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genoa-tuscany-rome itinerary help needed

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I’m planning a trip to Italy with my husband, and his brother and sister in law for next October 2006 (probably Sep 30-Oct 15). We have 14 full days (not including two travel days) and would like to include Tuscany/Umbria. This will be our second trip to Italy, having visited Rome, Florence and Venice (only for a day each on a cruise) the first time. I’ve tried to add some diversity to our itinerary to meet everyone’s interests (e.g., varying landscape/scenery, small town, big city, access to museums, archeological sites…) - here is our rough itinerary so far:

Day 1: overnight flight from US to Genoa
Day 2: arrive Genoa, train to San Marguerite Liguire or Portovenere (3 nts)
Day 3: day trip to Portofino
Day 4: day trip to Cinque Terra
Day 5: train to Pisa, pick up rental car, visit Pisa, drive to base near Sienna (5 nts)
Day 5-9: visit San G, Volterra, Lucca, Montepuciano, Montalcino, Pienza, ? day
trip to Florence…
Day 10: drive to Assisi (2 nts)
Day 11: visit Deruta, ? Spoleto or Perugia
Day 12: drive from Assisi to Orvieto via Todi, turn in rental car, tour Orvieto, and take
later train to Rome (3 nts)
Day 13-15: visit Rome, ? day trips to Ostia Antica/Hadrian’s villa
Day 16: fly Rome to US

I’ve done some research and have spent time reading advice on this message board, but know I still have a lot more work to do. I greatly appreciate any suggestions from you all to help me improve the itinerary and make it a great trip!

Some questions I have are:
I’m still debating over visiting Cinque Terra/Portofino area – I love the idea of seeing this beautiful area, but one concern I have is that my brother in law had his hip replaced last year - he can get around fine, but I think that extensive or strenuous walking/climbing is out. I’ve read that hiking between towns is a highlight. I’ve also read some pretty mixed reviews about Cinque Terra on this site. Can a visit to Cinque Terra be enjoyed without the hiking between towns, or is there a relatively easy hike that he might be able to do? Is early October a good time to visit? (I originally thought about nixing Cinque Terre, and instead flying into Milan, spending a couple days somewhere (?) in the Lakes area, then heading to Tuscany. But I know that my husband and I will be back to Italy and would prefer to visit Milan and the Lakes and other northern places on another trip. It is still a possibility though.)

I want to avoid frequently changing hotels, and so purposefully didn’t schedule any one nighters. With that said, would there be any benefit to spending one night in Lucca after picking up the car in Pisa, rather than visiting Lucca on a day trip from a base near Sienna. Also, for days 5-10, I’m not sure about staying all 5 nts near Sienna. Is there a benefit to splitting up the stay in Tuscany, for example with 3 nts near Sienna, and 2 nts near Montalcino or Montepulciano? And finally, is day 12 (driving from Assisi, visiting Todi and Orvieto, and then taking a train to Rome) too rushed? It looks to me like it might be. Any suggestions would be greatly appreciated.

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