In November 2016 my husband and I went hiking on Via Valeriana trail near lake Iseo in Italy with our baby (at that time 11 months) in a carrier.
Via Valeriana is not a very long trail, just 24 km, but very scenic and diverse - you see mountains, forests, waterfalls, and of course beautiful views of lake Iseo. It's suitable for beginners and even more - beginners like us with a little baby. There are several small towns on the way, where you can enjoy really charming old Italian way of life and of course food+coffee - the best in the world in my opinion!
I wrote in details about this trail and our experience of it on my blog and also put many pictures. If anyone finds it useful, you can read all about it here.
And of course please let me know if you have any questions, or if I can be of any help!
Wow! It looks and sounds like you were able to head out on an incredible adventure! Do you think that you would be willing to map out the route on Hiking Project? We would love to get the route added directly to the database!