Two friends and I have just booked flights for ten days in Italy in late September/early October. We are flying into Rome and out of Florence. In those ten days we are planning to go to Rome, Cinque Terre, Florence, and some of the towns of Tuscany (which ones yet to be determined).
We are planning to spend two nights each in Rome and Cinque Terre, and the remaining six nights in Tuscany, possibly splitting them between Florence and an Agriturismo. Because we are flying out of Florence, I am thinking of going from Rome to Cinque Terre - is this a good decision, since we are now going from our most southern to our most northern spot? Are there good train options? I looked a bit on the Trenitalia site but was a bit confused (and that was the English site!) as to the differences in prices and times, but it looks like we can get to La Spezia fairly easily and then switch trains?
As for the time in Tuscany, I would like to spend some time in Florence, some time touring some hill towns, hiking, eating, drinking, and learning about the food and wine. There are so many towns to choose from! I am thinking maybe a day trip (tour) from Florence to the Chianti region, with stops in Siena and San Gimignano, while we are spending three nights in Florence, and the other three nights spend at an agriturismo in the Montalcino/Montepulciano/Pienza area? Does that seem like a good plan? I would like to hear your feedback.
As for getting around, I am interested in renting a car but my friends are hesitant - they think it will be too difficult and stressful. But from what I've read, as long as you stay outside of the city, it's not too bad, plus it's difficult to get everywhere without one unless you want to figure out the bus routes. How strongly would you recommend having a car? Also, I am a frequent traveler with Hertz, but all domestic. I believe I can use my points to cover the actual rental cost. Any experience in using Hertz in Italy?
Thanks for your help!