Italy for 30 days help

Lucky u to spend a month in wonderful italy.
As a freq traveler to Italy I suggest:
1. If u have time unare close to Lugano switzer.land.
Take ferry to Mennagio then bus to Lugano.
2.u could benefit having a rental car for the Dolomites, it is wonderful.
3.enjoy everything espec after the cruise passengers leave.
4.if u have time u could go by bus from Florence to Siena, easily done.
5.perfect
6 Rome reserv now for Borghese , otherwise u may not get tix.

Have fun.

Lovely trip, sounds great! I don't have any strong recommendation of where to add your 3 days, because as far as I'm concerned it's pretty hard to find anyplace in Italy that's not worth visiting.

As for transportation, I think you could do the entire itinerary with train & bus, but you might enjoy having a car in the north. Personally I would not want to deal with a car from your 3rd destination (Venice) onward, so I think your "should I rent ..." questions are right on target. The trick will be figuring out where to pick up and drop off your rental.

As you have outlined your trip, I think picking up a rental car in Milan to go to the Dolomites and returning it there on you way to Venice makes sense. All your other destinations are served by train ( except Amalfi coast, but a rental is a liability there).

As for you extra 3 days, Naples is a consideration, or if you want to not have one more move , add them to Rome

MXP to Lake Como- we always book Davide Guerrerofor MXP to Bellagio, based in city of Como. Or train from Milan to Varenna, then ferry to any other location if desired.
Rent a car for the Dolomites. Recommend Hotel Grones in Ortesei.
Venice to Pisa to Florence-train
Florence to Amalfi Coast-train to Naples, then driver.
Amalfi Coast- to Rome, driver to Naples, then train.
Add two to three days to actually stay overnight on Capri, much, much better experience either before or after your Amalfi Coast stay. Recommend
family owned La Minerva. If you can’t get a reservation there, try to stay on the pedestrian pathways between Giardini Agosto and Punta Tragara. You will be looking at the water and away from tourist mobs. Beautiful. If you only go for a day, also walk between the two points listed above, visiting both.
Instead of Capri, you could also add the three days in more rural Tuscany between your time in Florence and Amalfi Coast. Many choices of towns and villages in Tuscany including Siena, Pienza, Montalcino, Panzano, Radda, or Castellina. You should have a car if you stay in Tuscany to visit out of the way villages.
Have a great trip!

Your itinerary looks good, although it would be better to visit Pisa as a day trip from Florence rathering than going there and then backtracking to Florence on a travel day. I suggest adding 3 days in either rural Tuscany or Umbria between Florence and Amalfi Coast, best done with a car that you could pick up in Florence and drop off in Sorrento. I second the suggestion for a car for the Dolomites. Everything else can be done efficiently using public transit (trains, buses and boats).

Thank you everyone for your replies, they are excellent and very helpful!

You MUST get out into the country in Tuscany/Umbria. Stay there! The best part of out trip. We rented a car in Florence and stayed out in the country and then You could drop the car in Chuisi (sp?) or if it's Hertz in Orvieto and train to Rome or you could drop the car at Tuburtina train station closest to the highway in Rome and the walk or taxi or other transport to your hotel.

I agree with Joe 42F, rent the car in Lake Como and drop it in Venice.

Add a night in Como, the Dolomites and the Amalfi Coast. Think in terms of nites, not days.
4 N=3 days.

I assume you are spending the night in Milan since your plane arrives at 21:00. Then renting a car the next morning?

hey cee_rawd
where are you flying in from? have you booked all your hotels already and have you asked for late check-in at bellagio or varenna lake como? do as suki says. that cab ride from airport to lake como will cost you $$$$$. use rome2rio.com that calculates for you. train to milan centrale then a cab to your hotel. long day and night hope you can check by midnight -1am. don't plan much next day with jetlag. sent you a message, log-in upper right corner will say unread message.
aloha

@ Judy B so far the night of our arrival will be in Bellagio. I have coordinated with our accommodation and they are aware of our late night arrival and they have made preparations for us. I figured a cab would be best, although expensive, I’m not too sure how late the train runs to Varenna and then the ferry to Bellagio. Or if I could even train to varenna and can to Bellagio. But I just expected for there to always be taxis waiting at the airports. I would rent a car from the lake como area and drop off at Venice

@ princess purple I will be flying in from Qatar. I just checked out rome2rio.com, thanks for the suggestion! Are the price estimates accurate? For a taxi it says USD 100 - 130 and Uber USD 237. Why is Uber so much more??

I have coordinated with our accommodation and they are aware of our late night arrival and they have made preparations for us

Given this circumstance, I would ask your lodging for a suggestion/recommendation on how to get there at that time of night.

Taking a car from Varenna to Bellagio is not practical.

Spending the night in Milan is probably the best solution, given your arrival time.

@ Joe32f do taxis from the airport not typically operate late at night? Because I would just taxi from Malpensa Airport to Bellagio

I have no 1st hand knowledge of taxis at MXP. As it is a major airport I would expect taxi's would be available whenever there are air passengers there.

This site estimates taxi fare at $140-$180---https://www.rome2rio.com/map/Milan-Malpensa-Airport-MXP/Bellagio
I would not be surprised if there were a surcharge for the late hour

Here is another source --https://booking.suntransfers.com/booking?step=1&iata=MXP&hash=2f79132c-acd6-11e8-8a5f-06210fdb04d6

As I mentioned earlier, I think your landlord may be a good source for transport info.