The header photo was taken in Val d’Orcia. I purchase it on shutterstock.com and the photo credit is given at the end of this post. Florence works very well as a home base for visiting Tuscany. The only challenge with Florence is parking, if you have a rental car, because rental cars are not allowed in the city center. If you have a rental car, you could spend 2 nights in Florence (only seeing Florence) and 3 night in Siena, using this to day trip to nearby towns. If you plan to use public transportation, then stay in Florence because it is well connected by train and bus to other cities. As for itineraries, take a look at our 2 week itinerary. This covers the places you want to see. You can then add more time into places like Tuscany, Rome, and the Amalfi Coast. And if you haven’t seen it yet, we have lots of info on our Italy Travel Guide. Let me know if you have any other questions. Cheers, Julie

We love to hike, enjoy food, wine, futbol, cooking (my wife has a separate list for art/history/statues/etc.)… but we appreciate both the hustle/bustle of a city and also love the countryside.
Any recommendations you have (or even itineraries), we would happily review with consideration to what a teenager may be willing to see is greatly appreciated.

Hello Michele. Those are all great questions. From what I know, the Cinque Terre will be busy in October but not crazy crowded like it is in the summer. So, I wouldn’t keep if off your list just because of the crowds, but the later in October you can put it, the less crowded it should be. But if you are starting in Milan, it would make sense to do the 5Terre from here to avoid backtracking to central Italy after Puglia. However, Italy isn’t that big and it can be done. Tuscany will be somewhat brown during your visit (we had very similar timing in 2022 when we did Tuscany and then Puglia and then the Amalfi Coast). However, Tuscany is still beautiful. It is different than Puglia so you can do both on the same trip and it won’t be repetitive. The repetitive part will be touring town to town to town. We worried about that before our trip but we still had a great time. If you skip Tuscany and the Cinque Terre, you could go from Puglia to the Amalfi Coast to Rome, which is what we did. It’s kind of the reverse of our Southern Italy Itinerary. You can think about it and if you still have questions, let me know. Cheers, Julie

Hello Joyce. On the How To Get Around Tuscany section of this post, the first thing I state is that having a car is the best way to get around. The train doesn’t go to every Tuscan town and taxis can be expensive, so if you plan to be in Tuscany for a few days and want the freedom to easily visit the towns that most interest you, renting a car is the best way to go. Cheers, Julie