It's hard to say without knowing the length of your trip. If this is a first trip and you want to see the main highlights of Italy, then you should visit Florence, Rome and Venice, see the top sights in those three places and also take day trips to places around each of those. So from Florence you can visit San Gimignano the Chianti region and Siena. From Rome you could visit Tivoli. From Venice you can spend a day on the lagoon visiting some of the other islands. Trains in Italy are simple to navigate so you can travel easily from one city to another and to other places, and the railway stations in each city are all right at the heart of things. In Florence and Venice, we walked from the main railway station to our accommodation. In Rome we caught a bus. This would make a relaxed three week trip. If you wanted to do it more quickly, you could do it in two weeks but it would probably feel rushed.
Kim Note: maybe ‘relaxed’ isn’t quite the right word! But three weeks would certainly be more relaxed than two. There’s a massive amount to see in all three places, three weeks would give you the highlights.
As well as national e.g. saint's days Italian towns, cities and villages all have their own special events. Google 'Italy festivals october' to see what's happening where...there are plenty of info sites, though do remember that Covid may still be affecting the planning for 2022. 'Best' is solely a matter of personal preference. Without knowing your interests, the length of your stay, your starting & ending points, your mode of travel and a rough idea of your budget it's very difficult to advise. Rome, Venice and Florence are, of course, 'the big three' but there are very few places in Italy which do not have interesting historical centres...you might, for example, consider Bologna, Naples, Bari, Milan, Genoa.....and all have excellent food & wine. Florence is in Tuscany, so I'd advise combining a stay there with visits to Siena, Lucca, San Gimignano, Pisa (much more than just the tower), Fiesoleand any vineyard excursions you might fancy. If you're interested in history, go to Rome (you could spend weeks in that city and still not see all its historical sights and sites). Make sure you take a daytrip by commuter train to Ostia Antica, the ancient port of Rome and a sort of mini-Pompeii. Walk along the Via Appia Antica, visit the catacombs (Rome has several different sets open to the public), make a daytrip to Tivoli by train or bus to visit the Medieval Villa d'Este and the Roman Villa Adriana... And/or base yourself in Sorrento. Eat seafood, drink limoncello, make a day trip by Circumvesuviana train to Naples. Eat pizza in the city where it originated, visit the Graeco-Roman ruins which still stand up to 2 storeys high underneath the historical centre, go to the Archaeological Museum which holds all the finds from the Pompeii sites. Use the same train to visit the superb Roman sites of Pompeii and Herculaneum and drive or use the bus to travel the Amalfi Coast, visiting Positano and Amalfi. Take the ferry or hydrofoil from Sorrento to Capri, Italy. I could go on and on....Bologna for a 'foodie' paradise and the superb UNESCO Roman sites in Ravenna, Milan for its aperitivi and day trips to Como, Bergamo, Pavia....Venice (extremely expensive) for itself and daytrip to Verona, Genoa for daytrips to the Cinque Terre...... The choice is yours..... :-)
Peter Opinions seem mixed on Lucca. You think it's worth a stop?
Mary If you are interested in Roman & Medieval history Lucca is most *definitely* worth a stop. Imo, it's more historically interesting (and much less touristy) than Pisa...and Pisa is far more than just a leaning tower.Those who don't like Lucca probably a) aren't really interested in history and b) want more tourist-focused locations. · (1 like)