It all began with a late train that caused us to miss our connection back to Lucca. We ended up having to pool our remaining cash and take a taxi. Then, because we returned so late, we decided to sleep in a bit and take a later morning train to Florence, not realizing that there were no connections during the afternoon siesta hours. My original plan to take a cooking class was scrapped too, due to conflicting schedules.
This is how we found ourselves with an open day in Lucca, after our best-laid plans had gone awry. We finally decided to take a train to Montecarlo to go wine tasting, upon the recommendation of the clerk at the apartment we were staying at. A word to the starstruck: Montecarlo, Italy and Monte Carlo, Monaco are two very different places. We were told that once we got to the train station in Montecarlo, that the wineries could be accessed via a short taxi ride. Well, we got off the train and there was nobody around. It was deserted.
We could see a bell tower at the top of a hill in the distance and what looked like a castle, so we decided to walk.
It felt like an adventure. It was quiet, there were no cars around and it was well, really, really, hot. We began to sweat as we walked by olive groves, vineyards and adorable houses-any one of which I could easily live in.
We continued up a narrow, treelined path and finally got to the top. We walked though a stone arch and were instantly transported back in time to a medieveal town.
This is what I was talking about in a earlier post about veering off the beaten path. There were absolutely no tourists, it was quiet and beautiful. We were looking for a winery to go wine tasting, but weren’t having much luck. We wandered by an artisian hard at work.
We walked by an abandoned building, and could hear the buzz of thousands of bees. I could only imagine the honey that was dripping from inside. We decided not to venture in to find out.
We walked by a courtyard that looked out over the valley below. There was also a fortress, built in the 13th century. Finally, after walking around a corner we found this:
They let us in, and we sat outside on the patio, drinking wine and talking, all the while soaking up the beautiful view.
Walking down the hill was much easier in the twilight hours, warm from the wine and cooler from the shade created by the setting sun. On the way back to the train station, we walked by an abandoned mansion for sale and peeked in the windows and wandered around the grounds.

I can only imagine how beautiful this place once was.
I don’t think this would have been nearly as fun if we had a map.
Veering off this beaten path happened again in Siena. We rented a car and drove through absolutely stunning countryside. We never could have seen this from a train. We were driving along S-222, which we found about in our RIck Steves’ guide. We walked around a deserted village, and took some pictures.
We could hear voices from across the road, where the winery was. We walked over, only to find out it was full for the next few hours. Undeterred, we drove down the road till we found a restaurant. There were only a few other people inside, and the food was fantastic. They served this:
Italy’s version of potato chips. Thin slices of French bread drizzled in olive oil.
We happened to drive by this resort, and made a mental note to stay here if we ever find our way back to Italy.
We were in search of an open winery, and finally found one, only to find out it was closed for a wedding. Foiled again, or so it seemed until we drove on down the road. We had once last chance before we got back to Siena. We drove up, and a very nice lady walked to the end of the drive and greeted us. We were thinking she was going to tell us to go away, but she was welcoming us in. We were at Il Castagno, a boutique hotel, restaurant, winery and olive oil mecca. Bonanza. The staff was very accommodating and so very nice. We sat down at a table and ordered wine and appetizers. Our waiter, who spoke English, began to tell us about Tuscan wine.
“It is meant to be enjoyed with friends and family,” he began, “over conversation.” He paused and added in a voice thick with an Italian accent “and with lovers.” He told us that he could not understand why people drink alone, or why they come home from a long day’s work and drink in the kitchen. He said that is when problems start to happen. And to think this beautiful place is only a five minute drive from Siena.
So sometimes when those best laid plans go awry, go with it. Stop. Explore. See. You may just be surprised at what you discover.