We arrived in Florence via the train and stayed in a small little place just down the street from the magnificent Duomo. We had a bit of time to wander around, check out some shops, a few churches and walk down to the river. Florence, while busy, felt much more relaxed then Rome or Venice. We had an early night as the next morning we would set out on our bikes to discover the many hills of the Tuscan countryside.

We rented hybrid bikes in the center of Florence from Florence by Bike. They set up with everything we needed including paneers that we could put all of our stuff in for the next couple nights. Getting out of the city was a bit daunting, but didn’t take long and just an hour later we were already in the hills and amongst the vineyards. Of course that was an uphill climb the whole way and that seemed to be the case for our entire trip until the very end.

We rode through small villages along the winding road as we headed south to our first stop, for lunch, in Greve in Chianti about 3 hours later. A popular small town to stop in with a cute square filled with al fresco restaurants and had what I thought was our first ‘real’ taste of Italian. The food in Italy up until this point was good, but nothing spectacular and our meal here in Greve was fantastic. Carbo-loaded up for the next part of the ride we went up (mostly up) and down the winding countryside and came to a very small town up a extremely steep hill off the main road called  Panzano which had an great view looking down into the valley filled with vineyards.

About 2 hours later we turned off the SR 222 and thinking our hotel was just a few km down the road decided to stop at a winery for a glass or two before we made our final journey. It was a more modern and artsy winery with a delicious chianti merlot mix. We enjoyed the views and relaxing for a while before we got back in the saddle again.

Sadly for us, our hotel was definitely not just around the corner and another 15 km later, up hill we found ourself in Raada in Chianti and praying that our hotel was close! We were relieved when we were told it was just around the corner. It was just approaching 5pm when we arrived to check in. Nick had made the reservation and told them it was my birthday (a day early though) in hopes of an upgrade and well it only kind of worked. There was an upgrade waiting for us, which was great, but it was for the next night and we were only staying at this hotel for one night. Nick had booke the room for the wrong night! Thankfully, they had 1 very small, corner room overlooking the road. So it wasn’t as perfect as it could have been, ie opening the windows of our upgraded suite to the expansive vineyard views below, but it was going to have to do. Our hotel was awesome, traditional tuscan style on the side of a hill with great views and a pool.

The next morning I got up early to lay by the pool before we set sail again, Nick wanted to sleep a bit more, I didn’t mind I was just waiting for a “Happy Birthday” from him! He eventually got down the pool, then we had breakfast, then we went up to sit on the terrace when it finally clicked at about 9:30 that it was my birthday! Okay, so he felt pretty bad and had ran upstairs to get the card (he did have a card already)! Around 11am my birthday ride began and we thankfully the next 4 hour ride seemed to have a few more dowhills. The scenery just seemed to get better and better as we continued all the way to Siena, our next stop.

Siena is beautiful old city that is still surrounded by a wall dating back to medieval times. We stayed a cute hotel just outside the city gates and enjoyed the views on the terrace with some wine before we went out for a birthday dinner. We really liked Siena and had the best meal we’ve had in Italy so far. We were recommended a few places by our hotel and chose this Tavern that was looked like an old wine cellar. We actually got a table considering we didn’t make a reservation and they were full, we told them we’d eat in less than an hour, which for Italian standard is pretty atypical, but was okay for us. Nick had a filet wrapped in filo pastry, which was good, but didn’t compare to my chocolate pasta with a wild boar sauce. Yes, who knew this combination would work, but it did and it was wonderful. They even sang happy birthday and brought us desert while everyone in the small restaurant clapped and sang along. Not a bad birthday at all!

The next morning was our final day of riding. We were told that we MUST go to San Gimgiano then we could easily ride back to Certaldo and catch the train to Florence. Our legs were already tired from 2 days of riding, but we powered on and besides I still hadn’t seen my sunflowers! I really really wanted to see those sunflowers fields that you see in postcards and didn’t think my trip would be complete if I didn’t. Everyone kept saying they are everywhere, but up until this point we still had yet to see a single sunflower, nevermind a entire field of them. Now I had decreased my expectations after some research finding out that we perhaps were a bit late in the season to see the sunflowers in full bloom, but I still had hope.

We left Siena just after breakfast and headed outside of the city back North. About 45 minutes into our ride we were heading down hill and tadah I could seem them in the distance thousands and thousands of sunflowers! I started flying down the hill only to get to the bottom and find that they were all dead, well except for one lone one that had somehow survived. Oh well, at least we saw them.

For the next 2 hours we would pass by field after field after field, of dead sunflowers that is. What a magnificent sight this would be if we came just 2 weeks earlier! We rode through a few small towns surrounded by walls perched up high in the hills and eventually saw signs for San Gimigiano. With only 5 km to go we were getting excited, but realized that this would be the hardest climb yet. 5km straight uphill. We were told at the beginning of the trip by the bike shop that you really earn your views when you cycle Tuscany and boy was she right. This was the hardest climb the whole time, but well worth it at the top. We had lunch in San Gimgiano and took in again the amazing scenery and then it was on to the train station. 

Just outside of San Gimgiano we turned a corner and there they were maybe not thousands, but a couple hundred sunflowers still alive! We were probably up so high that they were still in bloom, super excited! This last part of the ride got even better because for the next 14 km we descended down hill the whole entire way until we got to the train station. We relaxed as we flew down the road taking in the final glimpses of the Tuscan countryside.

We’ll definitely be back someday.