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Five Weeks in Italy

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I am desperately looking for help from all of you Italy experts on our 35 day trip to Italy that I am trying to plan.

This is what we came up with: Any suggestions are welcome!
Sept. 7th arrive in Rome and transfer to Positano
Sept. 7-13th Amalffi Coast...we will be with our friends for 4 nights in a villa in Positano. Would you suggest we stay on Capri for the last 2 nights? We always find it quite nice to enjoy a destination when all the day trippers leave...just a thought. Option 2 is booking a hotel in Positano.

Sept 13th-17 Rome We will book a couple of walking tours.

Sept 17 train to Orvieto. We could spend a night in Orvieto or stay 2 nights at Relais Todi. I am not sure about the distance from Orvieto to Todi. If we stayed 2 nights we could enjoy the pool and also explore Todi.

Sept 19-22 Stop in Deruta on route to Spello, Bevgna, Trevi or Asissi. Scott seemed intriqued by seeing Spelleto and also Gubbio. We think 3 nights staying in one of the towns that is central would be interesting. I am very stumped on where to stay. The more research I do the more confused I get.

We like upscale, but with charm and not stuffy and either in town or a very short drive

Sept. 22-26 stay in Pienza/Montepulcino area. I did email Hotelito Lupaia and they suggested a bike and a hike Company and said they could arrange a cooking class. Any other rec's for that area?

Sept 26-29th Another tough decision. We would like to be in an area to visit Siena and have some time to relax.I thought Castel Banfii looked gorgeous, but we got the feeling that it was more about the wines. La Fontanelle has the appeal of being very close to Sienna. Again any other suggestions?

Sept. 29-Oct. 3rd Lucca.... Alla Corte Degi Angeli looked to have more charm than San Lucca Palace. We put on 4 nights there as we want to spend a day and perhaps a night on the coast.

Oct. 3-6th Florence...JK Palace on AMEX points.

Oct 6-9th Venice

Oct 9th-12 Como We want to do some hiking along with touring.

Oct 12 overnight in Milan if we can go to the Last Supper. If not we can pick up a day elsewhere

Oct 13 Fly home...we still need to check on miles for the 13th.

Thanks for any input! I am especially tearing my hair out on the Umbria and Tuscany segments.
Thanks in advance!!!

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