Based on the time you want to spend in and around Perugia you can;t also do both Venice and florence. Your plans give very short shrift to both. Pick one - Venice if you haven;t been there before - and spend more than one day - so you can get at least a little feel for the city.

If you want to give Florence "another shot", you should do it during the off-season. You don't say when this trip is, but if it is between May and the middle of November, expect mobs in Florence -- tourist mobs.

There are more Michaelangelos in Rome than in Florence, and plenty of Renaissance masterworks of painting and architecture.

Take your husband to the National Gallery of Umbrian Art to see great masterpieces and the Accademia in Venice.

Visit Florence some future Thanksgiving -- I'm serious! Or maybe you are not American. Anyway, late November can be pleasant, and you can always hedge your bets by staying in Siena or Arezzo or Lucca or even some of the less famous towns along the train line -- or try Bologna if you like pasta.

Thank you for the input. I guess we'll skip Florence this time around, especially as we're travelling in early June. We have a low tolerance for tourist-y-ness (being New Yorkers, we fancy ourselves above this). We'll instead take some time to enjoy Perugia and Umbria and Venice, and consider a future trip to Florence in the off season. Bologna is definitely on our list for next time too. Thanks again.

Here is another option, which would give you a taste of Florence:

Day 1: train from Rome to Perugia
Day 2: Perugia
Day 3: Perugia
Day 4: in the morning, train from Perugia to Florence (for example: dep 10:01, arr 11:57); check luggage at Deposito Baggagli at the train station; have lunch and afternoon wandering Florence; train to Venice arriving that night (dep 19:00, arr 21:03)
Day 5: Venice
Day 6: Venice
Day 7: fly home

I was thinking about that too - spending just the day in transit in Florence. Something to consider. Thanks.

I think the taste of Florence you will get by waiting in line to stow your luggage and tromping into the center of town to have a lunch in one of Florence's typically not-so-good-touristy restaurants won't be a nice one.

If you opt for this plan, do a lot of research about finding an excellent restaurant without the toruist vibe (very hard to locate in the centro storico) and don't go if the temps have climbed high.

My own view is that is also not easy to find a place to "wander" in the centro storico in Florence once the tourist season starts. Go-with-the-tide would be my description. I fear you will take one look around and want to flee, especially if you have found most corners of Perugia and Umbria to be relatively free of mass tourism and cruise-shippers (and delicious).

I did Florence as a day trip in June several years ago and did not like it. We hit the Accademia and Uffizi and were so overwhelmed by the crowds we headed over to the Oltrarno and then out of town. It was our least fav of the big 3.

Went back 2 years ago in early May and stayed 4 nights. Had a chance to see the Bargello, Santa Croce, San Marco, etc. Much more enjoyable--I would happily return.

Let your husband fall in love with Italy this trip--so you can return for Florence and Bologna.