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Starting to get my head around our first trip to Italy (Emlia Romagna and Le Marche)

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My husband and I would very much like to take our first trip to Italy next year. I like thinking about our trips well in advance, and I've been obsessed about this one for a while. At first, our intent was to go to Rome and Florence, but the more I thought about it and the more I read, the more doubts I started to have. After reading A LOT of trip reports and being particularly fascinated by Jamikins and BikerScott's fabulous adventures in Italy, we both found ourselves drawn to Emilia Romagna (likely with a base in Bologna) and Le Marche (likely with a base in Urbino).

We like the idea of traveling by train to the town surrounding Bologna for sevaral day trips and with stopping at Raveena on the drive to Urbino (recognizing that it's a bit of a detour). My thoughts on what to do in Le Marche are a bit fuzzier at this point, but the slower pace and scenery seem like the area would provide a nice counterpoint. Still, I like the idea of still staying in town rather than at an agroturismo (as nice as some of them sound).

I'm struggling to get my head around the logitstics though, as seemingly straightforward as the trip at this point seems to be. Neither of us has ever rented a car in Europe; we've relied solely on public transport. I understand some of the issues we're going to encounter, especially with respect to parking, but I'm not entirely clear on how to budget our time, e.,g should we sandwich our time in Le Marche between several nights on both ends of our trip in Bologna or should we drive straight from the airport to Le March, jet lag be damned? One other thought I had was to fly into Rome and bus straight from there to Ascoli Piceno for a night/morning before picking up a rental to drive to Urbino. I was having trouble finding car hire information, however, for Ascoli. I'm also a bit worried about car rental because neither of us drives a manual (although I suppose there's time to learn). It sounds as I would be well advised to make my car reservation as well in advance as possible.

We will likely have 10 nights to work with. Our original thought was to travel in early spring (when we were focused on Rome and Florence), but now I'm leaning toward early May or maybe even September. I do know I don't want to go in the summer, as I just don't deal with high heat and humidity very well.

Just a bit more backround. We're in our mid 30s/early 40s and are very active. We love food and drink, people watching, historic sites, architecture and social history. We love art, but if we had to choose between wandering a beautiful town on a pleasant day and an art museum, we'd choose the former 9 times out of 10. It took four trips and a rainy February day before I visited the Louvre, just by way of an example. We don't live in a particularly pedestrian friendly area (Indianapolis) so simply wandering around a lively city or town is fantastic fun for us. We're also avid bikers and hikers and while this trip isn't intended to be active in that regard, a hike in Le Marche or day-long bike tour isn't out of the question either.

So, I guess at this point, I'm just eager to hear any thoughts or ideas on how best to structure the logistics of the trip, or any other suggestions that anybody else. Thanks in advance and thanks to all who have written about their past adventures in Italy. Those reports have provided much inspiration.

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