The first leg of the hike was from Buonconvento to Montalcino. To preface the post, I should explain that Eliza arranged the trip through a US-based company with local Italian "coordinators" who were available for SOS calls to send you a taxi or whatever if you found yourself hopelessly lost. We weren't following a defined trail, like the AT or whatever. It was much more inventive than that. The company provided us detailed notes explaining each little bit of the walk.
For example: "Soon, you come out into the open at a large umbrella pine. Note on your immediate left the field divided by a hedge. Follow the farm track which you'll find running along the left side of the hedge. You should also see a crenellated castle tower straight ahead and then at 11 o'clock as you follow the farm track. The tower is set within a row of trees which extends considerably further to the right than to the left. You want to make your way to the far right end of the row of trees. While doing so, you pass through a windbreak, then between two fields and eventually, the path curves along a wooded area and hedge on your right."
Two other Americans were taking the same route at the same time. Bill and Barbara live in Salt Lake City and have hiked in many exotic locales, including, for example, Bhutan. We did several of the hikes together and shared some delicious meals.
And after much more walking...the promised land:
And so we reached Montalcino and Eliza got a room with a view: