Day Trip from Florence

Looking at what you've already done, also reading what you are mentionning about the fact that you feel like you spend a lot of time traveling between cities, why don't you spend 3 days in Florence?
I spent 3 days in Florence last year and even with 3 days, I felt I was on a timer. There is so much to see in the city. You could take the Firenze card, go and visit everything you want with this card. What 3 full days, the pace wouldn't be that heavy, taking also some time to simply stop, relax on a piazza while habing a wonderful Spritz. :-)
Yes Bologna is nice, but I think I'd rather stay a 3rd day in Florence. The museums are some od the best in the world, starting with Uffizi, Bargello, Del'Accademia, Palazzo Pitti, San Marco and so on.
Aside from maybe Piza, I don't see another easy day trip worth going, more than saying this 3rd day in Florence.
Have a great trip, Florence is such an amazing city
Claude

If you've not already been up there, consider a short day trip to Fiesole in the hills above Florence - an easy, and short, bus ride away. The town itself is a charming place for meandering, exploratory walks. The Teatro Romano is a well preserved amphitheater (still used for summer concerts) and is ringed by Etruscan walls.
A nice side trip is the mostly level path from the town out to Monte Ceceri - the place where Leonardo and his crew performed the first experimental test flight back around 1508. There's a little monument with a plaque marking the spot, which in itself isn't much to see, but the sense of being on the spot where it happened is pretty cool if you or your father are aviation enthusiasts. The walk is a pleasant 1.1 Km stroll and passes some ancient caves where, according to local lore anyway, some of the marble used by many of the Italian masters was quarried.
There are some nice places for lunch up there too, several offering sweeping panoramic vistas over the city of Florence.
If you're really adventurous you can ride the bus up the hill and then work off your lunch by walking back down to Piazza delle Cure in the city (about 2.4 Kms). If you tire along the way you can simply jump on the bus to complete your return journey back into the city.

I love spending time in Florence (my husband and I usually spend a week there every other year) but my dad has the "tour program" mentality and wants to see as many different things while he's in Italy as he can, as he figures he'll likely never go back. I will mention Fiesole to him, as I've never even made it there yet, and it's so close. It's definitely an option.

I think Bologna's historic area is a good day-trip target. The center of that area is about a 20-minute walk from the train station, but a city bus should work. Sorry that I don't have the details on that, but I saw a bunch of buses right outside the train station.

Much of the historic district is arcaded, so if you're unlucky with the weather, you have some protection except as you cross the street.

Wendi:

Bologna is more than a day trip. It's a city that deserves to be treated with a longer stay.
This is also true of Siena, which is often relegated to a day trip by those who stay in Florence.

Consider Arezzo as a plausible day trip this time around for you.

Pistoia is a 1/2 hour train ride from Florence, non-touristy, good restaurants, and with nice 12 - 14th century buildings, many of them green and white striped. At least two museums and an art gallery. Known for its chocolate and its surrounding plant nurseries (once a year they turn the center of town into a garden --- I so wish we could have seen that.)

Our favorite thing in Pistoia was the Cappella del Tau, next to the Museo Marino Marini —- it's a tiny 14th-century chapel, frescoed by the School of Giotto. We were told it was discovered by someone renovating his bathroom. It has the kind of slightly goofy late medieval/early Renaissance paintings we like, such as Adam and Eve about to eat the apple even though God is lurking in a creepy way in the shrubs behind them.

The white and green striped St. Zeno Baptistery is brick inside so you can see its structure, which I found very beautiful.

Cathedral of St. Zeno and its belltower, which you can climb.

Museo Capitolare

Palazzo del Comune

Church of Sant’Andrea

stripey San Giovanni Fuorcivitas

And the "living room" of Pistoa, the Piazza della Sala. Everything is very walkable.

4 nights is 3 full days. One day for Siena -- IMHO the two remaining days are not even enough for the highlights of Florence. Surely he will want to see Academia and David, the Uffizi, the Brancassi Chapel of Santa Maris del Carmine, climb the Duomo, visit the Bargello and the amazing Musee San Marco. Florence is incredibly rich in artistic and historic sights.

Acraven, thanks for the info on Bologna. Sam, I agree with everything you've said. My husband and I have been to Siena for the day several times but will stay overnight next fall, as well as Bologna. However, we are limited to a couple weeks for our trip and my dad would like to get a taste for as much as possible while in that neck of the woods. I did mention Arezzo to him. Plus, I haven't been there, either. Nancy, Pistoia is somewhere my husband and I planned on visiting later in the year but if my dad would be open to it, I'm sure it wouldn't break my husband's heart. And Janet, I'll go over this post with my dad. I agree that there is tons to see in Florence.

I would recommend Fiesole as well. Very lovely little town with some historic sites.
Assisi is also great!

You could easily combine Pistoia with Montecatini Terme/Alto. It's only a 15 min train ride between the two, the lower town is filled with fountains, (in the "Liberty style" creating a contrast to the upper town) accessed by the funicular ride to the old town.

I'd visit Montecatini first, ending in Pistoia which has a very medieval center and lots of art. Have dinner here before heading back to Florence.