Tuscan Trip

First, I suggest counting nights in Italy rather than days (don't count departure day or overnight flight).

It seems easier for most people to fly out of somewhere other than Venezia (international connections can be really early). So, perhaps fly into Venezia, then Verona (you can daytrip to Parma or drop it), then Firenze, Cinque Terre, Lake Como (connect through Milano), and spend your last night in Milano, unless your flight is later in the day. Como is about an hour from Milano, other places on the lake will take longer. If your flight is not early, reverse the route and leave from Venezia.

Trains will get you everywhere you listed, except some places on Lake Como.

Agree with Zoe. A 14 day trip is 12 nights on the ground.

Venice-Verona-Florence-CT- Varenna-Milan.

Look at https://www.rome2rio.com
For estimates on travel times.
If you click on train, go to the bottom and click on map to see which towns you travel thru. Example Verona-Florence passes thru Bologna.

Would you skip Como and do Lake Garda instead ( day trip from Verona)?

New member with similar but different questions. Two week trip to Florence arriving in Venice--mid October leaving from Rome.
Should I post here or get my own topic?

lcolem - start your own thread. When you get replies, you will be notified by e-mail (as long as you've set this up in your forum preferences). Also, it prevents confusion if your questions start to diverge from the OP's.

Apart from Florence, none of the places mentioned are in Tuscany.
A Tuscan Itinerary would be

Florence 3-4 days
Siena 2-3 days
Volterra: 2 days
San Gimignano 1 day
Isle of Elba
Lucca 1 day
Pistoia 1 day
Pisa 1 day

You are right: you are headed for a lot of one day/two night stops, a very rushed trip.

Fly into Venice & out of Milan to save some time. I am going to assume you have 13 nights. Is that right? You do not mention your interests, which could also skew advice. And is this your first trip to Italy? OK, with lots of assumptions and guessing:

Venice - 3 nights is perfect

Verona - What do you want to see here? Personally I am not a fan but many are. Before devoting nights to it, make sure you know what you want to see. OR Leave Venice early, stop here for 5 or 6 hours then continue on to Florence.

Florence - 3 nights for a highlight tour. See a couple of the major museums. Have a plan because advance reservations are advisable for some sites.

Cinque Terre - 3 nights. Assume you like the outdoors and maybe hiking? Boat to PortoVenere is nice, too.

Lago di Como (suggest Varenna) - 3 nights for relaxing, cruising the lake.

OK, you may have one night left with my plan. Obviously Parma has to go. You could spend a night in Verona, or spend your final pre-flight night in Milan. Or add a night to Florence! If you have a late enough flight from Milan you can chance coming in from Lago di Como the morning of departure, but check transit options and travel times carefully.

I agree with Zoe's itinerary. I would take Como over Garda. Traffic into Garda is horrible so I can only imagine how crowded it is.