Northern Italy suggestions
 

We will be visiting Italy for the first time in September, doing a guided tour (Tauck) for 14 days and ending in Venice early October. This is our first guided tour, but chose it to see all the highlights (Amalfi, Umbria, Rome, Cinque Terre, Florence, Venice). We will be staying an additional, low key week at the end. Our tentative plan is to rent a car in Venice, perhaps make a stop in Verona for a few hours, possibly staying in Sirmione on Lake Garda for 3 days, then to Varenna for 4 days. We will possibly go up into Switzerland for a day trip. Because we want the flexibility to stop along the way, we are thinking car rental vs. train. We are just in the process of booking flights, and are looking at the best options for flying out of either Venice or Milan. Your thoughts on these plans are welcome, as well as any hotel or restaurant suggestions.

I'm not sure you are going to see much on such a compressed tour. I think you can see the town of Amalfi in a day, but certainly not the Amalfi Coast. You cannot see Umbria in a day. Rome, you cannot see in a month. Cinque Terre you can see in a day, and then you'll want to get out. Florence takes at least 3-4 days, and Venice requires at least five days at an absolute minimum to see.

Otherwise, it is just like doing layovers at an airport. You really don't get to experience anything, you just take some pictures of monuments, but you won't be able to say that you visited any of these places.

The "low key week" at the end of your tour is where the experience is going to be, provided you stay at one place long enough to say that you were actually there long enough to get to know it. To find a decent restaurant, not a place that accommodates 15 tourists with a guide off of a fixed menu, but instead discovering a nice cafe, pastry shop, or restaurant where locals go, is the whole point.

There is no reason to have a car for the places on your list. For the most part, cars are not allowed into the cities in Italy unless you live there, so you'll just collect a bunch of tickets. There is no point in renting a car in Venice, since there are no roads, just waterways and sidewalks.

Stopping in Verona for a few hours doesn't really make much sense, because all you will be able to do is tick it off of a checklist and say, "I've been to Verona," but you really would have never been there, anymore than a layover on an airplane because it takes a few days to see even the basics, or to get to know its food.

For the last week when you will have time to experience Italy, I'd recommend that you figure out where you want to go, and spend that week there. It will be the best week of your trip, rather than packing and going here and there without seeing anything, just taking photos and eating tourist food. In Italy, quantity of places visited is the opposite of quality of the trip.

It's impossible to say whether flying out of Venice or Milan is better, unless we know where you will be. There is no reason to fly out of Milan unless you are going to stay at the Lakes for the last week. Then, it is a convenient airport to fly out of. If you are going to stay in Verona or Venice, then fly out of Venice. Constantly changing location is the best way to ruin a trip to Italy, because you don't get to explore anything more deeply than the tourist veneer and take photos. You come back not even having tasted authentic Italian food, unless you stay some place and do some discovery of the neighborhood you stay at.

Enjoy the tour, but then finding a place to stay and actually visit is in my opinion what you should do.

Here's my suggestion -

Since you're doing the guided tour for the first week, pick the place you like best, and make that your home for the 2nd week where you're low key and on your own. Going to 6 places in one week really doesn't do justice to any of them, but you'll hopefully get an idea of where you liked, so spend that week going back to just that one place that stuck out as special to you. September isn't the height of tourist season in most cities (but IIRC it's big for cruise ships), so you should be able to book while you're there.

I know it sounds appealing right now while planning to spend that 2nd week seeing a bunch more places, but you're going to feel rushed on that tour in some of those stops. Take the second week and return to the place that calls you back!

If you can't decide but want a nice cross-section of activities, Rome is the safest choice. There is so much to see, do and eat there that a week would fly by for just about anyone. Similarly, if you're very focused on art and wine, Florence will be a quick week. And if you like to wander with nothing in particular in mind (or as I call it, the best kind of doing nothing), Venice will make a week feel like nothing, as it is like no other place on earth.

Exactly my sentiment! I can see somebody who has never been there seeking the guidance and shelter of a tour, but that really doesn't immerse you in Italy. It's fine to dip your toe in but that's not much. Two days ago I was with someone who told me they had been to Italy. I asked, "Where?" Their response was, "Everywhere!" They had done a tour, and they didn't see a darn thing. They just got dragged from one place to another where they could take pictures. They'd all eat together, not off the menu, but off of a limited menu that could handle 20 people coming in on a tour at once.

I'm not discrediting tours. Many people could not go to Italy otherwise, without assistance. There are also specifically targeted tours like history, art, even shopping, that are highly curated.

I'm just calling into question the last week, when OP's feet are already wet, wanting to keep squeezing in more and more places. I agree with your suggestion 100%. At some point you have to stop and see and experience a place in Italy.

Turin
 

I recommend you add on a side trip to Turin. It was once a capital = lovely architecture, and has one of the best Egyptian Museums in the world!

Thanks so much for your thoughtful responses. We understand the limitations on the first two weeks of our trip, as we will be in each of the places listed for a few days, and free time built in to the itinerary. Plus we are going a little early to Amalfi. The appeal to us this time was to have tickets, travel, and luggage all taken care of for us since we decided on this trip rather recently. When we return to Italy, we will pick 2-3 of our favorites and spend a week in each one. We have decided to spend the last, relaxing week in the Lakes area and believe it will be the perfect way to end our trip. Thank you again for your suggestions.

Excellent - have fun!