Day Trips to Tuscan Towns from Florence

You've got a great list.

Sometimes I google "images" and that helps me decide where I want to go. Or, a little guidebook research on what to do/see in each place. I've been to all of them (except Greve in Chianti), they are all different. Siena is the most historically important city, and it makes a nice contrast to Firenze (Siena is medieval, Firenze is Renaissance); Lucca/Pisa is a good combination and I love walking the wall in Lucca (the Campo dei Miracoli in Pisa can be seen in a couple of hours if you don't climb the tower).

San Gimignano is a bit overrun with tourists most days, but it's a lovely town with a good collection of medieval towers. Montepulciano is also a nice town, lots of walking on steep side-streets (true in Siena as well).

Train timings for a day trip from Florence to Pisa and Lucca.

RE 3111
Dep 08:28 FIRENZE S.M.N. (Italy)
Arr 09:28 PISA CENTRALE (Italy)

RE 6761
Dep 12:20 PISA CENTRALE (Italy)
Arr 12:47 LUCCA (Italy)

RE 3079
Dep 18:31 LUCCA (Italy)
Arr 19:50 FIRENZE S.M.N. (Italy)

Thank you both :)

Siena and Lucca are two of my favorite towns in Italy. Both unique and wonderful. Pisa is only worth, in my opinion, a half-day to see tower and church. Can't go wrong with either town. Lucca still has its medevial walls around it and a stroll, bike ride, and/or picnic on the ramparts is a wonderful way to spend a day. Siena is fantasic...the unique neighborhoods, the Campo....its wonderful. Enjoy!

Siena hands down as the first day trip choice. Easy by bus and plan to spend the day. The Cathedral is jaw dropping, climbing the Torre Mangia is a must if you can
https://janettravels.wordpress.com/2011/09/18/climbing-the-torre-mangia-at-67/
and if you can't there is access to a high view perch from the Museum (the unfinished wall of the Cathedral (they stopped expanding it during the black plague and never resumed) has easy access and a great birds eye view.) The Contradi (local districts) are interesting to stroll. The Campo is among the most lovely squares in Italy.

Siena would also be my definite top choice for a single day trip destination from Florence and works with public transit easily.
We did the Heaven's Gate cathedral tour (let's you walk inside and outside the roof) and that was very impressive and worth it.
Have to reserve that online in advance.
The Cathedral there I thought inside and out is more impressive than the Duomo in Florence which is a bold statement and the Campo Square is one of the coolest piazza's I have ever seen. Shopping between the 2 on the medieval streets is cool too.

Greve in Chianti and Montepulciano I am not sure how convenient it would be, public transport to those areas I think is more geared toward workers than vacationers. Also if visiting these towns part of the charm is seeing the surrounding countryside which you need a car or tour to do.
If you really want to see countryside and wineries and find a tour group doing so, then combine one of these 2 areas for one day and Siena for the other.
Have not been to Chianti but have been to Montepulciano. if you do go to Montepulciano make sure the tour includes the countryside between Pienza and San Quirico which is a short distance from Montepulciano; that is probably the most famous and beautiful countryside in all of Italy.

You don't have time for a 3rd day trip and not sure it is even worth squeezing in 2 of them but
Lucca and Pisa work as a good combo if you need a 2nd one that works with public transport.
I would rather see San Gim or Volterra I think than either one but don't think you could combine the 2 successfully so would be picking one and in that case rather see both Lucca and Pisa.

It's worth mentioning how hot it is in August, really exhausting just to walk around. And it's vacation month in Europe, so Siena (yes, a great destination) will be even more crowded than usual, which is very crowded. You can't see all of Siena in one day, so it's an ideal day out from Florence. But even the fans with sprayers on them don't cool down the sidewalk cafe's enough.

Consider advance purchase of a comprehensive Siena card (sorry, I failed to do this, so I can't help you sort through the options) so that you never have to wait on a line to buy a ticket, but only maybe wait until enough people leave ... .... xxx .... for you to enter. And some must-see locations, like the Cathedral, will be sold out for the day when you get to them.

If you are not that much into art and museums, maybe you should consider another sleeping location and daytrip to Florence one day? (Not my choice, just making a suggestion for thought. Especially since the Duomo is so close to the railroad station.) That way, you might have a pool to jump into after a sweltering day of sightseeing.

https://community.ricksteves.com/travel-forum/italy/florence-for-15-nights-in-january

Thanks, everyone. We already have our accommodations booked in Florence although they are changeable. We chose Florence because we do want to see a few things there and we got some feedback that it was a good place to base ourselves because of the easy access to public transportation. I think right now I'm leaning toward doing a guided wine tour to Chianti or San Gimagnano and then a day trip to Siena on our own.

If you want to see a bunch of places via public transit or take tours from, which it sounds like you do then Florence is the perfect location for your stay.
I just think August is not the best time of year to go, but often you have to work with what you have.

The big debate for you is if it is worth doing 2 full day trips and leaving only a day and a half for Florence which makes everything rushed or do 1 day trip and then not feel rushed. If you skip the museums in Florence your 1 and a half days there is more realistic but keep in mind those day trips are often draining especially in August heat.
Ideally you would have 5 nights and then easier to take 2 full day trips out from that.

Yeah, unfortunately we don't have other options timing-wise next year and the trip is already booked regardless (flights etc.) Hopefully we can plan our 2018 trips more strategically--we're aiming to travel in March and September of 2018.

Anyway, the only museum we plan on visiting in Florence is the Accademia, and I can't imagine that we'll spend more than 2 hours tops there.

You will love Florence, it would be hard not to, the fact it is crowded is really the only thing negative about it.
Very small, easily walkable with a good portion of it being totally free from cars.

Great food, very clean, safe, amazing history and architecture. The city looks like it may not have changed much in hundreds of years and even if you are not the museum and art type the whole town is basically an open air museum to enjoy.

On our recent trip we did not go into any of the museums (we took our 3 year old daughter) and only had 2 full days to explore the town. That still felt rushed and while we saw the highlights we wanted to see we did not have much time to just relax and take it all in. There is much to see in a very compact place.

We thoroughly enjoyed the Walkabout Florence Best of Tuscany day tour. It's a long day, but well worth the time and €. It hits most of your high points in a very efficient way. It was neither too fast for slow me, nor too slow for our 5-year old grand daughter.

When I did a day trip to Lucca and Pisa (way back in 1989), I saw Lucca first, and was very glad I did. I got to Pisa in the late afternoon; the souvenir vendors were literally packing up, the crowds had substantially thinned, and the marble of the buildings in the Field Of Miracles (where the Leaning Tower is) looked lovely in the afternoon light. So, I'd definitely do them in that order.

That's a great tip Harold.
Gonna remember that one.
Thanks.

I agree with Harold. And have lunch in Lucca rather than around the Campo in Pisa.