UPDATE: See video to accompany this post here.


Since leaving his corporate job to pursue a creative, entrepreneurial lifestyle, Jeff has been smitten with the prospect of having the freedom to be his own boss, to travel, and to ride motorcycles. This freelance life isn’t as glamorous as that makes it sound. The financial strain, the instability, the pressure, and the late nights are commonplace for us now. In fact as I write this, right now it’s way past 3 a.m., and he’s still hard at work making improvements and additions to our business website, Vagabond Original.

But the good far outweighs those negatives. The day that we traveled through Tuscany on a motorbike was the realization of all those dreams beginning to come to fruition.

The morning started out overcast, gloomy, and with the promise of showers, but we were hopeful that it would soon clear up.

Jeff did a lot of research before we left to plan our route through the Tuscan countryside. The guy who got us set up with the motorbike rental was a kind, slightly-rough looking 40-something. His name was Ricardo. Before we left the rental shop, Jeff asked the guy to take a look at our route and see if he had any recommendations on other good routes we should know about.

Motorcycle guys all have the same look in their eyes when you ask that question. As he drew an alternate plan on our map, he highlighted a long stretch of road and said, “This? This is the Jewel of Tuscany.” With a knowing smile, he described it as only a motorcyclist would. We would be fools to miss it.

We’d head south from Florence, through vineyard country, and down to Siena. Then across the green hills from Asciano to Buonconvento and back again.

Before we headed out of town, we double checked out directions and then set up the GoPro on the bike. Speaking of the bike, meet Sophia.


The day before, Jeff and I were in a shop near the Ponte Vecchio when he said, “This looks like you,” pointing to a curvy brunette on a vintage postcard.

“You think I look like Sophia Loren?

Aren’t I a lucky girl? Anyway, I always help Jeff continue his tradition of naming his motorcycles. I commemorated that self-esteem-boosting moment by naming this bike Sophia.


The ride to Siena was a little rainy, but the sunshine finally broke through and it was a lovely day for a ride.


When we pulled off the main road and headed toward the center of Siena, we were met with an amazing view.


Since it was still early Spring and with the late-ish opening time of the rental shop, we were worried about the early sunset and that we wouldn’t be able to see all that we had planned. We decided just to have lunch in Siena instead of walking all around the beautiful town.


We chose a restaurant close to the nearby basilica where we parked. Jeff got his usual lasagna and I ordered the risotto.


I’d never had risotto before, but I’d seen someone order it earlier in the week and thought it looked like creamy rice, so I decided to give it a try. Unfortunately, mine was made with radicchio (also called Italian chicory), a leafy vegetable that looks very much like a red cabbage. And apparently tastes just like hairspray.

I tried. Really I did. But it was inedible. It was the first time I’ve ever sent anything back to the kitchen – well technically it was Jeff that kindly told the waiter that I wasn’t enjoying it. He as very understanding and accommodating. In a few minutes more, our waiter brought me a plate of spaghetti and bland marinara that I smothered in Parmesan. Even though I left a bit hungry and disappointed in our lunch, I was reminded how grateful I was for the amazing food and deserts we’d had so far on our trip. And even if I had to have Risotto al a Aqua Net, at least I was eating it with this vista in the background.

And imagine if I never ordered the risotto, but went straight for the boring spaghetti. I would have always wondered, and that would have been worse than the taste of the radicchio.


The ride to Asciano was lovely. The landscape was speckled with white blossoms on the trees and we’ve never seen anything in nature so vividly green.

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For miles and miles, we rode through the vibrant green hills dotted with olive and cypress trees. There were villas, vineyards, and farms with sheep grazing the hilly pastures.



We don’t actually have a ton of photographs from this day. That was partly because we wanted to be present in what we were experiencing, not just seeing it all through a viewfinder. Still, we made an effort to balance that with having some valuable video memories to help us share and look back on this adventure. So when we did use the camera, it was mostly for video. Jeff is working on editing the hours and hours of footage, and he assures me he’ll have the video uploaded soon. In the meantime, we took a few screen captures.

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Ricardo wasn’t kidding when he said, “The Jewel of Tuscany.” The views from Asciano to Buonconvento were breathtaking. Jeff and I yelled our praises at each other above the sound of the engine and the wind.

I don’t know if I could ever pick just one place that would top my list as the most beautiful. The volcanic mountains and rain forests in Rwanda, the Alpine Loop in Utah, Victoria Falls in Zambia, the city scapes of Paris, the green hills of Tuscany? I’m glad I don’t have to choose and that I’ve had the great privilege to visit such amazing places around the world.

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One of my favorite things about this route is that the road runs along the top of the hills, not in the valleys or along the rivers. It makes it so you can see huge, sweeping vistas instead of just what’s close around you.

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Just a few hours before sunset, we rounded a corner and caught site of a beautiful abbey across a ravine.


You know when your pictures don’t do any justice to how you actually experienced a moment? This photo would be a good example of that.

Founded in 1313, the Abbey of Monte Oliveto is a large Benedictine monastery with expansive grounds. The chiming bells and red brick buildings nestled in the trees made it one of my favorite stop along our ride.


Another one of my favorite parts of this trip has been collecting small mementos. The idea was inspired by my sister when I asked what she wanted me to bring back for her. She told me that she and her boys collect rocks or pressed leaves to remind them of the time they went on a trip.

I like to document the finding of my mementos for the nephews. This one is Jeff’s favorite.


The ride back to Florence was just as beautiful. We stopped in front of this huge estate. I googled it later. Borgo Beccanella, once a tiny borough outside of Asciano, that has been converted into a destination of lavish apartments and suites. It’s beautiful, but I could do without the €710/night price tag.


Soon the bright blues and greens shifted to golden orange as the sun neared the horizon.

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The setting sun brought back the clouds and a few minutes of cold showers. We were losing light, and the already-cool day was getting downright cold at these speeds. Rather than risk being cold and lost in the dark, we opted to get home faster by looping to the main highway (a painful decision for motorcycle enthusiasts, who have a somehow religious/romantic relationship with country roads).

Even though the scenery wasn’t as charming and our teeth were chattering, we still ended the day with cotton candy colored clouds and caught glimpses of an incredible sunset as the sunbeams burst through the clouds.


In order to beat the rain and the setting sun, we rode a little too long without breaks. We were rather cold and sore when we got back to the hotel. Luckily we got back with just enough time to head down to relax in the warm whirlpool.

A perfect end to a perfect day.




Stay tuned for our next update: Rome by Night

To see more photos:

Wander the Wild on Facebook  |  Jeff’s Instagram  |  Allison’s Instagram