Three Weeks in Italy... Where to go?

This is why God invented guide books. Rick Steves has an excellent book on Italy. Because your question is impossibly broad and depends entirely on your interests, it will be more helpful to you to start with a guidebook then come back here once you have more specific questions. Good luck.

I own all of Rick's books. I have read through all of the Italy books. We are mostly wanting to go to see historical sites and churches. Just wanted to get some opinions on places that other travelers have visited and enjoyed. I have Rick's opinion, but just wanting to see what others deem worthy places of interest.

OK, I'll bite. I've been to Italy a total of 6 times, with the first trip in 1989 and the most recent in 2009. So here are my impressions, in no particular order: I love Rome. I liked Naples once I got used to it (it's stressful, but I do think of going back). I didn't care for my day trip from Naples to Sorrento and Positano (waste of time); if I did this area again, I'd settle in for at least a few days, or skip it. I was underwhelmed by Pompeii, but bowled over by the Archeological Museum in Naples, as well as the amazing sculptures in the Cappella Sansevero. I like Milan more than most do. I didn't love Venice on my first trip (in 1989), but loved it the second time in 2009. Verona was good but not great. Padova is a gem, and has the added bonus of not getting many tourists. I loved relaxing in Varenna (on Lake Como), but didn't like Bellagio at all. I liked Cremona more than Mantova; I also saw Bergamo on that trip, but was jet lagged on that day and don't remember it well. I hated Bologna (I seem to be the only one, and it's the only place in Italy that I have a really strong negative reaction to). I really like Ferrara, Parma, and Ravenna (not quite as taken with Modena, but perhaps seeing someone shoot up in a bathroom there has something to do with this). Turin is another very interesting city, quite different from other Italian ones. I was last in Florence in 1989; I liked it a lot. I also LOVED Lucca, and a late afternoon in Pisa was worthwhile (the souvenir vendors were literally packing up, and the afternoon light was lovely). I didn't like Siena. I enjoyed Spoleto, Spello, Perugia, and Norcia, as well as a walk around the Piano Grande near Castelluccio. You see the problem; everyone who's been to Italy could spit out a list like this, but it may not be helpful to you.

Since you particularly like historical sites and churches, I'd suggest you check the Blue Guide for Italy (or the regions of Italy most of interest). The challenge with the RS guides is that they are very selective, focusing on the subset of places that he has selected as the best experiences (the approach strikes me as teaching someone to visit on their own the highlights that would be on a packaged tour). There's a lot to be said for that, but it is selective. The Blue Guide will give you a detailed description of what's in most towns, focusing on art, architecture, historic sites. That may help you narrow down your choices. Otherwise, as noted in the message above, you'll get everyone's individual lists of favorites, which may not align with your interests.

Sherry's suggestion that you get a Blue Guide is a good one. The other series that gives very detailed information about what's available in the places covered is the Cadogans. There are several volumes for different parts of Italy. I think it's safe to say you'll have no trouble finding interesting churches, but the Cadogan guides have led us to some hardly-known gems. One thought I had, since you want to include Venice, is to devoted a week or so to that area. You could include Padova, Vicenza, Verona, and Ravenna. Lots of history, lots of churches. You could spend the rest of your time in the middle stretch that includes Tuscany, Lazio, and Umbria. Given your stated interest, you really must see Florence and Rome. Orvieto fits in there, and it's easy to get to. I'd suggest Sicily, but it's too far away. Put it on your list for another time.
As your trip shapes up, come back with more questions, but be careful. You may be at the start of an addiction! We 've been to Italy thirteen times and are planning a return in 2014.

I've been to Italy only the one time, and the places I enjoyed most were Stresa, Verona, Venice, and Siena. Florence was nice enough, Pisa and Milan OK, but I did not care much for Rome. I tended to like the smaller places best, rather than the big cities.

I used Sorrento as a base to visit Pompeii, Herculaneum and Naples and fell in love with Sorrento. I enjoyed both archeological sites and also the superb acheological museum in Naples. I also liked Ravenna very much - wonderful Byzantine mosaics. The Cinque Terre should be lovely at that time of year too. I've been to Florence 3 times and liked it better each time. Verona is one of my favorites. Lovely atmosphere and lots to see.

We fell in love with Sorrento too. Our favorite place in Italy. Charming, beautiful, relaxing, fun. Also liked very much: Rome, Assissi, Venice, Montalcino, Montepulciano, Pienza, San Gimignano, Cortona, Positano, Pompeii, Herculaneum, Mt. Vesuvius Not a fan of: Siena, Pisa, Orvieto, Capri, Naples