Sample itinerary - Italy 13 nights
 

Planning a trip to Italy for late September/early October. Plan is to tackle 3 areas - Venice, Florence/Tuscany, and then Rome. Here's what I've come up with so far:

3 nights Venice
5 nights Florence (day trip to Pisae and day trip to Siena)
5 nights Rome

Could I possibly cut Florence down to 3 nights and do 2 nights Siena? Or should I keep as is? (Really want to do Pisae)

Of course - you can do whatever you want. Why not?

Not everyone does exactly the same thing in Florence (or any other city). What are you interested in seeing there? The usual museums? If you go through the highlights of Florence and think you'd need more than three nights there, spend more time there. Pisa is an easy day trip from Florence, but it will take 1/2 a day, and with three nights you'll have only two full days.

Why not four nights in Florence and one in Siena? Siena is a beautiful town but you may not need that much time there.

Lucca is so close to Pisa, you could easily combine the two for a really lovely day.

A lot depends on what your interests are. I could easily go back to Siena simply to see the cathedral and the wonderful floor mosaics if nothing else. Ans Pisa is, IMO, worth a trip as people will tell you "there's much more than the tower." However, that tower can be absolutely mesmerizing when you see it in person.

Both places are fairly easy to get to from Florence, too.

Florence is a city that you could easily see in a day, if you visit only one of the smaller museums and maybe one of the church/museums. If you have a passion for Renaissance art, two weeks might not be enough. For a brief visit, especially for someone who is not intimately familiar with Renaissance art, I would recommend skipping the Uffizi, which is highly focused on religious paintings of the Italian Renaissance. It has all of the great masters of that period, so if you appreciate these artists, you could spend days there, comparing masters to their apprentices, the techniques of one decade to those of the next decade, and contemporaries to one another.

So, in order for us to help you allocate your time, we need to know more about your interests.

I've stayed in Siena multiple times (and Florence). It's easy to take a few day trips from Siena, but with only two nights, you wouldn't have time (two nights = one sightseeing day). Like Florence, the historic center of Siena is very compact and walkable (Siena is hilly, Florence is flat).

From Florence, you would take the Sita bus to Siena as it drops at the edge of the historic center. From Siena to Rome, you would take the Sena bus (about 10 departures daily). It's as fast as the train, but doesn't require changes like the train does. It also picks up at the edge of the historic center (train station is further away).

http://www.sena.it/Home/78-1-en.html

If you decide to split your stay between Florence and Siena, a day trip to Pisa can easily be done in half day from Florence (or even less if you only want to see the tower). Pisa is an hour by train. You could leave Florence mid-afternoon, see the tower, have dinner and take a late train back to Florence (last train is 10:30). IMO Pisa is more crowded in the mornings or mid-day than later in the day as most tour groups and bus tours aren't staying in the area.