Thoughts on our Itinerary? (10n/11d - Aosta & Alps, Riviera/CT, Tuscany [incl. Siena & Florence])

You seem very energetic, but are you sure you will be up for a two-hour drive after your flight, and um, also all the rest? I admit I am a slow traveler, but this seems like a lot!
I have done a Milan-Piemonte-Riviera itinerary of similar length, but in different spots so I cannot advise except on hiking and crowds. Yes, you are going to have a problem with CT if you are already acknowledging you are averse to crowds. Camogli offers excellent hiking opportunities without the crowds.
Be sure you have input the drive times into viamichelin, which is more reliable than Google Maps. If you have the stamina, go for it by all means.

This feels pretty packed to me, but I haven't driven in Europe and it may be doable since you'll have a car.

However, I'm very concerned that you plan to fly overnight to Milan, spend time getting out of the airport (it may well take over an hour), deal with a car-rental agency, and then drive for at least two hours (probably sleep-deprived and jetlagged) to Aosta. That seems unsafe to me.

It is fast, but I think you can do it, at least theoretically. Places that concern me:

1. 2-hour drive after an international flight. Hope you sleep on the plane!
2. One night stays: You have three: Siena, Florence, and Milan. Siena seems like a throw-away night. Why not stay the third night in the agriturismo and eliminate one change. (FWIW I would not do one night in Florence, either, especially if art and crowds are not your thing.)

Liguria outside of the CT will have plenty of options for you. Good hiking at Montallegro above Rapallo and less crowded, easy trip by train. Check out the Abbazia Sant'Antonio outside of Montalcino, 12th century, limited hours, lovely.

You'll need to plan another trip to add more destinations.

Hello all! Thanks for the input so far! With the drive that first morning - it sounds dreadful, doesn't it? We originally discussed getting up to Stresa or Lake Como, just for the sake of getting off the plane and getting somewhere that we wanted to see but without a long drive. But then we felt like we'd end up with another one-nighter and we'd rather just muscle through a longer drive but end up where we want to be. We are only doing carry-on bags, so we're hoping we can get to the rental car quickly. We'll also do the paperwork online beforehand to hopefully speed up the pick up. I know it won't be pleasant, but if we each drive an hour, I think we'll be able to handle it. Our hotel in Aosta has a 9am check in, so we're going to head straight for a power nap!

Laurel - great point on the one-nighters. Milan is really just because we needed to be close to the airport but wanted to stay in the city as opposed to an aiport hotel. Siena and Florence had more to do with wanting to be able to start those short days right in the heart of the action. But to your point, I'm going to think about that third night in Montepulciano!

The potential delay at the arrival airport is more about Immigration than getting your luggage, though I suppose if there's no line at Immigration you might have to cool your heels for a bit at baggage claim. At large airports there's a good chance several planes may land at about the same time. If yours is the last one, you may be behind a lot of people at Immigration.

Since you mentioned doing carry on, give thought to when you will do laundry. That is one reason I typically have a four night stay at some point--things are usually line dried in Italy, unless you use a service.

Good point, acraven. I somehow forgot about incoming immigration ( I swear I've done this before, although its been a while!).

What do you all think about Cinque Terre? I mean - we shouldnt' skip it altogether should we? What do you think about the idea to visit in the mornings and evenings? Is there anywhere you can meander to that crowds usually stop before? Oh and, mercifully, there are no cruises docking in La Spezia that weekend :)

There is no doubt Cinque Terre is beautiful. It is an open secret that there are just-as-beautiful alternatives. With a car, I would not even consider it. I hiked four days in Portofino park and say nary another person.

Your itinerary is fine (other than driving after landing) for someone who doesn’t mind crowds. Since you specifically mentioned it, I will give some options. Cinque Terre & Florence are the two that I cringe if Dave is really crowd adverse.

After the Aosta area, consider Torino. There’s beautiful places to see there, food is wonderful, and the crowds are much smaller than Florence. We were there for a couple of days and would like to return.

Lake Como & especially Lake Maggiore will have much less crowds than Cinque Terre, and they are both beautiful.

Bergamo with the Cité Alta section could be a nice location, too.

I’m not trying to talk you out of your itinerary - just sharing thoughts if a friend told me they wanted to enjoy Italy but in less crowded locations.

We had an early morning arrival to Milan MXP and had to wait an hour for the car rental location to open.

The driving after an overnight flight could really be a problem - and not just for you, but for the other people in the accident you may cause. Would you drive drunk? Driving sleep deprived is just as dangerous. Seriously, consider rearranging things a bit. That first day either stay in Milan (there really is quite a lot to see in the city) or take a train to Torino (Turin) which is also a great city with more than enough to do for one day. If you did that then you could rent the car there and be ready to head up to Aosta first thing in the morning. You mention wanting to see the Matterhorn but in your itinerary you do it late in the day. The Matterhorn is notorious for being covered in clouds in the afternoon (they are called banner clouds and develop during the day, even on sunny days). If you went there on your way to Aosta you could see it in the morning, still get to Aosta by mid day. So by doing this you take care of two problems - more likelihood of seeing the Matterhorn and less likelihood of driving impaired.

One of my favorite photos at the Matterhorn - https://andiamo.zenfolio.com/p972905159 (starts at photo # 4) There are also lots of other Aosta area photos in that gallery.

We drove to Monterosso in the Cinque Terre and parked for three nights. It wasn't difficult to do.Our hotel arranged for a taxi to get us from the parking lot.

hello! Thanks to the next round of commenters! :) we are NOT driving into the CT. We will be parking at our hotel in Levanto and then taking trains (noted in itinerary above). While we know we need the car to get between regions and around Tuscany, we'll be minimizing our use of the vehicle whenever possible.

I also appreciate the concern about the morning-after-flight-drive. We are very cautious people and will approach the situation with care - we can take turns or even pull off for a nap. We won't rush! I will look at the train to Turni and picking up car rental there option though- very clever!

Thanks all! would love continued thoughts and ideas, of course! I can't get enough!

Isabel - your photos are amazing! Can you tell me a little more about the spots where you went in Aosta? What time of year were you there? You are clearly a very good photographer too, but the scenery doesn't hurt :)