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Itinerary help! First time to Italy

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I am planning a trip to Italy with my fiance this year from October 12-24. I have started doing research on which places to see but I'm overwhelmed with all of the possibilities and I would love some direction and help with planning an itinerary, travel logistics, and things to do.

We are 24 and 25, and are not really interested in art or architecture, so churches and museums are not our thing. We're mainly interested in food, wine, shopping (inexpensive, not designer), taking in the scenery, maybe a cooking class, maybe a catacombs tour, etc. We would like to fly into and out of different cities (open jaw) if possible so that we can see Rome and one other city. Which would you recommend: Bologna, Florence, or Venice? Which city would you recommend to fly into or out of?

There are so many places that we would love to see but but the main places are Rome, San Gimignano, possibly Orvieto, possibly Perugia (for the Eurochocolate festival!), and hillside towns in Tuscany. We're thinking about renting a car to get around Tuscany but I'm not sure which town in Tuscany would make the best base to make daytrips out of. I would also love to stay at an agriturismo if possible but I'm not sure we can afford it. Is it possible to find places to stay that are at or under $120 per night? We don't need 4 or 5 star accommodations.

Here are some of the places I have been looking at, although I know that with my limited time there I'll need to pick only a few of these to see: Recommendations?? I may have butchered the spelling of these...

San Gimignano
Siena
Montepulciano
Pienza
Volterra
Todi
Ravenna
Montalcino
Greve
Castilli Romani
Arezzo
Rome
Perugia
Orvieto
Bologna
Florence
Venice

Can anyone recommend an itinerary based off of the details above? Should we rent a car, or would taking the bus/train be better? Affordable places to stay?

Thanks in advance for your help! Any feedback is appreciated.

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