Regarding Livorno, this port sits right on the western side of Tuscany which is full of interesting places (although most are not very close to Livorno). We have spent many months exploring Tuscany and could easily spend another 6 months in that region. From Livorno you can easily go to Lucca by train, visit Pisa (we do not love this place) or rent a car and start exploring the smaller towns in Tuscany (such as San Gimigano, Volterra, etc etc), go to Siena, take a drive along the Chianti wine road (S222) etc. And that is just for starters in this very interesting part of Italy. As to Florence, it took us 4 visits and finally a several day stay to really start to appreciate the depth of this great city. We are always amazed when folks say they have been to Florence for a few hours and have seen it all!