I should have known better, but when my boyfriend suggested a multi-day bike tour through Tuscany, across the Chianti Hills specifically, I was more focused on visions of myself sipping Chianti than slogging up hills on a bike.
Big mistake.
On day one, only a few hours into our ride, a kind of sob escaped me.
I had turned a corner, my heart filled with the hope that the road was finally going to straighten out, when more uphill revealed itself. Unbeknownst to me at that point, the endless seeming climb was, in fact, pretty endless. It was a 11km (6+ mile) stretch of pure uphill (one of three lengthy climbs), and while it may not have been super steep, the fact that it didn't abate once for 6.83508 miles was exhausting.
When I caught myself making the guttural noise of a wounded bear, a lightbulb went off. My boyfriend had chosen the "hardcore" route without telling me. And since the tour was self-guided, aka just the two of us, I had no one to commiserate with.
We had started the day in Florence, picking up our rented gear at a massive bike shop after a sleepless night in the mosquito and school-trip infested Hotel Donatello in Florence. Mark, a 60-something American expat, met us at the shop to lead us out of the city, with only a quick photo break at the Piazzale Michelangelo, a beautiful square with insane views of Florence (which, unsurprisingly, is at the top of a hill). After biking across fields of olive oil groves, we stopped at a small café in a little town famous for its Terracotta called Impruneta. There, as the piazza's clock tower rang 11am, we embraced the culture, fueling up on espressos and little salami sandwiches.
From here on out, we were on our own, "self-guided" if you will.
We had booked our tour through Bike Tours Direct (at around $800, it was the cheapest bike tour we could find by literally thousands of dollars), who organized our hotels, mapped out an itinerary, and made sure that our luggage was waiting for us at each stop. Mark was only there to outline the route, make sure we got out of the city in one piece, and send us on our way. As he explained the easy, medium and "hardcore" (their description, not mine) options, my eyes glazed over at the many maps, numbers, and stats (plus I was busy with my sandwich), but my boyfriend — a CrossFit-loving, paleo-eating sports and health nut, to paint a picture — was drinking it in.
We parted ways and the adventure began: we had more than 40 miles of road to cover until reaching our hotel (the much nicer and mosquito-less Palazzo San Niccolò) in Radda in Chianti, with a lunch break in Greve. 
As we pedaled towards Greve, I realized my second mistake. We were road biking. Duh, I knew that before of course, but clearly I was having issues recognizing the obvious and understanding the meaning of words. As I was biking along what I would consider a highway, basically floundering through the brush trying to stay as far from the buses and trucks thundering past as possible, I wondered why the term road biking hadn't rung the alarm bells for me that we were, in fact, biking on roads, not through vineyards and fields like I had been fantasizing about.
I was exhausted and miserable, but, a lunch of pizza and spaghetti aglio e olio while overlooking Greve's main square, as dozens of old timer cars inexpicably drove by, made me forget the pain.
Hours later, arriving in Radda,a town on top of a hill, I barely had the energy to take in the beautiful, ancient village (apparently first mentioned in documents in 1002), and how it was enclosed in its original defensive walls. I was sweaty, sore, and covered in about an inch of dust and dirt. But a hot shower and a quick limp to a big bottle of Chianti (obviously) and a plate of homemade spaghetti Carbonara at La Botte di Bacco later (spaghetti twice in one day, I earned it!), I was appeased.
I slept like a rock that night.
The next morning was cloudier than my mood had been during the previous day's uphill slogs. It started raining. I was not happy.
I eyed my bike like the torture device it had felt like yesterday, not sure how my sore calves and butt would be convinced to get back on that thing. Somehow though, they were, and despite a constant pain in my right knee — injured skiing years ago — the day turned out to be amazing.
Unlike the first day, which can only be described as a commute of sorts, today was the bike tour I had imagined: all empty dirt roads, lush green valleys and scenic vineyards. We passed through beautiful, clearly ancient towns like Lecchi, Monti and San Sano, each so small, and so authentic that driving through their tiny, windy streets would have been impossible any other way.
As I stood in San Sano, which was completely, eerily deserted at 2pm, filling up my water bottle from the faucet of a frog shaped fountain, I realized that biking was really the only way to see, and to fully experience, a place like this, hills be damned.
In the wise words of Ernest Hemingway "It is by riding a bicycle that you learn the contours of a country best, since you have to sweat up the hills and coast down them. Thus you remember them as they actually are, while in a motor car only a high hill impresses you, and you have no such accurate remembrance of country you have driven through as you gain by riding a bicycle." He's right. I definitely remember every single hill. But I also remember that frog shaped fountain, and how San Sano might just be one of the most insanely beautiful villages I have ever seen, and how it felt like we had time traveled into the Middle Ages.
I stopped complaining, stopped seeing the cars fly by, and began seeing the beautiful orange poppies growing on the side of the road, the many other cyclists cheerfully yelling ciao! when they whizzed past, realizing how fortunate I was to be able to take a trip like this (and I only briefly forgot again when I could barely move my sore body the next day).
The trip had its ups and downs — metaphorically and physically — but in the end, the ups won out (also metaphorically and physically).
Want to book your own trip?
1. Figure out your budget
Bike tours are surprisingly expensive, so deciding on a budget will narrow down the options a whole lot. We chose Bike Tours Direct because it was the only thing within our budget, and had shorter trips.
2. Decide on a duration
Bike tours are generally a minimum of three days long, but are generally either five or seven. I suggest a longer trip, because this means that you can do fewer miles each day, even take a day off for sightseeing, but still cover more ground. The first and the last day will otherwise mostly feel like a commute.
3. Choose whether to go it alone
Self-guided tours are great if you want the flexibility of seeing what you want when you want. That said, they're not great if you can't follow instructions or read maps or are afraid to make a fool of yourself in a foreign language. Group tours are obviously a great way to meet people, as well as to just shut off and let someone else do the thinking.
4. Pick the terrain/difficulty level
Don't get tricked into a hardcore route like I did. Challenge yourself (it makes the pasta taste better, I swear), but don't overdo it and injure yourself on the first day.
5. Get the right gear
I felt like a bit of an idiot in my full-body spandex, but I can't stress enough how important it is to have the right gear. The padded shorts literally saved my butt, the cushioned gloves kept my hands blister-free, and the spandex, which I sweat through every day, was easily washed in the sink and dry by the next morning. Plus it had an awesome pocket on the lower back from which I could easily access my phone.
SEE ALSO: Here's why I think everyone should bring a selfie stick on vacation
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