Back in 2005, I went on a cycling tour around Tuscany with Vermont Bicycle Tours. This ended up being one of the best experiences I've ever had, not just on a bike and not just in Italy; I mean best EVER. Now that I've done it, I can highly recommend seeing the area this way if only because it feels like you're in a movie, with the hills and valleys of Tuscany wrapping around you like an IMAX shot. We started in Florence, rode to San Gimignano, Siena, Montelpuciano, Montalcino and Pienza. It was, in a very insufficient word, gorgeous. The mileage wasn't horrible. Now I look back and laugh though. My longest day was 35 miles. On average they were 20-25 mile days for a week.
The Duomo in Siena, which to me, remains the most amazing church I've ever seen, hands down. The striped marble carries through on the inside and is just stunning.
This is me outside the Duomo (cathedral) in Siena.
Even then, I managed to find cat friends wherever I went. This little guy is in Colle Val d'Elsa.
This is the view of San Gimignano from the belltower there. The hills and patchwork fields are amazing. The tower you see is one of the 7 "skyscrapers" that San Gimignano had.
This is the view of San Gimignano from the patio of our villa. You can better see the "skyline" of the town from a distance.
This is near Villa Ducci, near San Gimignano. These were vineyards, which were everywhere we rode, it seemed.
This was the view from my window in the villa in Pienza
This is me near a poppy field somewhere on the way to Pienza.
This is the stereotypical cypress shot that everyone seems to get when they go to Tuscany, but they really are pretty. This was somewhere on the way to Pienza.
This was a house where locals served us lunch on the front porch. I had the best house wine, picci (hand rolled thick pasta, like spaghetti), tomatoes with basil and olive oil and homemade lemon sorbet. It was the lunch of champions! Unfortunately we lost one of our group here, who ended up too drunk to continue riding!
This is me at the town gates of Montepulciano.
This is Montepulciano as seen from a distance. They don't call these "hill towns" for nothing!
This was our picnic stop during one of our day rides. We had a fully stocked SAG wagon as well as guides who really knew how to feed us well!
This is on the way to Montelpulciano, more cypresses.
This was our group out at our last dinner. We survived!
Our group got ready every morning much as you would at home, except the guides would inflate tires and fill water bottles for us. We just had to show up and ride!
Here I am (second in line, in white) finishing off a hill.
Finally, I spent a couple days on my own back in Florence, taking a day trip to Pisa. This is actually much more awe inspiring than I ever imagined!