Italy 14 Day Itinerary

This is intense and involves a good amount of backtracking. I'm not sure if you meant you wanted to visit EITHER San Gimignano, Pisa or Lucca or all three in one day. I would choose just one. Consider stopping at Orvieto on the way back to Rome as it is on the way. It will take you a couple of hours or more to get to Pompeii from Rome, but it is a doable daytrip. Good luck!

You are only staying 3 places, which is excellent. I agree with Mockstew that you could stop in Orvieto on the way from Florence to Rome and that is probably a better use of a day where you are not sure what you want to do, leaving another day for "exploring Rome." Play it loose with the daytrip to Pompeii. It would be a 12 hour (or longer) day. Once you get to Rome, you might find you would rather spend more time here.

Are you traveling by car or train? If taking the train, Orvieto is not exactly "on the way to Rome." Fast trains from Florence do not go through Orvieto and take about 1.5 hours. The trains from Florence to Orvieto are regional and take upwards of 2 hours. And you are schlepping your luggage and storing it for the day. Seems easier to go straight to Rome and then day-trip to Orvieto (fast trains are just over an hour).

If you are using a car, you're likely to be better off staying at an agriturismo in Tuscany rather than in Florence. There's not much to Pisa other than the Leaning Tower with its church and lovely baptistry. I'd drop it.

Lastly, I wouldn't go to Pompeii on my last day. I would want to have the evening to "say good-bye to Rome" and to pack. Pompeii is a long and tiring day with hours of travel time and hottest part of the day under the Mediterranean sun with hardly any shade to be had.

Why stay in Florence if you're taking day trips out into the country each day? It might be cheaper to stay outside the city and go from there.