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Attention Tuscany/Umbria fans...do the towns start to look alike?...others I should consider & why?

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Doing some early research for our next trip which will include Tuscany and a little of Umbria and trying to determine how long I want to allow for this area. Part of me feels if we see every town mentioned by everyone that they would start to blend together. I believe Maitaitom (senior moment if it was someone else) mentioned in his trip report they saw 20 something towns. Don't they start to look alike?...same architecture, etc.

These are the places on my current list...in your opinion are there others which offer something unique and different to make them worth visiting?

Montepulciano
Pienza
Montalcino
San Gimignano
Orvieto
Assisi
Spello
Possibly Spoleto, Gubbio & Civita

We've been to Siena & Arezzo.

Time in this area isn't an issue - I just need help deciding how much time to allow.

So all you experts...what towns offer something which the above do not?

Thanks for your thoughts and suggestions.

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