One Day - Lake Como, Lake Garda, Verona, Bologna OR stay an extra day in CT

What time of year will you be travelling in Italy? Which of the five villages of the C.T. will you be staying in?

I would suggest either another night in the Cinque Terre or another night in Venice. Since you've only booked two nights in the Cinque Terre and three in Venice, adding a night in the C.T. would be my choice. That will give you some time to explore all five of the villages or other nearby locations, or take a nice cruise down to Porto Venere and back.

IMHO, you don't have time to visit any of the other locations on your list. It's going to take at least half a day to travel from (for example) from the Cinque Terre to Lago di Como. By the time you get settled in your hotel, you'd only have a few hours to look around and then check out the next morning to head to your next destination. It's going to take half a day+ to travel from the C.T. to Venice, as you're pretty much crossing the whole country. Be sure to allow for adequate travel time between locations.

As this is your first trip to Italy, be sure to do some research on using the trains and other public transit. There are some potentially expensive caveats to be aware of (ie: hefty fines). The details should be in the current Rick Steves Italy guidebook, or post another note here for more details.

I would suggest either another night in the Cinque Terre or another night in Venice

i concur with Ken. Another night in either place would be preferable to adding a one night stay somewhere else

I've used Verona as a one-night stop twice while criss-crossing northern Italy, and have enjoyed it both times. CT to Venice is a hoof, although once you get on the high speed train, just staying on until Venice is nothing. That said, I enjoy Verona. CT to me is a one-and-done place, so I wouldn't extend that part. I haven't been to Venice since 1992, so can't advise your there. Venice can be wonderful, or not. If you're looking for a recess from your trip, consider Verona.

You have such a long set of train rides to go across Venice, plus I am always up for seeing another location. Your endpoints are busy tourist location, so it would be nice to have a change.

If considering Verona, it’s very busy & more expensive during opera season. If opera interests you, wow, definitely experience it! Watching an opera under the stars in the Roman Arena is spectacular. Buy your tickets very soon. They have sent me email ads, so they might be available now. The historical center is very pretty. I like to stay at Hotel Bologna which is very close to the arena on Piazza Bra.

Ferrara is on one of your routes, and it has the castle in the center of the town and some very nice museums. Excellent Emilia-Romagna food without the crowds of Bologna.

I agree you should just stay in Cinque Terre a third night or train to Venice because getting from the CT to Venice is at least a 5-hour slog and the trade off of just spending a single night in a third destination may not really be worth the time it takes.
One-nighters really dissipate once you factor in the time used up getting to your accommodation, checking in, unpacking, packing and checking out the next morning.
If you have an overwhelming desire to see the city center of Verona or Bologna—you could stop over, store your luggage in a train station left luggage locker and walk/tram into the city center for lunch. With Venice in the cards, however, I think your best move is to get there as early as you can so you have 3 full days to enjoy all that’s there.
Have a great trip!

Thanks everyone! Not sure what fines for the trains there are and our thought was breaking up the long train ride as well. I'm not a huge opera person...or even an opera person at all...but I guess when in Italy. :)

I've been wanting to see the lakes with the Alps in the backdrop so I think stopping just to take it in and not have a big agenda for the time as much as considering it a stop on the train route. I personally think the second choice is adding on a day to CT because we are are beach/boat people so that feels like a place I could just take the extra day to chill and enjoy.

You will have to divert from the direct train line to get Alpine views. That will add travel time between the Cinque Terre and Venice. That doesn't mean you shouldn't do it, but there's not going to be a lot of sightseeing time left after you deal with the transportation challenges.

If you add a night in Venice, you can take a day trip to Verona, or Padua, or Vicenza, or whatever in that region.

If you do decide on stopping at Lake Como for a peak, it will be faster to travel to Genoa when leaving the Cinque Terre. You’ll pass Rapallo and Portofino and see another part of the Italian Riviera. Genoa to Milano Centrale is 1:30-1:45 on high-speed trains. Milano Centrale to Varenna-Esino is about :50. Same time to return to Milan and then high-speed trains from Milan to Venezia Santa Lucia take as little as 2:15.
Have a great trip!