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3 Week September Italy Itinerary & Transport Advice

I am planning a 3 week trip to Italy in September to celebrate a milestone anniversary and birthday. We've been to Italy once, spent most of our time in Rome, and visited Venice & Milan, then took the train to Switzerland. Amalfi coast is #1 on my list for this trip, and I want to see some northern parts of Italy that we saw on our train ride. Plan is to fly in on a Friday, which would arrive Saturday morning-early afternoon and depart on a Saturday, so we really have 20 full days. Can I get some opinions on my proposed itinerary and if you think we should rent a car for all or part of this trip? We really loved our time in Switzerland and wanted to combine again with this trip, but I just don't want to use a week of our time there, so I'm thinking the Dolomites, which I assume we'd want a car for.
1. Leave on Friday and arrive Milan early Saturday, rent car drive to Dolomites
2. 5 nights in Val Di Funes area of Dolomites
3. 3 Nights Lake Como
4. 3 Nights Cinque Terre
5. 4 Nights Florence w/ a day trip to Pisa/Lucca and another day trip to some other Tuscan towns
6. 5 Nights Positano w/ day trips to Capri and drive the coast to some other towns
That leaves one free day/night at the end of our trip to get to our departing city, either Naples or Rome depending on flight availability. Does this order and duration at each location make sense? Would you keep the car rental the entire time or only use for Dolomites? Driving around Tuscany and even Amalfi coast seems fun, but is it in reality or would that just add stress? It seems like it would cut down on travel times, but is it worth the possible frustration of having to navigate, pay tolls, park, etc. Any other areas/regions we should swap in? I'm trying not to over plan, but want a solid travel plan in place to maximize the time we have there. We won't be into visiting any vinyards/wineries and not big on visiting lots of museums. We are more into enjoying beautiful scenery, love mountains and easy to moderate walks/hikes, I love anything water related, my husband likes to visit churches, and of course we want to eat and drink all the things.

Posted by
4922 posts

I would very, very, very strongly (have I emphasized that enough) recommend that you do not attempt the drive from Milan to the
Dolomites on your arrival day, when you'll be jet lagged. That could be dangerous. Instead, head to Lake Como by train first for a few days.

I think 3 nights in CT might be a bit too much, given that you'll also be spending time on the AC. I'd take a day from there to add to your Tuscany time.

As for car rentals, I suggest reading some previous threads about having a car on the AC or in Florence. Not the best idea. Some Tuscan towns like Siena, Pisa, and Lucca are easy by bus or train. So you may only want a rental for the smaller hill towns; maybe only for a day or 2. Don't forget that Florence itself deserves a few days. Getting around the AC by car during tourist season is a royal PITA. There are buses and ferries that do a good job. But if your trip there will include Capri and Pompeii, I'd recommend staying in Sorrento, for ease of transportation, and visiting the AC towns as a couple of day trips.

Posted by
877 posts

Personally, I'd skip CT entirely. Consider Bologna instead and daytrip to Ravenna and/or Parma.

Posted by
6 posts

Why skip CT? I feel like it's a must see, at least for a day, but curious why you would skip it.

Yes I considered staying the night wherever we land to just relax for the night and get some sleep. Might fly into Verona instead. Really just depends on flight availability when I get ready to book. I wanted to do Como after Dolomites to break up the amount of driving/travelling that we'll be doing in a single day. That seems like a very long day of driving if we have to drive 4 hours or so to Milan to drop off a car and then another 3+ hours on a train to CT.