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Two Weeks in Italy: Umbria, Tuscany, Piedmont Itinerary Help

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Hi Board,
First real post here but have been reading replies for quite a while. My wife and I will have two weeks in Italy for our 10th anniversary this May-June. We are relatively seasoned Europe travelers and have both been to Italy multiple times, most recently two weeks in 2008. For our tenth anniversary we are looking primarily to:

- Stay in great hotels (lodging budget $200-$300 per night, less is fine too)
- Eat great food
- Drink Awesome wine
- Relax

We have hit all of the major sites / cities before so outside of a night or two in Rome prior to our flight out I don't anticipate spending much, if any time in major cities like Florence, Siena, Venice, Milan etc.

We are also planning on renting a car. Right now I am trying to get a handle on how much driving we want to do and how many different hotels we want to stay in. The middle part of the trip is really the most challenging and is based around deciding between Piedmont and Emilia Romagna both of which are regions we have never been to. In my mind I am thinking something along the lines of:

Days 1-3: Umbria, stay in Norcia at http://www.palazzoseneca.com
Days 4-6: Tuscany, stay near Montalcino, potentially at: http://www.castellodivelona.it
Days: 7-10: Piedmont or Emilia Romagna, looking at: http://www.hotelcastellodisinio.com
Days: 11-12: Cinque Terre, Vernazza, http://www.lamala.it/en/
Day 13: Rome, Hotel undetermined

What I am really looking for are recommendations on the following:
- Best towns to visit in each of the regions mentioned (Umbria, Tuscany, Piedmont, Emilia-Romagna)

- Your opinion of the pacing of this trip, is this too much driving to still allow for a relaxed pace.

- Hotel recommendations - the above are listed as examples of the type of lodging we would love which is pretty unique for us since this is a special occasion trip. That said I am really open to other options if you have favorites.

- Fun experience based activities that you have personally taken part in and loved - cooking classes, truffle hunting, wine tastings / tours etc.

Any help is greatly appreciated. Will update as we book - grazie!

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