Northern Italy - Early or Late September? And Itinerary Question?

Dolomites- needs at least one more day.
Do not stay in Verona rather add that night to Lake Como but this still is not enough time.
Since you have already been to Venice skip it this trip and and add those two days, one each, to Lake Como and Dolomites.
These destinations require a lot of driving to get to, so you’d arrive, sleep and leave! Exhausting and not really visiting those places.

I agree with Suki that I would drop one location. I also am concerned if you are coming from North America (?) and plan on driving in the Dolomites right after flying. If you’re thinking Ortesei or similar location, please take the train. You could pick up a car after Cinque Terre - maybe at Lucca. (Be sure you’re knowledgeable about ZTL’s before renting a car.).

I have a feeling this year is going to be very busy in the favorite tourist areas since we’ve all been waiting to travel! Your day trips outside Siena to go explore beyond the top cities may be your favorite experiences.

Just read through your previous itinerary and see you already have been at Siena. Any interest in staying in Arezzo, instead? If so, arrive a few days earlier and attend their Jousting Festival, Sept. 4 - lots of fun the entire day! You would want to fly into Rome, and it’s 2.5 hours by train. Montepulciano, etc. are 50 minutes by car from Arezzo - the same as Siena.

Might be easiest to fly into Rome and out of Milan and skip Venice. And if you’re skipping Venice, give an extra day to the Dolomites and definitely to Lake Como.

Everyone is different, but for me, that's at least two too many destinations. With twelve nights, I would overnight in no more than three places. You will lose more time than you think packing up, traveling to a new place, checking in, unpacking, etc. Since you've already been to Siena, the obvious thing to me would be to drop the Tuscany portion of your trip and concentrate on the North, which will save you a lot of travel & backtracking. However, based on the number of nights you've allocated there, it seems like that's your main interest.

In that case, I would drop Verona, Lake Como, and Cinque Terre and allocate those nights to the Dolomites and Venice. I know a lot of people enjoy Verona, but I've been and it's not somewhere I'm desperate to get back to. I think it's overrated due to the Romeo and Juliet lore, but there are better places in the area to spend time.

Agree with Erin. There is nothing more depressing to me than getting somewhere gorgeous ... and then turning around and leaving the very next day. If you see a lot of 2s and 1s, that is usually a big red flag that the pace if too fast.
When you write out out day by day, add in the travel time, as that gives you a more complete picture of your actual time in a place.
I'm not going to be a hypocrite and pretend I don't drive upon arrival after an overnight flight, but it is planned with a lot of thought and consideration, and 2 hours is our max drive.

Thanks for the replies! I think you’re all right - I was probably trying to fit too much in. So I’m thinking that instead we might fly into Milan and cut Venice and Verona and maybe have an itinerary that looks like this instead:

•Cinque Terre - 3 nights
•Tuscany - 4 nights (or 5 if I can take a day from another spot)
•Dolomites - 3 nights
•Lake Como - 2 nights

Would this be a more reasonable itinerary and allocation of time? And if anyone has advice or an opinion on whether to go early or late September, I would gladly welcome it!

If it gives you an extra day go in early Sept

If you can, I would cut the Cinque Terre and add one night to the other three destinations. Now your pace is 4,3,5. Nice and slow. If the Cinque Terre is a must, cut one night and add it to Lake Como..
I would go early September.

If you cannot go in early September, skip the Dolomites. Too many things close mid to late Sept. of course it depends a bit in exactly where you plan to stay. We were there (Ortisei) later than usual in 2021 and decided we would go in early Sept or skip it in future.

Thanks for the feedback. Early September it is!

I'm so sorry but I have one more question for anyone willing to answer! Would you recommend renting a car for the entire trip (Lake Como, Val Gardena, Tuscany, or Cinque Terre) or just for Tuscany? It looks like for some of the routes it would take an hour or two less than trains or buses.

Early September is best. We had a car for the Dolomites and Tuscany. You don’t need one for Lake Como. I haven’t been to the Cinque Terre so can’t answer that one.

I don't think a car would be helpful at all in the Cinque Terre. It's best to move between the towns by boat or by train.

I've read here on the forum that a car is not the best way to see Lake Como, either. The roads don't usually offer good views of the lake. The lake boats are a better way to get around.

We do not have a car in the Val Gardena, ever. For your itinerary I would only rent a car for Tuscany.

In the Val Gardena, you will receive a bus pass to get you up and down the valley. You’ll need a pass or to buy individual tickets for lifts to get to the higher elevations and the best hikes. If you would like to avoid car rental there and need more advice, please PM me.

Too few days in Lake Como, no need to overnight in Verona. While CT is beautiful, it has lost its charm with me. Consider Turin or Genoa instead. Have fun - we will be in the same general areas but for 5 weeks.

Thank you for the advice! It sounds like definitely no car for Lake Como and Cinque Terre for sure then.