Italy Highlights: Bike Ride Through Tuscany

Months in advance of our trip, I had booked a bike ride through Tuscany. I'd found what looked like the perfect tour - scenic, leisurely, casual, and modestly priced. We were scheduled to meet up with our group early on our first morning in Florence. Needless to say, we slept through our alarm. I woke up with that panicked, overslept feeling and asked Alex what time it was. He looked at his watch for a good 30 seconds before he said "this watch makes it look like it's 10." Thinking there might be a chance our van hadn't left on time, Charlie suggested we high-tail it over to the meeting point and try and catch the group. Racing to the bike office in a cab and seeing it locked up and empty was probably the peak of my disappointment.

When we got back to our hotel I immediately emailed Andy and Keith, our hosts, and apologized. I also emailed several other venues to see if we could catch another bike tour. Every outfit in town was booked up (a few pointed out that I was trying to secure space on quite short notice), but at the 11th hour Keith and Andy came through and said we could join the next day's tour.

We met up in Florence and rode in a van to a castle in the Chianti region, about 45 minutes outside the city. Andy gave us a tour of the castle, where a count and countess live and produce wine and olive oil. The day was warm and clear, and there were absolutely gorgeous views from the top of the castle. We climbed back down to a courtyard where Keith was waiting with wine, bread, and olive oil - all so delicious I stockpiled bottles to bring home.

We jumped on bikes and set out, following Keith while Andy trailed behind in a van. The ride was so serene - incredible vistas and frequent stops for water and photo ops. It felt like most of the first hour was downhill. After a while we pulled into a tiny town and stopped for lunch. Andy and Keith were our waiters! They wear many hats. We had a four course meal and chatted with Andy and Keith, who really made the trip for me. They were 2 of the most laid-back and spirited guys I've ever met. By the end of lunch my face hurt from laughing. At one point I asked what time it was and Andy said, "2:30, not that you're very good with time anyway..." Touche, Andy, touche.

After lunch we got back on the road, but only until we came to a massive hill. Keith and Andy warned us what a beast it was - it was steep and went on forever - so a few brave souls rode up it while the rest of us, well, hopped in the van for a lift. We stopped at a cafe for a drink and more conversation, then coasted back to the castle. I was fully prepared to cancel all our other plans in Italy and just go on this ride 6 or 7 more times...but we moved on.