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Best of the Tuscan Towns?

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Hello All,

We're making our fourth trip to Northern Italy and are looking for suggestions on spots in Tuscany or Western Umbria to visit. We have been to these places and will definitely be visiting again on this trip:
1. Florence
2. Peruguia
3. Sienna
4. San Gimanano
(5. Maybe Lucca)
(6. Maybe Cortona)

We'll probably be staying in at Montegufoni Castle in Montespertoli (SW of Florence) just because we've stayed there before and it seems to be pretty central. But we are also open to recommendations on other places to stay in Tuscany. There are two of us - well travelled, 50 and 70 years old.

Any recommendations on any great little Tuscan or Umbrian towns to viist or other sites in the area? Has anyone been to Fiesole? Ravenna? San Marino? Worth a visit?

Thanks All!

Sass

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