Italy Itinerary Help needed please

It looks to me that you have a nice mix of high-intensity places and very relaxing places, with a good distribution of days allotted to each.

Do you know for sure there's a car rental dropoff in Chiusi? A city like Siena is large enough, but most Tuscan and Umbriran towns don't have the big national car rental offices. Orvieto is probably the most popular drop off place for Hertz as the train station is just across the street and they're just a 70 minute ride into Rome Termini.

Hi David
Yes someone else reccommmended Chiusi as a place to drop the car as there is a hertz rental near the station and I have had a quote to drop the car there. I’ll look into other places you suggest too though to see what works
Thanks

Car return is less than a block from the train station in Chiusi.

I like your plan except for Milan; Milan is for me the most "american" of the italian cities, and that is not what I am looking for when I travel to Italy.

I also would not bother visiting Milan. Instead, spend two nights in Verona. If you want to travel around the Amalfi Coast, I’d suggest staying in Amalfi because it offers better transportation options. Other, you plan seems great.

I'm also in the "Milan is meh" camp. Verona is a nice option, it's opera season so a good opportunity for an evening performance at the ancient Roman Arena. I've met people who've done it who weren't opera lovers, they said it's special and they enjoyed it very much. Most people seem to like Padua. There's certainly a full day of sights there. If not, Bologna (after Venice) is another option. It's not as touristy and offers a variety of day trips by train (Modena, Ferrara, Ravenna are just a few).

If you are looking for quiet and relaxing, Vernazza may not be the place. Others of the forum have suggested staying at one of the villages on the Italian Riviera. Do a search of the Italy forum for Cinque Terre before deciding where to stay (or even if to stay there). If you are renting a car anyway, consider keeping it longer and visiting Assisi and Orvieto. Maybe do the "car stuff" before Florence. Then take the train from Florence to Naples or Salerno. Have you driven in Italy? There are some caveats - especially the ZTL's.

The Amalfi Coast will be crowded in July. It's easier to take a fast train from Rome right to Salerno. If you go through Sorrento, you take the fast train to Naples, then the (probably) crowded local train (really an above-ground subway) to Sorrento, then a crowded bus (and there may be a long line) to Positano. From Salerno, you can get the bus to Amalfi, then change to the bus to Positano (again crowded buses and possible lines) or walk a couple of blocks (level and paved) to the ferry pier. I haven't been there when the ferries are running. There may be ferries all the way to Positano and you may be able to buy in advance. However you plan to get to Positano, expect crowding.

Looks like a great trip. If you are taking the time to go to Positano I would recommend another night there. Lots to do and see in the area.

I would skip Milan and add one night to Positano and one night to Chianti,

Thanks so much for everyone's feedback. It is so helpful to have this kind of forum to ask questions! Thank you!

Now, I have another question... if we drive into Chianti region and Val D'orcia, where would we be best to stay for 2 nights before dropping our car off in Chiusi? I had planned on staying in Radda but wonder now whether San Gimignano would be better or further south... and is it best to stay in one spot for the 2 nights rather than moving and just travel around during the days?

Thanks again!

Positano is incredible, but Sorrento is also beautiful and shouldn't be missed, if you can swing it. We took a train from Rome to Naples, hired a car to pick us up from the Naples train station and take us to our hotel in Sorrento where we stayed a couple of nights. We were lucky enough to have chosen a hotel that has direct access to the beach, and it just happened to be one of the best hotels we've ever stayed at in all our years of travel (it's called Maison la Minervetta). We then got another car service to drive us to Positano.
In Sorrento, I booked a guide to take us around Capri, and it was one of the best things we spent our money on. We were so pleased that we hired the same company to do an Amalfi Coast tour which was amazing, and we also hired them to take us back to the Naples train station and stopping on the way to do a guided tour of Pompeii for a couple of hours. Totally worth it.
We also went in July, and yes -- it's crowded -- but the guides really helped us get through places efficiently and quickly while learning so much about each place (they're called Tours of Sorrento). Good luck!

We are just leaving Italy now. Your trip sounds like fun. We discovered both Volterra and Orvieto and really enjoyed them and would stay longer next time. We caught the train from Rome-Naples-Salerno - and took the ferry to Positano which was lovely. Many day trippers were dropped off on top of Positano by their bus and then ferried back to the town they were staying in... might be easier as walking downhill :-).... personally we didn’t rave about Positano as we found it very crowded and beaches are nothing on Australian beaches, and shops v.expensive but we are glad we went there ... my only advice would be pack light... wish we had followed Ricks advice on that just a little more.. but we are managing ... off to Milan then Lyon today ... ciao

I was just reading on another thread about mydaytrip.com - for driving between cities. Might be worth a look into -