Planning an 8-9 day trip to Italy in late October (due to work); was thinking about Venice + Bologna but worried that weather will be very dreary. Have been to Rome and Tuscany (Florence/Siena/Volterra) so would like to see something different, but don't want to spend whole time in dreary cold rain. We like food, culture, scenery -- would probably want to rent a car. Any suggestions as to itineraries? We would consider a different destination if it seems that Italy is simply too far north for that time of year. Thank you!

Sicily might have better weather.

I agree, Sicily.
http://www.fodors.com/community/euro...rip-report.cfm

We have spent three wonderful trips in Le Marche (east of Tuscany, north of Umbria). Not many tourists, close to the Adriatic and mountains. We stay at LaTavola Marche (google it) but there are many nice agriturismos in the area. La Tavola Marche is excellent. First time we were there was in October weather was fine.

Hope this helps.

Thanks to all of you for the suggestions...for the dates I chose, am coming up with airfares almost $3,000 each from NYC to Catania out of Palermo with 2 stops in and 3 stops home. Not sure I'm in for that -- not relaxing or close to affordable! Is there something I'm missing? Willperson, what's to see in Le Marche (top sites, towns, etc.)?

That sounds funny--there are sevral direct flghts to Rome daily from/to both. Try itasoftware.com
I will try it.
OK---I get $1204 for JFK to Palermo with one connection in Rome---the return is via Zurich and London to JFK
Not ideal, but hardly $3000

One can get a TAP RT NYC-Rome for $889 and an EasyJet RT Rome Palermo for 88€ (all fees included, but not luggage), but a night at the hotel near the Rome airport would have to be added to the total.

Just wanted to thank you all for your advice -- worked out a flight plan and am headed to Sicily for this vacation -- would not have persevered without your kind assistance!

Good---thnaks for reporting.