Help with italian itinerary (plus add-on portugal)

Slow down and enjoy life.
I love Portugal, but I would recommend spending more time in Italia.

I have been to Cinque Terre and the Amalfi Coast, and I feel like they have some basic similarities that would lead me to not put both in one itinerary with limited time, so you could consider getting your hiking/scenery fix while you are on the AC, but I do realize you had a desire to return to CT. I would go ahead and read up on Sorrento versus the Amalfi Coast to determine which would work better for you. Naples has a million things to see--read up somewhere like the Blue Guide to see what you would be interested in before deciding how many days you need.
We all like a different pace of travel, but this seems fast paced to me. I think it is definitely overambitious in the Umbria/Tuscany portion. It is never bad to have all of your options sussed out, I just would not count on getting to half of those places.
The Portugal portion might break up your flight home, but all those days could sure be put to good use in your Italy itinerary. If you keep it, I would look for flights to Porto so you don't have to break up the Lisbon portion so much--all that back and forth is probably not necessary.
Good luck!

A few thoughts:
- Travel logistics to and from the Amalfi coast are difficult. To reach the Amalfi coast you need to get to either Sorrento or Salerno from Naples and then driver, bus or ferry to the actual coast.
- If you want to visit Pompeii and/or Herculaneum and Paestum do this from Naples where it is an easy Circumvesuviana train not from the Alamfi coast location. Pompeii is also easy to reach from Sorrento or Salerno but becomes an all day struggle from the actual Amalfi coast.
- If you rent a car in Orvieto I believe you're limited to Herz which may or may not work out for your drop off plan. People also rent in nearby Chuisi (or Chiusi-Chianciano where the train station is to be exact) to get more rental options. Chuisi of close to Montalcino, Montepulciano, Pienza etc.
- Be sure to check your "Tuscany" locations because Tuscany is a big area. Montalcino, Montepulciano, and Pienza are in southern part nearer Orvieto than Volterra which is more in north. It would be at least 2 hours each way from Volterra to the southern towns one way which is well outside my limit for a relaxing day trip. I would suggest a southern location and then a northern location if you want to explore the whole area.
- Check your drive times in general for your plan. Google maps times should be considered a minimum time and not used for tight planning. The roads are small, windy, and subject to several types of delays.
- If you're planning on driving anywhere in Italy get your International Drivers License before you go and read up on ZTLs and always check ZTL websites before driving into a small hilltown to avoid expensive tickets. Also there is zero tolerance for drinking and driving so plan if wine tasting is part of your itinerary.

And my standard advice for Tuscany - slow down and enjoy it. Part of the appeal of rural Tuscany is slow pace of life dictated by the seasons and the beauty of the countryside. Spending all day driving from one beautiful location to the next on a tourist schedule is only some of the real appeal.

Have a great trip!
=Tod

Heartily concur with hiredman, especially on Tuscany.
On the AC though, we (youngish couple at time of visit, like to walk) really did not find it that onerous to get to Pompeii from Cetara, which is at the mainland end of the AC (near Salerno). We took a bus to Vietri (in actuality we walked when we missed the bus, just go with it) and a train to Pompei, where we walked to the site (15 minutes). It was a long day, but we returned to a chill village with excellent restaurants.I realize it would not be the choice for many, but it is "doable" for those wanting to compress their time to an AC village (I agree coming from Positano or Amalfi is too much of a time suck). You do have some wiggle room in your itinerary, and it is of course easier to come via train from Naples or Sorrento to Pompeii, so this is just something to consider as you fine-tune the plan.
On our other days in Cetara, we took the bus to Minori/Maiori/Amalfi (there was no ferry when we were there, that is improved now) to access trailheads, so I did not find three full days, four nights too much at all. We headed south after and saw Paestum from a different location, but staying near Salerno allows you to also reach that sight if you are interested (recommend--the temples are impressive).

Your itinerary in Portugal is very short. You didn't include much time in Lisbon or to see the amazing Douro River Valley.
I suggest skipping Portugal this time (go back when you can spend two weeks there).

You need more that two nights in Florence.

Do you plan to visit Pompeii, Sorrento and Capri while in the Naples area?

Looks like a fun trip! If you haven't already, I suggest you check on this website Rick Steves recommended itineraries for Italy and Portugal. With that said, I think yours is fine. My experience driving in Italy was it was liberating, a bit scary and more expensive than I hoped.

Happy travels!

In regards to your Portugal section, I would suggest flying directly to Porto. I'm not sure that you can do that from Florence, but it does look like you could from Pisa. I would probably rejig my trip to try that. Your time in Portugal feels rushed to me otherwise. If you can, then you could have Porto 2 nights, stop to see Coimbra on way by train to Lisbon and then 3 nights ( 2 full days for Lisbon)

I realize now that it is bagnoreggio-Civita and that it is one town, not two. I don’t see that we are taking too much on in Tuscany/Umbria as towns are close together and maybe we will just go to Assisi, cutting out Perugia. I also say that because I looked back at our itinerary 9 yrs ago when we did some of these same towns and at that time we were seeing 2-3 towns per day and we didn’t feel like we were real rushed at the time. I also do see the merit to splitting the stays up in Tuscany and maybe staying two nights in volterra/san gimignano area and then another two nights further east and south near montalcino/pienza/montepulciano, visiting massa maritime on the way from volterra???

I do like the idea of flying into Porto rather than into Lisbon, and then spending most of our extra days around Porto area since we have seen Lisbon and Sintra. We could fly from Pisa to Porto but I don’t see any direct flights on Skyscanner or kayak and flights are long. I’ll keep looking. Does anybody have experience with flying on RyanAir or easyjet??

I can see where Cinque Terre and Amalfi coast might be sort of similar and if our friend doesn’t join us we might cut out Cinque Terre altogether. If she goes, I kind of want her to experience it as it is so awesome and she has not been to Italy at all. And since my husband and I have not visited Amalfi, I threw that in for us. Some of these towns are duplicates for my husband and I but are more for our friend and we loved them so much that we don’t mind going back. Plus there are new places thrown in for our benefit as well.

Thanks for all the suggestions. Gives me some food for thought.

Just a few thoughts on your plans:
If you're flying from the US to Rome, and plan to take a train directly to Naples, just be aware that flight arrival times are so hard to predict, I would wait until arrival and plan to buy a full fare train ticket when you are sure of your timing.

I've been to Naples twice, the first time I drove in to one of the neighborhoods where we had reserved gated parking in our apartment. Parked the car on the way in, and didn't touch it until the drive out. Obviously, Naples driving is as bad as they say. I'm a native Boston driver, with a lot of NYC driving experience as well as Rome, Palermo, Lisbon etc. Naples was probably the worst (Palermo a close second!) Our second visit to Naples we flew in from Palermo and took the very convenient and cheap bus from the airport to Napoli Centrale station. We stayed just a couple of blocks from the station and spent a lot of time exploring the area. That area is very chaotic, so just be prepared for it. I've challenged myself to 'conquer' Naples - yes, it's gritty and loud, but it's also very alive and authentic, if you know what I mean. We went to Herculaneum for a half day visit using the train, fairly easy.

Thirty two years ago we visited both Perugia and Assisi (before earthquake) as day trips during our weeklong Umbria stay with cars. Both are great memorable places to see. Remember that 2025 is the Jubilee year, so Rome will be quite busy, and Assisi may see more than usual religious visitors as well. There's a big chocolate festival in Perugia in October - I would try to find out more about these to see how they would impact your trip planning.

We spent 6 nights in Florence, March 2023. It should have been 7 nights but we lost a night because our flight from Boston was cancelled. We used the Firenze card, concentrated on all of the museums, palaces and churchase and never really slowed down the whole time. I could easily have spent another week there and still not be bored. Consider more than 2 nights in Florence.

We were in Portugal last year in October. We stayed in Lisbon for 4 nights, then rented a car and spent 2 nights each in Nazarre, Douro Valley and Porto before returning to Lisbon to drop off the car and stay overnight before flying back to US. The Douro Valley was great, but maybe it's too much for your trip. I was disappointed with Coimbra because we picked the one day in October that the university was closed to visitors because there was a big student event/parade. The city was very crowded, parking and driving were a hassle, it was very hot, and we really didn't get to see much of the city because of the crowds. Again, just check the calendar before deciding on a side trip (for me it wasn't worth it, but could have just been bad timing).

We have flown EasyJet a couple of times, and may fly RyanAir this spring. My philosophy when flying those airlines is to pay for every upgrade - your $30 flight will end up costing $130, but it's totally worth it because you don't worry about luggage (they have more restrictions than the major airlines) you get to board early and if something happens, the flex fare means you'll be able to get on another flight, hopefully easier.

Good luck, and enjoy the planning!