alternatives to Cinque Terre? and other ideas?

"Ciao a tutti" is more correct.
How about including LakeMaggiore and lake Orta in the mix? Very close to Milan Malpensa airport. I like to spend at least couple of night there when I fly from/to Malpensa.

Near the Cinque Terre are also Bonassola or Moneglia. Halfway between Cinque Terre and Portofino or Genoa. You can visit all of the above from there, and you don't have to deal with those obnoxious followers of Rick Steves' cult in Vernazza.

For Tuscany you need to stay in Florence if your boyfriend has never been. You have to think about him too.

It has been a while since I visited but I loved Camogli on the ligurian coast.

I agree with the other writer about basing in Florence. Volterra is another great Tuscan hill town that's worth exploring (and not as overrun as Siena and San Gimigniano). Since you'd mentioned Cinque Terre, specifically Vernazza (which indeed has become overrun by the crush of tourists), are you looking for a few days by the ocean? Why not consider a 3 day trip to one of the Tuscan islands like Elba or Isola del Giglio. I'm partial to Giglio because that's where my mom's family is all from. I've been there over 15 times and is my favorite spot to chill after doing the usual church, museum treks wherever I'm traveling in Italy. The Costa Concordia is finally gone and you can't get a more genuine Italian seaside village and breathtaking ocean views! To get there, train to Orbetello, bus from Orbetello to Porto Santo Stefano, and a 45 minute ferry to Giglio.
In bocca lupo!

After reading the NY Times article on Lerici we went and stayed there a few nites ( http://www.nytimes.com/2010/06/20/travel/20next.html ) Pretty much unknown to American tourists, you'll need to use italian phrases to get by. We had a car, I think it would be harder by public transit. We did a boat trip over to Portovenere, nice to walk around but seemed small for using as a base town. Thought it had much more charm than Portofino, though. Also we visited Santa Margherita and I think that would be my recommendation for you. Right on the train line, bigger town, had a pedestrian-only street the day we visited (not sure if blocked to traffic daily or just 1x a week).

Perugia makes a nice base, even though you've been there. Its a terminal for many regional bus lines, and there is a private train line (really more a streetcar) that we took to Todi. I think it also goes to the vicinity of Deruta. One website with info about lots of the smaller towns is http://penelope.uchicago.edu/Thayer/E/Gazetteer/Places/Europe/Italy/Umbria/_General/accessibility.html

How about Bologna or Ravenna? One of my favorite cities is Ferrara. If it has to be near water, then Lago di Garda might offer some good choices. If your boyfriend hasn't been to these places, it will be new memories for both of you.

Linda,

If you want to visit the Cinque Terre in May, it likely won't be too crowded (but still somewhat busy). I've found that after the crowds clear out in the evenings, the ambience is wonderful. I prefer to stay in Monterosso, which has a much better choice of hotels, restaurants, etc. and my favourite hotel in Europe is located there, as well as some of my favourite restaurants. As Monterosso has both a "new town" and "old town", it seems to "absorb" the crowds much better so it doesn't seem crowded.

If you wanted something nearby, you might also consider staying in Levanto, and while it's "officially" part of the C.T., it's only a four minute rail trip from Monterosso. Levanto also has a beautiful large beach. It's a short walk from the town to the rail station, but that only takes about 10 minutes or so (depending on which part of town you start at).

Porto Venere is not as easily accessible for transportation, so I wouldn't suggest that as a "home base" for that area. Better to go there by boat from Monterosso or one of the other towns for a day trip.