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Tuscany Itinerary check

Posted by (Phoenix, AZ) on

Hi all, we are starting to plan out our trip in late Sep/early Oct to Tuscany and I'd love some advice. For reference, it's just 2 adults who fairly well traveled and healthy. We've visited Rome, Venice, Milan and a few other areas in Italy. So just focusing on Florence and Tuscany for this trip.

Unfortunately, as we have kids and busy jobs, our time is limited. Also flights are very expensive from our hometown airport so we're flying in and out of Bologna, not Florence. Those are bought although I could change them if it seems absolutely necessary.

Here's the plan so far:
- Arrive in Bologna in early evening, Train to Florence (sleep Florence)
- Florence (sleep Florence)
- Florence (sleep Florence)
- Bus to Siena. Day in Siena. (Seep in Siena)
- Siena (sleep in Siena)
- Rent car, drive Crete Senesi route to Montepulciano. Stop at winery on the way. (sleep in agriturismo near Montepulciano or Pienza)
- "Heart of Tuscany Drive," (sleep in agriturismo)
- Drive back to Florence. Return car and take train to Bologna. (sleep Bologna)

Questions:
-Is Siena really worth 2 nights? Could I shorten this and add a night somewhere else? (like Montepulciano or another town)
-Would it be crazy to swap the second day in Siena out for Sam Gimignano? I'd like to see another town up north. (unfortunately Lucca is too far out of the way)
-Should we do our Agriturismo closer to Siena and sleep in Montepulciano instead?
-We normally do the "farthest destination point first" but does that make sense in this case? It seemed better to be situated in Florence for a few days to get used to the time before driving a lot.
-Any other suggestions?

Many thanks!

Posted by
3280 posts

Is Siena worth 2 nights?

If you get an early start and check into your hotel before noon you need one night for Siena. This will allow you to pick up your rental car the next morning and visit Montalcino which isn’t much before continuing to Montepulciano. Spending a night in Montepulciano would be ideal.

Posted by
7998 posts

Our last trip, we arrived in Siena mid-afternoon, spent one night, and stayed until late afternoon, before moving on. We really didn’t have enough time there on that 1+ day. We couldn’t fit in two days, but I wish we could’ve. Next time, we still have much more to see and do in Siena, and need to go back.

Posted by
11609 posts

I would give Siena two nights. You should see San Gimignano too. Give it a couple of hours.

Posted by
338 posts

Siena is worth 2 nights. I would spend one night in Sam Gimignano instead of the agriturismo. During midday Sam Gimignano is filled with daytrippers, it’s nice during the day, but it’s much nicer in the late afternoon, evening and morning.

Posted by
1937 posts

I agree with those who say Siena merits two nights. You can also minimize changing hotels by staying there three nights and doing the Crete Senesi drive as a day trip. I did that a few years back and visited Montalcino, the Abbazia di Sant'Antimo, Bagno Vignoni, Pienza, Trequanda, and Asciano all in one day, and I got back to Siena before dark. I passed by Montepulciano but didn't stop there, though I probably should have instead of stopping in those last two towns.

Can you switch things around so you visit Siena before Florence? If you're interested in history, this can make your visits to the two cities more interesting. Siena never transitioned from medieval to renaissance, so you can start with the older styles of architecture before you go to renaissance-inspired Florence.

For a more northern town, I preferred Volterra to San Gimignano, but I do suspect San Gimignano would be nicer after the daytrippers (like me) have left.

Have a great trip!

Posted by
333 posts

Thank you all! I really appreciate your responses! I really wish I had a few more days in the area but I guess that just means we have to return one day!

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