Tuscany in 5 days


We will be in the south part of Tuscany for 5 days then we will spend a night in Siena and on to Lucca (one night) then Cinque Terre for 2 nights. I thought I had planned our time really well but reading your site I am in a full blown panic. There is so much to see and I do not want to miss a moment. We are staying in a farm house in Multepulciano ( 5 nights) i night in Siena(B&B) I would so appreciate your advise.We have a car and we want to see the little villages as well as the big.Assisi is a must and we hope to be there a least half a day. I wish I had found your site months ago!! we are leaving on the 24th of April until May 4th
Thank you very much
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The Tuscan Expert ;-)
Staff member
Ciao Padragain and welcome to our forum!

I am glad you have found our site useful but I really hope we haven't thrown your schedule off! It seems like you have a good plan.

There is so much to see in Tuscany and 5 days is a good amount of time. Tuscany and Italy are best experienced in a slow manner, so it is better to just accept that you will see what you can and not fret about what you don't -- you can always come back for more :).

So if I understand correctly you have:
5 days in Montepulciano
1 night in Siena
1 night in Lucca
2 nights in Cinque Terre

You definitely can do a day trip from Montepulciano to go see Assisi. On your way back, stop in Perugia and that is your day in Umbria.

Then spend a day in Montepulciano, Pienza and Montalcino. Visit the Abbazia di Sant'Antimo right below Montalcino, it is a beauty.
Another day head towards Cortona, stop along the villages you pass on your way there, maybe make it all the way to Arezzo.
You still have 2 more days to see the area, so you can head in whichever direction you want or go back to any of the towns in the area to see them some more. You can head to Siena as well, start seeing the main highlights.

You'll need at least a full day in Siena, maybe the day before your night there so that you can head towards Lucca early the next day. Stop briefly in Monteriggioni just outside Siena. It is a beautiful small fortress village, very charming.

You should stop in San Gimignano, one of the larger medieval towns in Tuscany. It has gotten very touristy but I think it is definitely unique enough to merit the visit. You don't have to stay long, walk along in streets and have lunch there. Then you can continue on your way to Lucca. You can then see it that evening, and continue your visit and walk around the town the next morning. Walk along the walls to see the entire historical center.

As you head to Cinque Terre, just consider that they are small villages along the rocky coast. Wherever you'll be staying there, plan to park your car and then leave it there for those 2 nights - it is much more convenient to hop on the train to move in between each of the towns. Get the "Cinque Terre + Train Pass" to be able to take the train unlimited times, all the villages are just a 4 minute train ride away from each other. By taking the train, you don't have to worry about driving on narrow mountain roads or about parking which is very limited. Cinque Terre is quite different from the Tuscan coast, I think you will definitely like this other side to Italy when you compare it to the soft rolling hills around Montepulciano.

In my opinion, you will have more time than you think you do. Just plan your schedule as you've already done but keep it flexible, so that as you visit one place or the other you can feel fine about doing a little bit less or a little bit more.

Above all else, take it slow, enjoy the good food, gelato and wine and have fun!! :)


Thank you so much for your advise.We did change on stop and that is we are going to stay in Greve instead of Lucca because we can stay at a lovely farmhouse and have a wine tour with dinner.It sounds so awesome so I changed it. We have seen Lucca before so I feel this will be good.
Thank you


The Tuscan Expert ;-)
Staff member
so how did it go?

Ciao Padragain,

So how did the vacation in Tuscany turn out? Wonderful I hope!

I am curious about the farmhouse in Greve with wine tour and dinner - many are interested in something like that, so if you can share your experience that would be great!!

If you share anything else, I am sure the rest of us would be happy to learn from your own experiences. :)