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!!