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suggestions for self-guided tour (via train) of San Gimignano, Siena, Chianti, Monteriggioni

We'll be in Florence for a few days, and are considering doing our own tour on a big holiday (all seems to be mostly closed in Florence that day, and few guides available). We have a guided tour of a winery a different day, so I'm thinking of trying to visit a few small towns nearby via train. I'd appreciate any advice/suggestions (alternatives are welcome). We're happy to ramble around and see the sights, and I would try to prebook a lunch at one of the stops (recommendations also appreciated for that). Thanks so much!

Posted by
1026 posts

Hello fdfoster, and welcome to the boards!

The complication you're going to find is that much of small town Tuscany is not well served by train. Some of the larger towns such as Arezzo and Siena can be reached by train but the smaller classic "wine towns" are not. There is a train stop labeled 'San Gimignano' but don't be fooled it is actually the stop at Poggibonsi and still a good 8 miles from the town of San Gimignano proper.

Siena is served well from Florence by both train and bus - the bus delivers you more centrally - and is well worth at least a day of exploring and has many good restaurants.

Arezzo's old town center is certainly smaller than Siena's and is much less touristy but it is also a charming little town full of modern shopping, hilltown verticals, ancient buildings, a great piazza and Tuscan countryside views at the top.

Yon can connect Arezzo and Siena by bus (1.25 hours) but it would take some coordination and planing to get from Florence to Siena to Arezzo and back to Florence in a day but the trains from Arezzo back to Florence do run later than the trains from Siena.

Cortona is 1.5-2 hours away by train and you need a further bus to get up the hill but it routinely voted one of the most beautiful towns in Tuscany. Cortona is mostly famous recently from being featured in Under the Tuscan Sun.

If you want the small wine town experience Greve in Chianti is reachable by bus in about an hour from Florence. Greve features tons of good Chianti regions wines but lacks the old world buildings of some place like Montepulciano.

To the north is Lucca with it's charming old town center and walls as well as Pisa with its obvious attractions for a short train trip but these may lack the Tuscan charm you are looking for. I really like Lucca but it doesn't say 'Tuscany' to people who are thinking of rolling hills and vineyards.

To go completely off piste Bologna is about 40 minutes from Florence by fast train and is Italy's traditional food mecca. It is a big city rather than a small town but would easily supply a day's exploration and a ton of great restaurant options.

Hope that helps some, making choices with some many great options is always difficult.

[Addition - I just found this old bookmark - this may help: https://www.wanderingitaly.com/maps/tuscany-rail-map.html ]

Have a great trip,
=Tod

Posted by
8 posts

Tod has some great suggestions. Easy to day trip to a few of the towns he suggests, many of which are within an hour, but it would be tricky to string them together. There's the added plus tha the train will drop you in town and not in the middle of nowhere. We absolutely loved Arezzo (Piero DellaFrancesca's restored Legend of the True Cross at the Church of San Francisco is worth the trip standing alone). Also just an hour to Lucca, where there are ready bike rentals to ride atop the wall that rings the city, another great experience. Assisi is 2 hours away, but in reach if you get an early start. Pisa can fill a day as well, and again just an hour away. You'll see alot of the countryside out any train window. . .

Posted by
2 posts

Thank you both so much! I will definitely check out Arezzo, and the other towns you suggested. Even getting an introduction to a couple of additional towns will be a bonus, and we can happily spend the remainder of the day in Florence.