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A week of hiking/walking in Tuscany

Have the book Walking in Tuscany, 43 Walks... and planning an anniversary trip for a fall season (not this year).

We would not be doing super aggressive hikes, so more than a grade 2 (moderately difficult) is out. A 4 hour hike is about max, but a great 5 hour hike would be considered.

Interested in the region east of Florence and not further south than Cortona. Ideas for a base for us? Do not want to be based in Florence. Would prefer a farm or airbnb with walking trails out the back door or easy drive to hikes, good dining, a town or two to explore, low key is good. Would also love recommendations for favorite hikes or abbeys to see.

Best airport and flights (cost too) from West Coast. Any direct flights?

We'd probably take 2 weeks, fly into Rome for 2 days, Florence 2 days, and then spend the rest of the time chilling out in Tuscany, though 2 days at the ocean might be lovely. Open to all ideas.

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