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Critique my hill town itinerary in May 2015

Posted by on

Hello,
I am planning to travel from Rome to Florence with my boyfriend, leaving Rome on the morning of Sat May 16 and arriving in Florence sometime on Thurs May 21. We plan to rent a car for part of the time to visit the hill towns. We're thinking of visiting Civita di Banoregio, Orvieto, Pitigliano, Assisi, Val d'Orcia, San Gimignano and Siena during this time. Can you please help critique my rough itinerary?

  • May 16: pick up car from Rome, visit Civita and Orvieto, stay overnight in Orvieto
  • May 17: visit Pitigliano and Assisi, stay in Assisi
  • May 18: visit Val D'Orcia and San Gimignano, stay in San Gimignano
  • May 19: return car to Siena, stay in Siena and take bus/train to Florence on May 21.

Some questions about this initial plan:

  1. Is this is too ambitious - should we cut something out, and if so what?
  2. Is it better to take the train to Orvieto and then pick up a car rental there to avoid driving in Rome?
  3. Should we switch things around to do Pitigliano and Orvieto on the first day, and then San Gimignano and then Assisi on the second?
  4. Should we just return the car in Siena and stay in Siena on May 18 and make a day trip to San Gimignano by public transport the next day?

Any tips about where to park, what else I should be adding in / taking out would be greatly appreciated as well. Many thanks in advance!

Posted by
7737 posts

Personally, I would find your itinerary exhausting. Part of the charm of Italy is slowing down to enjoy it. You've listed seven places to see in four days. However, if you're young and if your goal is just to check off a box for each place, then this itinerary could work for you.

As for your #2, the answer is yes, absolutely yes.

Posted by
11613 posts

I haven't been to a few of the places you mention, but some friends and I rented a car a couple of years ago and visited two towns each day from our bases in Siena and Assisi. I think your plan is doable. I would rather spend time in Todi than in Civita di Bagnoregio, but it's a personal preference.

As to where you pick up the car, perhaps Orvieto would be more convenient than driving out of Roma - you could spend more than 70 minutes driving to Orvieto from Roma if there's traffic, and the train takes only 70 minutes.

Posted by
16893 posts

Assisi is the furthest point from the natural route connecting the others, so I'd cut the half-day in Assisi. Driving times won't necessarily be long; see www.viamichelin.com. But walking in hill towns takes some time, including a lot of going up and down hills, and poking around in corners.

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