Lucca to Cortona or San Gimignano

You specified day trip by train: you can't get from Lucca to San Gimignano by train, there's no train route. When you look at the location of Lucca on a map, you'll see that it's far to the west and that makes it difficult to do what you want to do.You can get from Lucca to SG by bus, but it's difficult. I should mention that I haven't used buses in Tuscany (one of the few areas in Italy where I choose to drive) so I don't claim to know a lot about getting from Lucca to SG by bus. Here's the SITA bus schedule http://www.sitabus.it/sita-toscana/Firenze-Siena08.pdf, it's not the most user-friendly website I've ever seen. By bus, it looks like you would have to first go from Lucca to Florence, about 1.5 hours (which you could also do by train). Then connect to the bus from Florence (Firenze) to Poggibonsi, then Poggibonsi to SG, a total of 1.25 to 2.0 hours from Florence to SG, plus the 1.5 hours from Lucca to SG. That's one way. Sounds daunting. Lucca to SG by car is much easier, if you have a car, about 1.5 hours driving time each way.Lucca to Cortona is 6 to 7 hours train time, round trip--that is only station to station time and does not include the time to get to the station, wait for the train, etc on both sides on both the Lucca and Cortona sides of the trip. Go here to see schedules for Cortonia and SG http://bahn.hafas.de/bin/query.exe/enTim is our SITA bus guru, if I've gotten this wrong then hopefully he (or Ron of Rome, or Michelle of Vicenza, or Claire) can give us better guidance. The SITA bus schedules are an area of mystery to me. One thing I have learned is the Sunday bus service on many routes is drastically reduced.

We used the buses to go from Florence to Siena and it was great. However, on our trip we went from Siena to Lucca by train to spend a day and night there. If I had to do it over again (because of the amount of time we wasted about 3 hours going from Siena to Lucca) I would not have done Lucca on our trip. It was a great place, but not easy to get to. We had a great time, but could have had much more fun if we spent it in Rome, Venice or Florence. Lucca is a great place, but tough to get to any other places except for Pisa or Florence in a timely manner.

Long story short. If you want to explore, it's best to rent a car and stick to towns that are in the area of where you are staying.

We loved SG. It's very medieval and captures the imagination. We were there in October and the crowds were small.

Thank you all for the help! I think we'll keep researching areas a little closer to Lucca and save Cortona and San Gimignano for a future trip :)