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Travel Planning in Tuscany/Florence

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I'm planning a first time trip to Italy, for my boyfriend and I, for next March. The trip will begin with a couple nights in Venice and end with 4 nights in Rome. I'm undecided about the middle portion of the trip. I originally planned to stay in one of the hill towns of Tuscany, but also considered staying in Florence and taking a couple day trips for wine tasting and sightseeing.

I like the idea of staying in a smaller town and really exploring the local food, wines, and scenery of Tuscany. From what I've read, renting a car seems to be the way to go for that type of stay. I'm curious about the challenges for a first time visitor driving a car in Italy? Should I stick to staying in Florence and taking some guided day tours instead? Would staying on the outskirts of Florence be an option? Seems like public trans might not be as accessible on the outer edges of town..

Any suggestions??

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