Is this itinerary crazy?

Yes, it's crazy. What you are proposing is to spend one full day at Lake Como, one full day in Florence, one full day in Rome and a partial day in Milan. The rest of the time you will spend in transport from one place to the next. I know is appears that you will have two days in each place, but when you consider transportation time you will spend as much time in train stations and in transit as you will sightseeing.
You do not have to go to Rome just because someone says you do. With one week you can realistically go to two places. It could be Lake Como and Florence/Tuscany, or Florence/Tuscany and Rome. It would be totally unrealistic to try to go to all those places with 6 nights. Remember you will need to spend your last night in Milan.

Sadly, I have to say it sounds rushed. But if you are both content to just sample a little of the four places, and don't mind spending lots of time traveling and packing, go ahead. Or you can visit the Lake and Rome and save Tuscany for another time. I think you'll enjoy Milan in the short time you'll be there.

Thank you for your insightful replies. I agree and will ask the boyfriend to choose between Lake Como and Rome, and leave the other for a future trip...

-Colette :)

I would definitely not give time to Rome if the romantic countryside is what you want to see. I had been to Italy about 6 times before I went to Rome... I have now been 3 times, but only because other friends wanted to go. I would have been happy with seeing it once...however, I would return to Lake Como, Venice, Tuscany, and the coastal towns in a minute. I would spend half the time in Lake Como and the other half in Tuscany... maybe take a day trip to Florence... otherwise, enjoy the beauty of the countryside, visit some vineyards, hang out in some small villages. Italy is beautiful.

I second Terry Kathryn.

Also, the whole point of Italy is to take it easy and enjoy the simple things. If you are rushing around everywhere you will miss the entire essence of Italy.

Agreed as well.. if you want to do Tuscany and Lake Como - just do that! Rome will be there next time!

I agree Colette that your initial plan was to try to include too many places, too far apart, in too few days, and that your enjoyment of any of the places would suffer. I visited all of the spots you mention last October, in considerably more time, and by far the least favorite of the stops was Milano. If you are really flying out mid-afternoon on Sunday, there is no need to travel to Milano on Saturday and spend the night. From all the other places you list, you can travel to Milano in about three hours on Sunday morning and get to your flight on time. That might mean an early start in Rome, or less early in Florence, but you can enjoy Saturday evening and night in one of those places, and then unwind on a fast and comfortable train in the morning. Enjoy, it should be a wonderful week as long as you don't run yourselves ragged.

Try this: Travel directly to Florence after your arrival in Milan and spend four nights. Do a day trip from Florence to Rome. Work your way back to the Lake for 2 nights. Then 1 night in Milan. BTW - spending your last night at the Lake is doable since you have a mid-afternoon flight but don't underestimate Milan.

I was told on my first trip to Italy that I was crazy for not going to Florence. Didn't do it til trip number three. As much as I enjoyed Rome, you don't have to do anything you don't want. I would stick with Como/Tuscany, or Tuscany/Rome, but we had 5 nights in Rome and we were still rushed (actually, I would do Como/Venice, but that's because I'm a Venice lover).

I see you've made your decision, so what follows is for the benefit of others:

What if I told you that since you're going to be in Europe, you absolutely HAVE to go to Paris? It's amazing. Also, London. You simply HAVE to go to London. It's amazing. And OMG what about Barcelona??!! You just HAVE to go there. You'd (rightly) tell me to take a hike.

That said, I really do love Rome. It's a shame the boyfriend bought the tickets without realizing you could have flown into one city and out another, say, Rome.