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Best route to go Italy trip 2027

Hello
I am planing a trip to Italy this will be my second time. :) Trying to get an idea which route is best for the areas I want to visit with no self driving. My plan is to fly from New Jersey to Milan for direct flights, from there I would like to go to Tuscany area love wine and the country feel so I want to base myself in a location to tour wineries and love walkable towns and shops and Aperitivo. but also easy to tour other city in Tuscany region. Definitely do not want to stay in Florence already been. then we want to go to Puglia area and from there Sorrento base to explore Amalfi Coast then Rome and home. So basically What is your suggestion with direct trains to each location Car will pick up at each train. only one night in Milan to rest then Each area 4 nights then 2 in Rome . What towns to you suggest to stay in and have restaurants and all the above I am looking for?

Posted by
9048 posts

Tuscany-base in Siena otherwise you will want a car
Rome
Puglia
AC
Fly home from Naples

Direct flight to Rome on arrival would make more sense than Milan unless you have reason to stay in Milan

Posted by
12123 posts

For your stay in Puglia, I recommend Polignano a Mare, a lovely seaside, small city.

Posted by
17605 posts

Tuscany is closer to Rome than Milan, so I would fly to Rome instead of Milan, which is quite a distance from Florence (Tuscany). You don't seem to be interested in anything north of Tuscany, so Rome makes more sense. The majority of non stop flights from the NY area to Italy are to Rome.
If you plan to see Rome, then leave it for last before you fly back from Rome.
Alternatively you can also fly back from Naples, if you don't care to see Rome or if you plan to see Rome upon arrival.
There are non stop flights from Naples to Newark, NJ with United, but they are seasonal (late spring/summer only). So if you plan on that make sure they are available on the date you return.
From Tuscany to Puglia is a long way (like 500+ miles). If you go by car it's a good 9-10 hour drive. By train it is about the same, unless your departing point is Florence, which has high speed train. But still about 7 hours to Bari. There are flights to Bari, but only from Florence or Pisa.
To visit Tuscan towns, a rental car is definitely a plus, as many towns have limited bus service. Since you don't want to bother with Florence, Siena is the best base if you plan to use buses to visit Tuscany. If you rent a car, then you can stay anywhere.
A car in Puglia is also good to have. If you plan to rent a car for Tuscany, you might as well drive to Puglia and keep it for there too. I know it's a long drive, but the alternative is two separate rentals, which may not be convenient or even economical.

I suggest 4 nights in Tuscany, at least a week in Puglia, 4 nights for Sorrento/Amalfi Coast, at least 3 nights for Rome.

You could possibly rent a car for the whole trip and not bother with anything else. Obviously you should try not to have a car while in Rome. A car while in Sorrento/Amalfi Coast is also not necessary, so you could return it in Sorrento when you arrive, and go to Rome by train.
If you pick up a rental car at one location and return it to another there may be some one way drop off fees. They vary depending on the rental car company, and on the distance between the pick up and drop off location. I hear the highest one way fee will be less than 130€, but I don't know for sure. I've never paid more than 15€ in the recent past, but pick up and drop off were in the same region. I rented in Milan and returned in Florence a few times before Covid, but in those days they didn't charge me. I think they figured out to add that extra revenue now.