My friend and his gf are going to Verona for a wedding which happens to coincide with her bday. She wants to do lake como for her bday the first week of September before they go to the wedding and invited a bunch of our friends along.

The plan is lake como sept 1-4, then they go to the wedding and everyone meets up in Siena about five days later before we all go to Rome and Amalfi. So there's a group of us that have about five days to get from lake como to Siena and we need some suggestions.

All of us have been to Florence and lake como many times, along with portofino, Milan, Genoa and Pisa so we would like to go to some places we haven't been. None of us have really done Tuscany outside of Florence. We haven't been to cinque terra, Verona or bologna or basically anywhere in between. I would prefer trains but we have all rented cars before so we don't mind doing that if it's easier to get to some off the beaten path towns.

So the question is if you had five days to get from Como to Siena, are there some must see places we should look into?

Montalcino, Volterra, Pienza are some smaller towns that my family has enjoyed. Montalcino & Pienza are south of Sienna so not sure they'd work for you. You would also need a car to get to most of the smaller towns like these in Tuscany.

I stayed with some friends in Chianciano Terme a few years ago and used it as a base to visit Montepulciano, Montalcino, Monticchiello, and Cortona. We loved every minute and Chianciano Terme was the perfect base. There were no other tourists there, so it felt like we had the whole town to ourselves in the evening. We rented a bike one day to get to Monticchiello....beautiful ride.

Not sure if it'll be relevant, but I got some pretty good suggestions here:
https://texags.com/forums/54/topics/3450196

One of our accidental highlights in the area of Pisa/Verona was the Ferrari Museum in Maranello. None of us are super into Ferrari but it was really cool. We talk about it 20 years later.

wife and I stayed here for a few nights on our honeymoon trip. incredible place in tuscany.

https://www.spaltenna.it/en/home

If you're into cars, the Pagani factory is awesome

Honestly it's worth checking out the southern regions like Puglia and Calabria. Insanely affordable, absolutely gorgeous (the coasts are incredible) super friendly locals. Bari is a very underrated city, and every Italophile should throw themselves into Naples if given the chance!

I rented a car a few years ago in Italy and drove through and visited Venice , went all around Tuscany, Pisa, and Cinque Terre. I would highly recommend doing this, especially Cinque Terre.

I love, love, love Siena and would spend my time there but I have not traveled extensively throughout the area, so take it with a grain of salt.

We did much of your itinerary last year. Tuscany is awesome. We splurged for a guided driver for a couple of days. Public transportation is almost non existent in the smaller towns.

Cinque Terre is awesome; largely not luxurious. Park in Spezia and take the train in.

Have fun!

My wife and I are staying in Riomaggiore for a couple of days in August.

Agree with the comments on including the Cinque Terre. However, I'd consider making Portovenere your base of operations - it's a great little picturesque fishing village with several easy hikes with great views. Easy train rides from there to whichever town fits you the best (i.e. Monterosso for a true beach experience, or my favorite, Vernazza, for scenery).

Please quit mentioning Portofino - I want to keep it as my little "secret". It can easily get overrun on cruise ship port days, but is definitely my favorite place in the world to spend even part of a day. I went there 5 straight years, at one point, and am eager to get back (haven't been there post-COVID), but I hope it doesn't lose its' quaintness and charm due to being "discovered" by a new horde of visitors.