Please help to plan our best route after landing in Venice

If the logistics of planning seem daunting, it's because you are trying to do it without help. I first suggest that you purchase a good guide. Rick Steves Italy 2019 guide is for sale on this website, or you can purchase it from Amazon.com. In addition, if you haven't already purchased it, I recommend you purchase Europe Through the Backdoor by Rick Steves. This will give you a flavor of the travel mode that many of us find convenient and enjoyable. Once you have an overview, we can help with details.

I just got back from Italy and also flew into / out of Venice. I had been to Italy before, though, so was adding places I hadn't been plus returning to some favorites. I've been to all of the places you mention except Modena.

My first suggestion is not to start in Venice proper. Do it at the end, so you don't have to split your days, and you can be near the airport on your final night. (But no need to stay AT the airport - mainland - unless perhaps you plane out is at the crack of dawn.)

Looks to me you have about 13 nights on the ground (arrive in Italy September 25?).

So you might do this (all by train, no need for a car):

(AVTO express bus from Marco Polo airport to Venice Mestre train station)

Bologna (2 nights)
Modena (1 night)
Parma (2 nights)
Cinque Terre (2 nights)
Florence (3 nights)
Venice (3 nights)

You could do it it in the opposite direction too. Bologna less than two hours by direct train to Venice Mestre train station, and it's an easy 20 min bus ride from there to Marco Polo airport.

Feel free to move nights around. If you aren't big museum people, you could cut a night from Florence and move it to the Cinque Terre. You could do Modena as a day trip from Parma or Bologna.

If you had more time, you could add a stop in Ferrara (between Bologna and Venice), where I visited briefly on my recent trip. It's a really nice town and not very touristy. Of the places you mention, Florence, Venice, and the Cinque Terre will be the most touristy; Bologna, Parma, and (probably) Modena much less so.

Note that Bologna and Parma can both get booked up with trade fares, so check hotel prices early and lock in something in case the towns get booked up - or alter your plans to stay there alternate nights. I use Booking dot com as my primary hotel booking site, though I try to book directly with the property if I can. (Depends on the situation.) You can book stuff now with free cancellation (read the cancellation policy carefully!) if you cancel up to some period before check-in so you could book some hotels right now and revisit them later.

Both Bologna and Parma offer walking tours of the historic city center. The tours (leaving from the Tourist Information office) last 2-2 1/2 hours and cost about 15 Euros. The guides we had in March were very informative AND entertaining!

Thanks for the replies!

Thanks for the idea of not hitting Venice first AND last. Maybe head out from Venice and spend a bit more time at the end. And thanks for checking for booking in and around Bolognia soon. I have heard it is super busy with other foodies. Might look for a tour there to drill down into the good stuff while visiting. Looks easy to get from one city to another, Modena, Parma, Bolognia.

Wondering if I should do Parma and Modena and skip Bolognia all together. Or dropping Cinque Terre for Como. I have been to Florence before but only for 1 1/2 days so way not enough time and have taken a tour and been to the Uffuzi already. Probably can trim a day there. We did find that we were drawn to the small villages over big cities.

If you've been to Florence before, I'd probably skip it, unless you adored it and were sad not to have more time.

I had terrific food in Bologna, but otherwise the big town didn't charm me. I found Parma much more charming for some reason - perhaps because it is smaller.

I love the Italian Riviera. I just got back from my third stay in the Cinque Terre. For me, even though the towns are charming, the big appeal is the hiking between towns. if you are not avid hikers, you might skip it. On the upside, the villages in the CT are smaller than those anywhere else on your itinerary (though during the day, they are mostly pretty mobbed with tourists). I haven't been to Lake Como.