We’ve nailed down our itinerary except for one last item… We want to do one day trip from Florence, with a goal of combining a fun walking town, perhaps some touristy site (like the leaning tower of Pisa) and perhaps most importantly, an incredible lunch. I think we’re trying to limit the trip to 1 hour by train from Florence but are otherwise open. Any suggestions? I know a very open ended question but hoping someone recommends something that just grabs me immediately 
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Probably not as specific as you’d like, but here’s what we did.
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@small_h and I did a day trip by train from Florence to Pisa about 30 years ago and it was pretty much exactly what you want. There’s more than just the Leaning Tower to look at. I remember that a cecina, a pizza-like flatbread made with chickpea flour, was the thing to eat (street food, not “incredible lunch”). Interestingly, the chickpea-flour pancake is also a thing in Genoa, where Mr. travelmad478 and I had it last year; it’s called farinata there.
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And life is still too short to eat bad gelato.
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There’s such a thing?
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You wouldn’t think so, but yes. Or at least, not great gelato.
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I found this thread helpful when planning.
We did a day trip by train from Florence to Sienna - it was fabulous, including a really good lunch right on the Piazza del Campo (no, I don’t remember the restaurant). Great sightseeing.
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Siena is fascinating, I think. Architecture and history especially so. Been too long for me to recommend any restaurants though.
If the OP is interested in Siena, I’ll share that I “met” and arranged a virtual tour of the city with this tour guide during the no-travel days of the pandemic. Our virtual tour then was so informative and fun that I can only imagine the in-person experience would be excellent.
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I love Siena and that would probably be my choice, although it’s been many years since I’ve been there and we always stayed at least a couple nights because there is so much to see.
Arezzo is another option, less visited, with a number of good restaurants and stunning Piero della Francesca frescoes among other sights. There is a train from Florence that takes about an hour–also longer journeys, so if you go there , make sure you get the fast train. La Torre di Gnicche (traditional), Le Chiavi d’Oro (more modern, upscale)…I stayed several days pre-pandemic and ate well.
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Go to Collido and visit the Pinocchio Park and the Butterfly Gardens.
Then drive south for about 20 minutes and get a reservation at Serendepico.
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I’d go to Monteriggioni and stop at Bar Orso which has fabulous panini, especially their porchetta. Also their cappuccinos are fabulous.
From there you are clost to Siena or to my favorite plase to explore, Monte Oliveto Maggiori. You can go to Conte Matto for a wonderful dinner after MOM
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Siena, as mentioned a few times already, or else Bologna for something different, also in terms of food. Another option is going to the countryside. There are a lot of food tours available from Florence.
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Arezzo, Siena, pisa lucca are all really nice train destinations. Renting a car for a day enables you to do a itinerary like Dean suggests into the Tuscan countryside although increased traffic has made the whole area less bucolic than in the past; for example parking in Siena was very difficult on our last visit. Bologna even is a relatively short train ride from Florence and is a super destination for culture and food. Last time I looked Pisa was not a great food destination and the meals we’ve had there in the past have wound up being pretty simple but it is one of a kind for Romanesque architecture and sculpture.
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Whoa.
I need to know more about this.
Was this, as I am imagining, a Zoom group call of some sort?
Do tell.
Yes. Unfortunately-
Personally, I would rather have bad gelato (and, yes, I agree, there is such a thing) than really really good ice cream.
And I’ve had some bad gelato.
Chiming in to say that Bologna could be another great option.
You are confusing.
Exactly!
A group of my friends expressed interest in a virtual tour of some sort. We’d traveled to Italy in the past. I’d read that some of the guides associated with the Rick Steves tours had pivoted to offering online tours during the pandemic, and I thought that could be a good way to connect with a reputable guide. So I was able to arrange a tour especially for our group.
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