For someone who fell from a bike as a child and ended up with a concussion, a day of biking in the Tuscan hills didn’t immediately grab my attention, but upon the promise of  lunch, wine tasting, frequent stops and good weather, my initial apprehension began to fade and I agreed to go.  The morning of the tour was a warm and cloudless day and, as I applied sun screen for the first time in months, I began to get a little excited.

My friend and I met our guides and seven other participants at the Ponte alle Grazie for our van trip into the Chianti Colli Fiorentini area of Tuscany.  After 30 minutes of careening along dipping roads, we arrive in Montespertoli at an 11th century castle that produces wine, Vin Santo and Laudemio olive oil.  After a quick tour of the factory and a tasting of wine and olive oil as strong as grass, I buy some bottles before we head to the shed housing the bikes. 

At this point I realise I’m supposed to get on a bike now and quickly shuffle through some memories to try to figure out the last time I was actually on one.  All I remember is taking my bike to a shop in Los Angeles to have its tires pumped up, and then I promptly popped it back in the shed and forgot about it.  Nevertheless, I fixed the helmet snugly on my head, swung my leg over the seat and took off up the cypress-lined driveway away from the castle.  A minute later I was horrified to find my legs ached already.  If I was an avid biker, I would have realised that, a) the gear I was in the most difficult one, and b) my seat was too low which added to the difficulty.  For the rest of the trip I subjected my friend to frequent requests for her to yell out her gear number to me so I could attempt to gain some insight into how they worked as well as discover if the trip was really this difficult, or if I was just making it so.

The morning passed quickly and after a while I eased off the brake, relaxed my grip on the handles, and started to look around.  I was surrounded by choppy waves of mountains and a soft, thick haze of what I hoped was early spring, not pollution.  Patterns of olive trees and bare grape vines embellished the hills and wood poles stood straight and proud like a cemetery of crosses.  We pass professional cyclists, easily recognisable by their bright, tight outfits and intensity, and before I start wondering when lunch would be, we stopped for a simple meal of salad, pasta, wine and desert before heading out again.   

It’s a longer stretch this time and from a distance looks flat, but in reality is a slight, steady incline.  Soon I’m at the end of the line of cyclists and, after seeing the person in front of me disappear into the distance, I suddenly realise I’m alone.  I decide not to concern myself with keeping up with the group and potter along at my sloth-like speed for another 20 minutes before I hear a voice behind me ask how I’m doing.  It’s Keith, the Irishman previously leading the group, but who is now at the back, clearly making sure I don’t get lost or tumble into the ditch at the side of the road.  Andy, the Scottish guide in the van following us, must have driven ahead to the front.  Keith and I chatter away until we reach the rest of the group where my friend declares my arrival loudly with; “I had no idea you were so far away!”  Andy was relaxing on the top of the van and I was about to discover the reason for him following us in the van.

We had reached the part of the journey that I will call a mountain, but that Keith and Andy called a hill: a steep, windy 900 meter incline.  Before I could anticipate the pain I was about to endure, Andy pointed to the van and asked, “Who’s coming with me?” And that is when it occurred to me that I was being allowed something very rare in the world of organised tours (and the very thing that usually prevents me from going on them):  I was being given the luxury of choice.  I shot my hand into the air and quickly walked my bike to the van before the expected stampede, but oddly enough, only me, my friend and one other took him up on his offer.  To salvage some dignity, we decided to at least hike.  We arrived at the top of the mountain with yellow flowers in our hair, photos in our cameras, mildly puffing and quite content with our decision, to find the rest of the group red-faced, bathed in sweat, and collapsed on chairs at a nearby café.   Some were even shaking a little.   

At the end of the day we were given lollipops and dropped back at the Ponte alle Grazie.  I walked home with my precious bottles of amber, plum and emerald liquids clinking away in my bag, feeling tired and dazed, but deliciously content, like a kid after a day of playing in the sun.  I had biked 13 miles (23km), been provided with water, food, rest, shelter, companionship and even offered a “push.”  I was taken care of, maybe even coddled a little, and I was so grateful for the help along the way.