1st time to Italy and need help with itinerary please!

What a great trip you will have! A couple of thoughts, though. I think your direction from Rome to Venice, south to north, is good. (Actually in September you can go either way.) Flying into one city adn out of the other is good planning. 5 nights Rome is perfect! Might be a good place to book your cooking class. Check Ron in Rome's website for cooking classes in Rome. If you are not big art/museum people, skip Florence, stay in Siena 3 nights, and add a night each to CT and Venice giving you 3 nights each CT, Siena and Venice. (Some will say this is sacrilege, not seeing Florence, but only you can decide.) Take the train to Orvieto early the morning you depart Rome, see the Duomo, have lunch, continue to to Siena by train. From Siena you can take a wine tour with Tours By Roberto (a Rick Steves' pick) on one day, and the second day you can rent a car to take a tour on your own. A nice drive would be Siena, Montepulciano, Pienza, Montalcino and back to Siena. That's a VERY full day, about 3 hours of driving, and maybe 4-6 hours in stops. Next to the CT. Drive to La Spezia and drop the car. Its about a 3 hour drive. Hop a train to your preferred CT town. CT to Venice is about a 6 hour train trip so leave early. You'll still have two full days in Venice since you would stay three nights. Buon viaggio!

Amber, I'd suggest visiting Rome - CT - Florence - Venice, in that order. There's a direct train from Roma Termini to La Spezia which takes ~3H:45M, so that will minimize the travel time. From La Spezia you'll transfer to the small local train for the trip to whichever of the five villages you'll be staying in. The trip from there to Florence is also relatively easy, and from Florence to Venice is VERY quick. Happy travels!

You really don't want or need a car in Florence. Potential for big fines if you violate the ZTL zones. You might want to check flight times for departure from Venice. sometimes leaving from Venice Marco Polo can mean a very early flight. It is not impossible to get to the airport at 05:30 but there are better ways to spend your last morning in Italy. So take a look at how a Rome/Venice arrival departure compares to a Venice/Rome arrival departure. My other suggestion would be to trima night from Florence and add it to Venice.

My wife and I just returned from Italy. We had a wonderful time! I would recommend that you rent a car in a small town and drop it off in a small town. We took a train from Rome to Orvieto and picked up the car in Orvieto. We spent several days driving around to the hilltowns in Tuscany. We then dropped our car in Chiusi and took a train from Chiusi to Florence. Hertz has locations very close to the train stations in both Orvieto and Chiusi. Also, get a GPS device to use when driving in Italy! It is so easy to get lost even with the best paper map. Enjoy your trip!

Amber, I agree with the others about driving in Florence. We just returned last night from 8 days in Italy. We spend three nights in Rome, three nights in Venice and drove between them stopping off at Tivoli, Assisi and Padua. If you are not real art museum fans, cut Florence off the trip and maybe day-trip into it. BTW, my wife and I became great art lovers after visiting the Uffizi. If not for the museums, Florence is a large cluttered city. Driving in it is folly. I'd do 3-4 days in Rome, 3 days in Venice and string the other sights together with a combination of train/ car as your nerve allows. I drive in anywhere that isn't Florence or Naples. Don't spend so much of your time in the big 3 that you miss the rest of Italy's story, the smaller villages such as Assisi and Siena. So if you're not art lovers, bag Florence as a base, but I'd still visit the Uffize and GDA and see if it doesn't make dent in your art appreciation. If you are more the food/ wine travelers, then I'd rent a car for as much of the trip as I can, and wander the villages. BTW Assisi, drivable, Cortona, not so much. My wife and I left Rome, rented a car and drove to Tivoli (Hadrian's Villa). We wanted to picnic at the Villa, but never found a market. We climbed the hill into Tivoli and had a great picnic lunch of sandwiches, fruits and cheap wine while looking down from Tivoli.
That was our kind of food/ wine experience. Enjoy

We went to Rome for 8 days of our 15 day trip 2 years ago. We had a very nice apartment near Termini, on Via Napoleone. The Piazza Vittorio market is a large open stall market inside an old Milk processing factory. It is just south of Termini. Tomatoes to die for. We would go out to dinner at night and the next day I would try my hand at repeating what we had the night before. It was great, and really helped keep the cost under control!