We arrived on the bus tired from running all over Florence. Our hotel was easy enough to find and a nice change from the last room we’d been in with windows facing a brick wall. I chose it for it’s included breakfast which meant that I’d be supplied my coffee without going too far or paying too much. With the breakfast came a friendly older woman who smoked in the kitchen with the door shut and served “bacon” for breakfast that was really just hot dogs cut into long thin strips and grilled. This was one of the fancier breakfasts we had in Italy because they also served some sort of Little Debbie type pastry and canned fruit as well. Luckily on day one we went grocery shopping and picked up some fresh fruit and granola bars to get us by.
We had planned to rent bikes in Siena because we’d heard this was prime Tuscan biking land so we headed out on day two to find a place to rent them. (Sean) According to everyone on the internet the best place to rent bikes from was “just outside of town” and had “really great biking route maps, with friendly staff and english versions”. We looked at their website (which on an ipad was no easy task) for directions but were stumped by the information given. After scouring a few different sites I found a few that had the same address associated with the bike shop, so we put in the coordinates in the ol’ google maps and we were off. We walked through Sienna and out the walls on the far side and soon found ourselves on a highway wandering around, occasionally checking the map to make sure the blue dot that was us was still heading in the general right direction. Naomi soon became angry at the thought of us wandering on the side of the highway, which ill admit wasn’t ideal but hey, what were we gonna do. After a brief fit of anger directed half towards me and half towards “this stupid idea, and wandering aimlessly on the side of the highway” I reassured her with the glowing blue dot on my phone that we were headed in the right direction and that we weren’t wandering aimlessly, we were on a mission to rent bicycles so we could tour Tuscany’s countryside. “doesn’t that sound awesome?”.
We kept going and after a couple hours of walking our little blue dot was closing in on the target.
When we arrived at our “Destination” which turned out to be a crappy strip mall, the place was a ghost town. Most of the shops were closed and what do you know, the bike shop doesn’t exist.
(Naomi) Hanger was full blown at this point and lucky for this little strip mall, it had a Conad supermarche. So we bought some beer and a .99 bag of spicy nut, corn nut blend that was, at the time, delicious. Some how we were now at the bottom of a hill that pointed straight up to Siena. I’m sure this was part of their medieval defense strategy, but in my hanger daze it just felt like an Italian prank. I knew that all that stood between me and my beer calories was this hill so I climbed it. Imagining all the good it was doing for my butt muscles on the way up for extra motivation. Once safely back in Siena’s walls we found a lovely little park with a Tuscan view and a bench from which to schwill our cheap Bavarian beers.

The next day was more successful for biking, we actually found a bike shop a few blocks from our hotel on our walk back. They rented us mountain bikes and gave us a map and some directions to another medieval city that was nearby. So we pedaled off on our adventure with two granola bars and some water. We got to the city well enough and it had some cool stuff inside, like a Italian shoemaker who’d had a shop there since what looked like the birth of the city, some little restaurants and a tiny park. From there, were all of the mountain biking trails that we had be sent here to ride. I was at this point starting to get a little hungry and had done what I considered a good amount of riding to earn a little break. (Like I was kinda over it) Sean on the other hand was just getting started, probably getting annoyed by my procrastinating in little Italian shoe shops to avoid the “real” bike riding and antsy to get a move on. So we chose route and took off.
I kept thinking of those pictures I’d seen of people smiling as they pedaled on calm roads through vineyards, drunk on sun and wine. Then would compare that to my own situation as I tried to force my stupid mountain bike uphill in mud over roots and rocks only to fail repeatedly. “Just keep pedaling” Sean would say encouragingly. But unfortunately I think that wine was the only part of this Tuscan adventure I wanted anything to do with anymore. I know that all the muddy, rooty, rocky talk is great for some, but in my defense when we had gone to rent our bikes, I had envisioned touring bikes. At no point was mountain biking or even “off road” mentioned. Then again, I was riding bikes with Sean…

When we picked up the bikes, the guy who rented them to us asked if we knew how to use the shifter in a mixture of sign language and broken english, Naomi said “yes we are good, thank you” and off we went. About two blocks out of the city walls I look back and see Naomi’s legs spinning wildly-out of control fast and the bike going nowhere. As I wait till she catches up I can hear a nice blend of curse words and Karate Kid-esque quotes “stupid bike, stupid-stupid bike”. I look down, the chain is still on so thats a good sign but I see that she managed to shift into the easiest gear. “You know how to use the shifters?” i ask “yes, but how do you make it go back?” Naomi has only ridden a Mtn Bike like twice and is used to her cross/road shifters so I go over it and explain to basically only use her right hand to shift keeping the front derailleur in the middle ring, I pick up the back wheel and peddle with my hands to get the bike to shift so she can see what does what. “Got it?” “Yeah its fine, I just forgot for a second” she replies, I was already a little worried about our “Nice little bike trip”.
Again, this did not fit into my idea of tipsy cruising through sun-dappled vineyards with birds singing in Italian.

(Sean) I think Naomi is glazing over this adventure with selective like memory)
So we make it to the Castle town Monteriggioni which was pretty cool and really small. There are sets of really nice Mtn Bike trails that loop all over the area, using the map we have I picked us out the small route that was recommended for all ability levels. We rode to the trail head which turned out to be a dirt road for about a mile. Naomi had by this point mentioned she was starting to get hungry maybe 2-3 times. “This loop is only like 6 miles and will drop us off back at the castle” i said not wanting to waste more time as getting to this point already took a lot longer than i had thought (i should have known better and i was getting worried). The trails were “well” marked as there were signs from the association that created the network at every intersection but only occasionally a spray painted color mark indicating which loop went where. So basically we knew we were on their trails, just not exactly where. At one point a little boy probably around 7-8 years old was keeping pace with us walking down the trail, I was getting frustrated at our forward movement but really trying to keep positive. We finally managed to figure out the route and came to what appeared (according to the elevation map) to be the biggest climb of the ride. So far we encountered some mud pits, some rocks but nothing too bad, I noticed once or twice Naomi had gotten herself into the wrong gear again and had to stop, change it, explain how it worked again and check if she understood, always with the “yeah i get it, it just wasn’t working”. So before we turn up this hill I say “you should shift into an easier gear before you head up this” “yeah, yeah, fine.” I start riding up the path, it was actually pretty technical with little rock shelves, pockets of mud, roots, loose rocks etc. I try to give a few helpful tips about keeping peddling through and up things and picking lines but when I look back I realize I am talking to myself, Noami was no where to be seen. I turn around a little worried and head back. I find Naomi near the bottom of the hill struggling to mount the bike and peddle it uphill in what appeared to be the hardest gear the bike had (these weren’t the greatest pieces of machinery). The look on her face said it all, and after a few more attempts, a few more slips, a fall, and a leg bashing Naomi marched that bike up the hill spewing hatred for that thing worse than the Westboro Baptist church spews hatred for just about everybody. At the top of the hill I am silent, scared for my life and the bike’s well being. A couple of hikers are coming up from the other direction and I can tell Naomi wants to go and avoid being seen by other human beings. She hops on the bike and just heads down before we have a chance to assess which direction we should head. Naomi’s chosen path actually headed us right back down toward Monteriggioni but effectively cut my “fun easy bike ride through Tuscany hillsides” in half.
We got back to the Castle, had sandwiches and a glass of wine from a lovely little shop before we headed back to Sienna. (dont ask about the ride back to Sienna, you dont want to know)
At the end we were super happy to find out that both the bikes only cost us 10 euro for the whole day, then we ate pizza.

The end.


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