I'm wondering how you are counting your days. Are your arrival and departure days included in the "two weeks"? also, you have counted Day 10 twice.

I love Verona, though you could visit on your way between Bologna and Venice. If it were me, I would add a day to Bologna since your time there as shown will be taken up with a daytrip to Modena.

Days 1: arr Rome
Day 2: Rome
Day 3: Rome
Day 4: Rome
Days 5: travel to Florence
Day 6: Florence
Day 7: with one daytrip in Tuscany (rent a car); sleep Florence
Day 8: Florence
Day 9: morning train to Bologna
Day 10: daytrip to Modena, sleep Bologna
Days 11: travel to Verona, spend the day, late afternoon train to Venice
Days 12: Venice
Day 13: Venice
Day 14: Venice (is this your departure day? if yes, it doesn't really count)

heeney, make sure that you see Rome & Florence at night, all the sights or lighted. heeney what about Pisa and the Leaning Tower of Pisa. As for Bologna its a college or university city. There are sights to see but lot's of college people when I last visited. Also visiting Tuscany consider Seina or even Cortona (Under the Tuscan Sun)fame. Hey Naples and Positano are great stops also.

Hope this helps

Sorry, I should clarify.
We have 14 total nights in Italy.

Rome - 4
Florence - 4
Bologna - 2
Venice - 3

As you can see, we have 13 planned but an extra day. Not sure where it should go in the existing layout. Or should it be something like:

Rome - 3
Positano - 2
Florence - 4
Bologna - 2
Venice - 3

We have been to Rome/Florence/Venice before. But it was years and years ago and we want to revisit them.

Some people throw Positano into the mix without regard to the logistics and time involved in getting there and then moving on to the next destination. Rome to Positano will take at least a half-day; Positano to Florence a little longer. That's a lot of travel time for what is essentially less than a day and a half. You won't be able to go to Capri or Naples but could stop at Pompeii for a couple of hours on the way to Positano. It's your trip, so you get to decide if that's how you want to allocate your time. Some here would recommend heading to Positano directly upon landing in Rome, but whether that works depends on your arrival time and whether at that point you'd be up for riding 3 trains and a bus (or hiring a driver after the 2nd train arrives in Naples). Could you fly into Naples?

From reading around it sounds like traveling to and from Positano would be a train from rome to Salerno (2.5 hrs), then a ferry to Positano (75mins).
Leaving Positano would be the ferry back to Salerno, then the train to Florence which says is about 3.5 hours.
Figure that's not an issue if we stay 2 nights. But not sure where we'd pull that extra day from in schedule.

The other options we are thinking would be an extra day in Bologna or a night stopover in Verona.

The "out there" option would be to pull a day from somewhere and do two nights in Copenhagen on the way back. We are big foodies and would love to go to Noma as a big end to our anniversary.

Dont forget to factor in the time getting to the train station, waiting for the trains/ferries, then getting to your hotel on the other side - dont just add up the train times and think thats it. Also make sure you have a back-up plan if the ferries arent working.

You could also take the fast train to Naples, the Circumsuviana train to Sorrento then the bus to Positano or hire a driver from Naples or Sorrento.

I have done the trek and I wouldnt do it for two nights.

You need to check the ferry schedule for early May.

Jamikins, thanks for the feedback.
We feel like Amalfi Coast is kind of a must-do but we don't want to spend half out time on trains and buses. Getting your feedback that it isn't work it for two nights is helpful.
What would YOU recommend doing with that extra day?

You are doing enough moving from place to place already. Just add the day to the place that interests you the most. I would pick Rome as there is so much to do and see there.

Glad to help!

I would add it Rome or Bologna. Rome has amazing things to see so you wouldnt run out of time - or you could do a day trip to Tivoli or Orvieto or Ostia Antica from there without the hassle of changing locations.

From Bologna you could do a daytrip to Verona, or Ferrara or Parma...

I would add the 'extra' day to Rome. If you consider that the day you arrive, collect your luggage, go thru customs, transit to the city, check in...that day is pretty much gone.
Your second day is 'jet-lag' day. You might get a late start or need an easy afternoon.
There's sooo much to see and do in Rome. Add the extra day there.

Ok. We may add it to Rome. The only thing keeping us from that is we have been there before as opposed to the Emilia Romagna area.
We'll get to Rome around 9 am and be in the hotel by noon at the latest I expect. We typically hit the ground running too.
We could add it to Bologna but hearing conflicting things in how much time is really needed there.
Also Verona sounds nice. Less for the Romeo Juliet thing as opposed to the old Roman architecture. But seems to make sense less as a day trip from Bologna and more of a night stopover going from Bologna to Venice.

Also, just curious:
Is there "too much" time somewhere? Silly I know.
But, 4 nights in Florence or 3 nights in Venice?
Venice is tiny but something about the fact it's sinking and threatened by rising sea levels makes us want to stay and savor it.

IMO, it's personal preference. I prefer Florence, but there is a huge Team Venice crowd here. Unfortunately, you won't know your preference until you've experienced both. The amount of time you're talking about is only going to scratch the surface.

Four locations seem like plenty for 14 nights...I would lean toward three bases, except that you've said you've already been to the big three. We always like to have some new locations if we are revisiting some. I would either vote for the extra day in Rome or Florence, in both cases to take advantage of another day to day trip. Lots of choices from both locations. If you feel like there are too many "repeat" destinations on this trip, consider deleting one of them and adding somewhere in southern Italy (like Amalfi/Naples/Sicily, etc). The south will be warmer and a little more "exotic" since you have not been there before.