First Time Italy Trip

I think your idea of taking your time in each place is spot on. I've only been to three of the cities you list: Rome, Florence, and San Gimignano. San Gimignano is beautiful, but pretty small, so four nights may be a lot. Consider going to Siena at least for the day from SG, if you aren't already planning to.

Florence is glorious. If you plan to take a day trip or two from there, I suggest spending a few days less in Rome and adding that to Florence. Going to Venice for the day from Florence is doable, but my travel mates who did that (I didn't) said it was a very long day. They didn't regret it, but wished they had more time there.
Excellent idea to build in relaxation time before heading home!

We rented car in Florence and went to Volterra and Montepulciano and I think Orvieto. Spent several nights in each. Beautiful drive. I think more days in Florence. Florence is my personal favorite.

Although Venice is (only) a two hour train ride from Florence, I wouldn't recommend doing it as a day-trip. The best times to be in Venice are early morning an late evening while there are no "day-trippers." I would suggest taking a few nights from other locations and spending some quality time getting to know Venice.

The sheer luxury of almost a month for your initial trip to Italy just begs--to me anyway--the opportunity to spread out some more. In September it's still high season but maybe not as crazy touristy. If I had that kind of time, and it were my first time in Italy (and I was comfortable driving there--not everybody is), I might do this:

Rome 7 nights
(train to Venice)
Venice 4 nights
(train to Florence)
Florence 5 nights
(train to Chiusi, get car)
Montepulciano
or
San Gimignano 4 nights
(drive to Salerno, drop car, bus/ferry to Amalfi or Positano)
Amalfi/Positano 4 nights
(train to Rome)
Rome 3 nights

There are many other permutations of this itinerary, possibly farther north in September as farther south can still be quite warm, but you should be OK. It's great to 'set up shop', so to speak, in a place like Rome or Florence, but to me 5-7 days is perfect unless you're going to live in a place for a month.

And while I've never been to either, Montepulciano and San Gimignano seem to be somewhat similar, but that's your choice of course. I just would like to see different stuff, you know? Rome, Florence, Venice---are all cities but all very different, maybe except for the throngs of tourists in high season, although Rome seems to absorb tourists better than the other two. And the Amalfi Coast--on a 27-night trip--should not be missed. From there you could easily see Pompei, which is fabulous.

Whatever, again it's truly a luxury to have this much time--enjoy your planning!

FWIW, and if I had 27 nights, on my first trip to Italy, I'd run with similar to Jay above.

Arrive Rome
Train to Florence - 5 nights
Train to Venice - 4 nights
Train to Lucca - 2 nights
(pick up car in Lucca)
Drive to San Gimignano - 2 nights
Drive to Montepulciano - 2 nights
(drive to Chiusi, drop off car)
Train to Amalfi Coast/Sorrento - 5 nights
Train to Rome - 7 nights
Depart Rome

I can't imagine going to Italy as long as you are going for and not seeing Venice. Venice is unlike like any other city in the world. It deserves at least 3 nights. There has been some good suggestions on what and how long to spend in different cities. I think most everyone who has spent time visiting Italy will recommend you visit Venice. You definitely have the time to include it.

Some things to consider...
- Shorten Rome, so you can include a stay in Venice.
- Consider Amalfi Coast over Fregenae, pinching a night from San Gimignano.
- Spend your last night at Ostia, near Fiumicino

Rome - 8 nights
Venice - 3 nights
Florence - 4 nights
Montepulciano - 4 nights
San Gimignano - 3 nights
Amalfi Coast - 4 nights
Ostia (near Rome Airport) - 1 night

We will be traveling to Italy for the third time and this fall we will also be there a month. I agree with several suggestions like shorten Rome to a week and add time to Florence and Amalfi coast is a must. We got our car right at the Rome airport and then returned it before we began our week in Rome as you do not want a car in the city. We stayed in Apt in Trastevere which is a great area lots of restaurants. I never ever visit a major city without doing a tour- this is money well invested and even though it's our 3rd visit to Rome we will do it again. I always try to do it the first or second full day in the city sold know where we may want to go back and spend more time. I highly recommend Miles and miles
( milesandmiles.net). They are family owned and operated and only do Italy. We prefer it as it was just our family- we did the whole day Rome tour they offer a couple. The first half is in a Mercedes van and then you can do the other half walking Ancient Rome or do the Vatican and St Peters. They buy tickets ahead so they also have ability to have you skip all the lines. I would avoid doing Saturday. Francesco is fabulous as our guide and we will book with him in the fall. We also did their half day. 9-1pm walking tour of Florence- a must. Again try to do it your first full day. Highly recommend Pompei. We lover the boat trip to the Blue Grotto and Capri for a day. ( on the way to the Amalfi coast or back would make sense). Enjoy!!!

With 11 nights in Rome why not go to Naples? This is a great food city! Capri etc?

Venice is a must with the amount of time you have!

Unless you are running for Mayor, 11 nights in Rome is too long! 7-8 at most.

When I am back tracking to fly home, I stay 2 nights in departure city at end this gives me
time to see things from a different perspective on second entry. Maybe stay a week in Rome, head off, see the other towns/ cities then return 2 nights before flight gives you breathing time between travel and long flight home.

Have a wonderful trip!

I spent two weeks in Rome the second time and did not find it too long at all, and don't be enticed by anyone else's idea of a 'must see' if it does not fit into your desired schedule. Venice and CT are very long day trips from Florence, too long for me, as there is public transport to some of the more famous wine villages close by. I'll stump for staying in Fiesole during your stay in Florence.
If your main reason for staying in San Gim is for San Gim itself and Volterra, base in Montepulciano and take a nice, long day trip. Yes, I am arguing against myself here, but if you take the back roads bright and early it's a beautiful drive. (I dislike changing accommodations as much as long day trips). If you intend to see Lucca and Pisa as well, then San Gim is a good spot to base in.
Having said all that, I would A) pick up the car in Rome and head to Montepulciano, stay 10 nights, drop off the car in Florence for 4 nights, then back to Rome by train for 13 nights to take it easy - yes, it is a big, busy city, but you can make everything slow down to your own pace.....OR B) pick up the car in Rome, head for Montepulciano for 7 nights, then onto one of the villages in Chianti for 7 nights (Greve, Panzano, Barberino, San Casciano) which have public transport into Florence and have easy access by car west to San Gim, Lucca etc.
I had to look up Fregenae, I do not see any benefit in staying there for 4 nights. Phew.