Suggestions for road trip Italy

We have always rented our cars from autoEurope. They will stand behind you if there are any problems with your rental car.

Bob, this is a VERY short trip, I don't see it being possible (or at least reasonably so) without cutting something. You won't be going anywhere on the 28th if coming in late at night (from where?) and Malpensa is a long way from Tuscany. You would have to be in Naples on the 1st for a morning flight. That gives you 3 days between Malpensa and Naples: barely enough time for Tuscany, and no time at all for the Amalfi Coast. Consider as well that daylight will be short.

In addition, I see from another post that you are planning on flying into Porto (Portugal) on the 11/5 and flying out of Lisbon late at night on the 7th with this road-trip schedule:

5th: Rent car in Porto.
Porto, Douro valley (Pinhao)
6th: Coimbra, Obidos, Peniche, Sintra, Lisbon
7th: Lisbon

This is also a pretty aggressive plan. What are you doing between flying out of Naples on the 1st and into Porto on the 5th?
Editing to add: you will need an IDP and credit card for renting a car (you didn't have a card for your Salzburg trip 3 years ago.)

Totally agree with Kathy

Best use of your very short time would be to get to Florence by train on 10/29 and just stay there for 2 nights
Train from Florence to Naples late afternoon 10/31 for your morning flight on 11/1

You are trying to cover too much ground

You might consider doing an all day guided bus trip from Florence that takes you to Pisa, SG, Siena

Yep, I'd just get to Florence by rail on the 29th and day trip from there. An organized tour may be the only way you could cover enough of the Tuscan locations on your list in a (short daylight) day. Have you made your flight reservations yet? If not, could you fly to your next destination (what is it?) from Florence? It's a waste of time to go all the way to Naples if the coast does not fit reasonably into the plan.

I can't even begin to wrap my mind around doing all that in three days. Can you change either of the flights? If not, I highly recommend changing your wishes for this trip! You can have a lovely three days, or a mad dash.

As well, happening in Lucca over your dates:

https://www.europecomics.com/events_cpt/lucca-comics-games/

This is from some years back but....
https://www.cbr.com/think-san-diego-gets-crowded-look-what-happened-at-lucca/

I personally would scrap this one: sounds like it's going to be overrun.

How was Switzerland?

Yep, I'd just get to Florence by rail on the 29th and day trip from there.

Me too, but I'm afraid they are going to get the car and drive directly from MXP to Tuscany on the 28th.

I think they want to wake up in Tuscany of the 29th: since the last high speed train to Florence departs from Milano Centrale at 20:10, driving would be the only option. Otherwise I see no reasonable reason to pick the slower and most expensive mean of transport between Milan and Florence.

Thank you everyone for your replies.
@Dario I land at MXP at 10 30 PM. I plan on staying somewhere not too far from MXP (probably somewhere enroute florence) as its night time and I dont want to drive all the way upto Florence. In the morning on 29th, park the car in a parking lot in Florence and explore the city by foot from there. And probably go to Pisa, Lucca the same day if time permits. And stay overnight enroute Seina or in Siena. Then explore Siena and a vineyard on the 30th. 31st morning I plan to leave to Amalfi coast and spend the night there and on 1st November morning go back to Naples airport (11 50am flight).

I have driven in Spain previously and also in the USA. But this will be my first time driving in Italy. Europcar has quoted 275 euros for 3 days (airport to airport) for an automatic transmission car.

Please suggest guys.

I am happy you are not driving after the flight, but I am still wondering why on earth you are wasting vacation time to drive between Milan and Florence through the Apennines when there is a train running at 250 kph under the mountains (as they say on TripAdvisor). Are rental prices in Florence higher than in Milan?

Your driving times between those cities seem a little optimistic, if you are using only Google Maps you'd better use also viamichelin for planning. The idea of leaving luggage in the trunk without worries all over Tuscany, Lazio and Campania is extremely optimistic. Anyway It's your choice.

In the morning on 29th, park the car in a parking lot in Florence and explore the city by foot from there.

There is a parking called Villa Costanza outside Florence on the A1, you can park there and get on the tram to the city center. If you departed from the Hotel close to MXP at 8:30 AM, if you made no stops along the way and you did not get lost on Bologna's ring road... you'd enter this parking at 11:40 AM. Then there is the time needed to reach the city center. If you took the 7:40 AM high speed train from Milano Centrale to the Center of Florence you'd be there at 9:35 AM. Or at 10:35 AM if you took the 8:40 AM Italotreno's train.

Very kindly, Bob, but if you try to drive from somewhere near Malpensa to Florence - which kill most of 1/2 a day - sightsee Florence, drive to Pisa, then to Lucca and THEN to somewhere near Siena in one (short daylight) day, you won't see or experience anything at all. Florence alone deserves at LEAST a full day to do any sort of justice at all. What are you planning on doing there?

Keeping the Amalfi Coast is just not practical, and is a long drive from Siena; figure on killing another 1/2 day.

As said earlier, you could have 3 days just in the Tuscany area - and those would STILL be rushed - or 3 just running place-to-place without really seeing them at all. And I'd pay attention to Dario's caution about having all your stuff in your car while you try and do all of this.

@Dario and @kathy. Thank you very much for your replies. I was not aware of the safety issues with the bags in the car. As you guys said, I'll consider the train option. Will it work out well if I get a train pass for Italy for 3 days ?

option 1:
1.) 28th Night 10:30 Pm once I land at MXP, either go to Milan central by whatever mode of transport that is available at that time and stay in a hotel there. And take the 8am train to Florence. Or stay back in MXP airport nearby hotel and then take early morning 5 40am train to Florence.

2.) 29th and 30th Stay in a florence hotel. Explore florence, pisa, luca and siena if possible using public transport and return back to florence.

3.) 31st morning take a train from florence to napoli central or salerno.

4.) 1st Morning 11 50am take flight from Naples airport.

option 2:
1.) 28th Night 10:30 Pm once I land at MXP, either go to Milan central by whatever mode of transport that is available at that time and stay in a hotel there. And take the 8am train to Florence. Or stay back in MXP airport nearby hotel and then take early morning 5 40am train to Florence.

2.) 29th store luggage in florence. Explore florence and then leave to pisa in the night by train/bus. Stay in pisa overnight
30th explore pisa. Check out from hotel and go to siena/nearby place and stay overnight.

3.) 31st morning take a train/bus from siena/nearby place to napoli central or salerno.

4.) 1st Morning 11 50am take flight from Naples airport.

Please suggest which would make sense and be economical.

Bob-
Neither plan makes sense but of the 2, Option 1 is the better choice.

No need for a rail pass. Just get point to point tickets as you go. Both Trenitalia and Italotreno have easy to use apps.
Trenitalia for fast and regional trains, Italo for fast trains only.
https://www.trenitalia.com/content/tcom/en.html
https://www.italotreno.it/en

Where are you flying FROM and where are you flying TO?
If you land at 10:30 and that's a big IF- you might as well stay near Malpensa then head out early in am to Florence.
Stay there for 2 nights and day trip - you'll cover more ground if you book a guided tour rather than try to do it yourself. Since you are saving a huge amount by not renting a car put that savings into a tour if these are must see places.
Walks of Italy has a Tuscany tour and there are others.
https://www.walksofitaly.com/florence-tours/tuscany-day-trips-from-florence/

Fast Train from Florence to Naples will take about 3 hours. You need to be IN Naples this night as your flight is before noon. If it is going to US you need to be at airport 3 hours preflight, if to another European city then 2 hours is probably enough.
Salerno would give you better access to Amalfi coast but it's too far to be on a night before a flight. Train strikes, delays etc and train only gets you to Naples central where you wil still need transport (taxi ) to the airport. Too risky.

You need to spend some time with Google Maps and see exactly what you are trying to do and how you are covering way more ground than is possible in such a short amount of time.

If you can change your flight to fly TO or FROM Florence- that would certainly help. As it is you are spending a lot of time on trains, not much time actually sightseeing these locations.

Not really sure what the point of this trip is? It looks like you are planning something similar in Portugal- where will you be in between these 2 locations?
IMO- This Portugal plan doesn't make sense either
https://community.ricksteves.com/travel-forum/portugal/portugal-trip-suggestions-8da95698-d8b3-4664-bb36-ff8ddbf1de6d

Thanks for your reply. I will go with the option of staying 2 nights in florence and explore florence one day on my own and another day take a day tour via some tour operator to pisa and siena. With respect to amalfi, I'll probably take the early morning speed train to naples from florence and then take a day tour via a tour operator. The next day at 11 50 I have to take a flight to paris. will spend 4 days there and then to portugal.

With respect to Portugal, I land on 5th morning from paris in porto at around 9am. So, I have the entire 5th, 6th and 7th until 7PM, before I takeoff from lisbon at 9PM. Lisbon, porto and sentra are the major places I intend to see. Would you recommend renting a car ? Is it safe and not too difficult to drive around in these places ? Or would you suggest public transport and day tours here too ?

You won’t need or want a car in Porto, Lisbon or Sintra

Spend 1 night Porto
Train to Lisbon -2 nights
Day trip to Sintra from Lisbon on Day 1 I guess so you don’t miss your evening flight

Really not enough time for all of those places

Here is my issue, Bob.
You haven't told us what your interests are. Why go to Florence if you don't know what you want to see there and/or how to do that? Same for anywhere else on your list. You might also end up on the Amalfi Coast on your scant 1/2 day to pouring rain and it doesn't look at ALL like the pictures you've seen of it. You'll barely be able explore the coast with the few hours you have to give it. There is a reason people spend 3-5 nights or more in the region.

So what do you what to do? What do you want to see? What do you want to experience on this trip? Again, very kindly, but I'm not seeing anything beyond blowing though Destination A, B C. D, etc. just long enough to snap a picture and nothing else...and maybe that's all you wish to do. If so, it's your trip so that's fine! It's just that you're being advised on more than just this forum that you're trying to do too much, and will spend more time in transit than much of anything else.

(Edited)

The OP's posting history tells me that he has already done a whirlwind, famous sights, tip-of-the-iceberg, hit-the-highlights trip to Europe in 2019 and now wants to do a similar trip in Italy so he must have enjoyed this style of traveling. I say "Why not?" even though it is the exact opposite of how I like to travel --- up to a point, people get to do what they want in the available time, right?

My only concern, based on having spent a total of 331 days traveling in Italy by car, train, and bus, is that the more tightly scheduled the trip is, the more an unlucky event or a mistake in planning can derail things. We just got back from 30 days in Italy and had to deal with (on arrival day from the US) a partial train strike that had us standing on a crowded platform with tickets from Rome to Civitavecchia in hand for an hour only to be finally told the train was cancelled. It rained all day on three days we had outdoor day trips planned. I caught a bad cold that wrecked our plans for two other day trips. The days and hours that several museums and restaurants were open according to Google or their own websites were not correct. It took us more time to find a parking space for the day in Genoa than it did to drive from Chiavari to Genoa. We experienced every day, as many times before, that the time Google or Rome2Rio says it takes from one place to another can be wildly optimistic, and we now try hard to take that into account, but were late to appointments and lunch reservations a few times.

Still, we had a great trip! But it was partly because we had 10 times more days to work with than the OP does, so a problem here and there didn't matter so much. I am not at all advising the OP to slow down or to attempt less or to adopt a different style of travel that many of us prefer, just to make as realistic a plan as he can. It does help to write it all down instead of keeping it in one's head (where it's all too easy to breezily think things like "Then we'll go to Pisa!")

Guys I am staying for 1 night in Milan, 2 nights in florence and 1 night in naples. For, florence would there be need of public transportation to explore the city or by foot is it possible ? Also, while in florence I plan on going to pisa and another place in tuscany (siena probably with a visit to one wineyard) if time permits. Is there any availability of any travel pass for 24 hrs so that I can cover these places or is it better to buy a bus/train ticket on the go ?

In naples, I plan to take a trenitalia train to salerno and then a sita bus to amalfi and ravello. So, train tickets I am planning to buy here at the station individually for the to and fro journey. And for sita bus ticket,an unlimited daily pass if it would make sense ?
Please suggest guys.

For, florence would there be need of public transportation to explore the city or by foot is it possible ? Also, while in florence I plan on going to pisa and another place in tuscany (siena probably with a visit to one wineyard) if time permits. Is there any availability of any travel pass for 24 hrs so that I can cover these places or is it better to buy a bus/train ticket on the go ?

You won't need any sort of public transportation in Florence. If you have time to go to Pisa, just buy train tickets: there is no pass. You will not have time to do that AND go to Siena; if you choose Siena then it is best by bus. But I would stick with Pisa, which you can visit in 1/2 day if you are quick (and you will have to be quick).

In naples, I plan to take a trenitalia train to salerno and then a sita bus to amalfi and ravello. So, train tickets I am planning to buy here at the station individually for the to and fro journey. And for sita bus ticket,an unlimited daily pass if it would make sense ?
Please suggest guys.

I do not see how you could achieve this with only one night in Naples. Considering the time needed to drop off your luggage along the way in Naples, it will take about 7 hours from your Florence hotel to Amalfi, and public transport back to Naples takes another 2-3 hours!
For this to have any chance of being feasible, I would stay in Salerno, as long as your flight out of Naples is not too early in the day...

@balso Thanks for your reply. My train from florence to naples just takes 3 hrs and reaches naples at 9am. So why i thought of doing amalfi from naples.

For Italy, consider Umbria: Perugia, Assisi, Spoleto, Spello and Orvieto.

My train from florence to naples just takes 3 hrs and reaches naples
at 9am. So why i thought of doing amalfi from naples.

Except that Salerno is much closer to the Amalfi Coast than Naples. There's a 07:05 train that will have you there by 10:30 with one change in Rome.

Question? In this thread you note that you're flying out of Naples to Paris on Nov. 1 at 11:50 AM. But in your Amsterdam post, you note that you're arriving at Schipol (Netherlands) on the 1st at 11:05, and flying out again (to Paris CDG) the next day (Nov. 2) at 13:55pm. Which one is it?

https://community.ricksteves.com/travel-forum/netherlands/amsterdam-public-transport-suggestions

Assuming you are traveling light I would suggest that you take train from Florence to Salerno
Then take bus along Amalfi coast all the way to Sorrento
Then Circumvesuviana ( or ferry) to Naples for your last night

I think that is better use of time than going to Naples first.

Thanks guys for the replies. I have an early morning 6 30am flight from naples to amsterdam on Nov 1st. Hence I am staying in Naples. Initially my flight was at 10am and then got cancelled and got reassigned to a 6am flight.

Thanks guys for the replies. I have an early morning 6 30am flight from naples to amsterdam on Nov 1st. Hence I am staying in Naples. Initially my flight was at 10am and then got cancelled and got reassigned to a 6am flight.

Oooh that's rough... you definitely need to stay in Naples then.
I guess that at this late stage, you only have one night available for the area?
I am also guessing that it is too late to reschedule and fly out of Florence or Pisa instead, dropping Naples altogether?

Keeping everything as it is, I think that the Amalfi coast is too ambitious. It takes too long to get there from Naples, and back.
How about heading to Capri instead? It is a stunning island, and if you play it right you would have the whole afternoon there.