Itinerary help!

The itinerary looks fine. I don't know what your plans are for ground transport, but based on what you have I would rent a car for Tuscany between the end of the Rome visit and the start of the Florence visit. In other words I'd rent a car in Rome the day you get out of town (no car needed in Rome) and drive to tuscany by car. with it you can take day trips to small towns and countryside. Then you would return the car when you arrive in Florence (no drop off charges even if different cities, as long as same country). A car is also a hassle in Florence, therefore return it as soon as you get to Florence. If you decide to do Florence day tripping from your castle in the Chianti or wherever between Florence and Siena, then keep the car a little longer and don't bother to check into a hotel in Florence. But if you are a person who gets bored in the countryside estate surrounded by olive trees, cypresses and vineyards (you are from Chicago so you must like cities), then stay in Florence a couple of nights. It's a lively city, like Rome.
After Florence (Tuscany), since you are going to Switz. I would not bother with the Cinque Terre. I would take a train straight from Florence to Milan and from Milan I'd take a train to Varenna (on lake Como). I would stay either in Varenna, or Bellagio (across the lake from Varenna). 3-4 nights aren't enough for both the Cinque Terre and Lake Como. you could do a couple of nights each but it's about the same type of environment. Quaint fishermen villages on a shore (sea shore or lake shore). Depending on where in CH you are going afterwards, you may want to consider Lake Maggiore instead of Lake Como.

I love C.T., but would suggest Lake Como, Varenna. Would also suggest making reservations now to get the exact accommodations you want.

Jennifer, Your proposed Itinerary looks reasonably good, however a few comments...... > If you have the time, I'd suggest 4 nights in Rome. There's an enormous amount of things to see there and lots of history. Keep in mind also that you'll be jet lagged for a few days, so won't be up to full "touring speed". Have you allowed for your two flight days in your planning? > With only 3 nights or so in Tuscany, using one location as a "base" and then taking day trips is the method I'd choose. Siena or Florence are both good places to consider. Which place to choose will depend on which locations you want to visit in the area. > Using a rental car for visiting smaller towns is prudent, as public transport is sometimes "challenging". However, a couple of important points to kee in mind. EACH driver will require the compulsory International Driver's Permit, which is used in conjunction with your home D.L. Also, you'll need to be VERY careful to avoid the dreaded Zona Traffico Limitato areas, as expensive fines will follow (which you'll only learn about several months after you've returned home). The ZTL areas are especially prevalent in Florence. > Although Lago di Como is beautiful, with 3-4 nights my suggestion would be the Cinque Terre. There will be more to do in the evenings, some good beaches and a good choice of day trips possible in that area. Also, as you mentioned "lounging, eating and wine tasting".... - try the local Pesto in the area where it was invented
- try Schiacchetra, a dessert wine unique to that area For your stay in the C.T., it would be a good idea to get accommodations booked SOON!!! It would help to know where you'll be going in Switzerland after Italy? Good luck with your planning!