You'd get a feel for the countryside and get to drink some great wine and eat some wonderful food.

Siena is fun to explore. I would choose Lucca over Pisa.

It was in 1989, but it remains one of my best travel days ever. I went from Florence to Lucca, which at the time was quite unvisited. I rented a bike and rode around on the walls overlooking the city, after walking the town itself. Then in the afternoon, I went to Pisa. The tourist buses were leaving, the souvenir vendors were literally packing up, and the marble in the Field of Miracles looked lovely in the afternoon light.

I highly recommend doing this, in this way. Between these cities, you can take buses or trains.

I also did a day trip to Siena; I didn't like it as much as most others do.

Have you seen Rick's videos on these places? That may help you decide which one you would prefer (although you won't really know until after you've been). Here's Pisa and Lucca: https://www.ricksteves.com/watch-read-listen/video/tv-show/florentine-delights-and-tuscan-side-trips and here's Siena: https://www.ricksteves.com/watch-read-listen/video/tv-show/siena-tuscany-wine-country

Don't overlook Fiesole - just a 20 minute bus ride from SMN. Pleasant strolling, nice places for lunch, pretty hikes thru the forested hills, and beautiful views of the city of Florence in the valley below.

Yes, Fiesole is a really lovely town.

Thanks everyone for the feedback! Much to ponder, but exciting😀

It's been 6 years, but the Chianti Tour that we took with Tuscan Trails was truly memorable - two fascinating wineries (one where the Pazzi revolt against the Medicis was planned) and a delicious multi-course lunch with wine. The current reviews are consistent with our experience.

https://tuscantrails.com/daily-chianti-tours

Both Pisa and Sienna are fabulous but if you want a slower, quieter day Fiesole is wonderful. Local bus - ,There is a great Roman amphitheater, beautiful Duomo and other impressive churches. Great market in the square. Lovely views of Florence and the surrounding countryside.

We took the Best of Tuscany Tour through Walkabout Tours Florence and had a wonderful time. The tour went to Siena and we learned so much from a local guide that we wouldn’t know on our own. We also had lunch at a winery, visited San Gimignano and went to Pisa to hold up the leaning tower. It was one of our favorite days in Italy! Hope you have an awesome trip!