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Itinerary suggestions

We have 4 days to tour Tuscany (not nearly enough, I know) and would like suggestions on possible itinerary which cover at least a few of these towns. We have a car and are staying in Monticchiello at Terre di Nano.

The towns we were interested : Grosetto, Pienza, Sienna, Lucca, San Gimignano, Assisi, Cortona but know we can't cover them all in such a short time. We welcome any suggested itineraries that would give us a good representation.

Thank you for your time.
DiDi

Posted by
508 posts

I love Monticchiello. It is very close to Pienza. When in Tuscany, we always stay in Cortona and it is not too far from Montichiello. I think it would be a fun day trip. I have been to Assisi twice, but I can't remember how far it is from Cortona. I think it is between 30 minutes to an hour away, so it is doable as a day trip. If you go to Assisi, you should consider hiring Anne Robichaud as a guide, she is fantastic. Her website is at annesitaly.com. If you don't take her tour, or if you do a half day one with her, you might be able to combine Cortona and Assisi in one day.

I love Siena too. You can probably combine Siena and San Gimignano in one day trip.

We have not been to Grosetto or Lucca. If you are interested in wine, you could substitute Montalcino and Montepulciano for those towns. Both of those towns are close to Monticchiello and both are very picturesque.

Be sure and drive some on the "strada bianca" or gravel road around Monticchiello.

Posted by
63 posts

Dear Sherry,

Thank you so much for your suggestions. I will share them with our "friends the planners" and hopefully we will be able to incorporate them into our travels.

Appreciate your time.

DiDi

Posted by
479 posts

DiDi,
Siena is a one day trip for sure. That town is so great, you'll want to spend an entire day. You can do Assisi in a half day. But it's in Umbria so it is off by itself. 4 days might not get you everything you're hoping to do. But you'll still have a great trip!

Posted by
63 posts

Thanks Jarrod for your suggestion of Sienna, I really don't want to miss it after seeing Rick Steve's video. We are so excited about this trip.

I think you are right about Assisi being off by itself and we will have to see if we end up squeezing it in. One of the people in our group is really keen on it so I may let him figure it out.

Thanks again & safe journeys.

DiDi

Posted by
705 posts

I agree with Jarrod Siena is a day in itself. I visited it on a day trip from Florence and we called into San Gimignano on the way. It was a pretty full day but I am so glad I did it, both towns are just lovely. I could have spent more time in Siena though and would strongly urge you to allow a day for it. Haven't been to the other towns you mention.

Posted by
63 posts

Thank you both for your suggestions and time. I have forwarded them to the other couple we are traveling with and we have put a day in Sienna into our itinerary.

We will leave the rest open for now until we get there and see how it goes. No need to jamn up the calendar.

DiDi