The Princess & The Pinarello – Italian Travels By Bicycle

This hill sucks. It sucks more than the last one, but less than the ones that will come after: the fifty shades of punishment that only the Tuscan countryside can deliver. I’m slumped in the saddle of my nimble little Pinarello race bike, shoving my feet against the pedals one at a time. At the opportune moment, Andy – blessed, curly-haired, Scot-accented Andy – leans over and whispers, “We’re beating the Canadians!” To which I reply by standing up and cranking on the rest of this hill.

The hills and valleys of Tuscany frame a view of the Castle of Brolio

We’re not racing. This is a vacation, with ultralight bikes, crazy fast roads, and five shots of espresso per day (followed by five glasses of wine per day). But Andy has raced – mostly in the mountain biking circuit – and I feel honored that he’s joined on to Team Beat the Canadians. He’s my coach, my navigator, and my jet pack, putting a hand on my back when I start to gas out and pushing me up the steep slopes. The tour company hosting us want you to feel like a pro racer even if, like me, you’re an amateur just trying to keep up. There’s a sticker on the top tube of my sleek little bike with my name and country flag on it. And on this hill, I’m trying to do the red-white-and-blue proud.

The Canadians are two spunky and tireless folks from Vancouver. Matt is a strong rider (he added a seven kilometer climb to our ride one day “for fun”) and Bobby pedals in his draft all day, the two of them darting around like dragonflies. Also in our little peloton are Steve and Lori from London, though Lori grew up in the States and also lived in Australia for a time; her dialect is a crazy chimera mix of all the places she’s been. Steve is unassuming, quiet on the bike but grinding up every hill like another day at the office (an office with fresh air, vineyards and olive groves, and stone castles from medieval times perched on every hilltop). Lori is training for an Ironman. None of these strongmen wants help up anything, which leaves the support for me. Andy rides next to me when I’ve slid behind and gives me a strategic push to fling me in front of the Canadians.

Cyclists enjoy the open roads and fast descents of the Chianti countryside

We’re here to play, and eat amazing food at hyper-local restaurants in tiny towns that you wouldn’t think to stop at, and drink wine from the vineyards we pass on the road, and soar down the fastest slopes I’ve ever met. We take punishing rides to coffee shops, have espresso, and ride back. Our leader João Correia, who founded our tour company inGamba, knows everyone we meet from the days when he lived in this area training as a pro cyclist. For the first time, I understand the importance and the added joy of connecting with people on my travels. It was always fun to meet people on vacation before, but here in Italy as João told me, your connections give you access to experiences you can’t buy with money. In context, he was referring to some of the really unique things he does, like setting up dinner in the million-dollar wine cellar in the basement of a restaurant in Siena, or showing us around the grounds of Castello di Ama, a castle turned winery and art installation with works from prominent artists from across the world.

The open central piazza of Siena hosts a neighborhood horse race twice a year

But this connection lends itself to simple pleasures too, like watching our B&B proprietress, Anna, describe the frenzied Palio horserace over breakfast in a mix of wild hand gestures and halting English. Or take Raul, the trip’s Portuguese soigner who speaks the language of our sore leg muscles better than the common language of the group, who makes divine little polenta cakes and sweet pasta squares for our rides, and who dresses up in spiffy clothes on the nights that he Skypes with his beautiful wife and daughter back home. Or Luis, the Portuguese mechanic who asks, when presented with a saddle adjustment or a bottle of Limoncello, “one little more?”

It’s these moments that have made this trip amazing. Moments when you feel heroic, moments when you feel crushed, moments when you laugh so hard you can’t breathe. Or pedal so hard you can’t breathe. Or go down a hill so fast it takes your breath away.

On the last day, I draft behind my boyfriend Logan; it’s a little chilly and I’m hiding in the warm windless pocket behind him, conserving my energy because I need practice at it. To each side the hills just lay out, the quiet rows of gnarled grapevines budding with new leaves. Maybe there’s only so much to say about the landscape, the subtleties between forest, grapevines, olive groves, stone towns; they just get repeated over and over. But I will say this: you can’t touch the magic of this landscape in a car. A car pitches around, jittery, cage-like. On a bike the roads smooth out into sinuous curves, and the landscape unfolds one turn at a time. We ride just hard enough to feel it, how effortlessly the bikes do our bidding, how willfully our hearts follow along. I can feel mine pounding in my chest, saying its own goodbyes to Italy.


Emily will be hosting the free presentation “Travelling Off-The-Cuff” at Summit Hut (Speedway location) on Saturday, May 25th at 11am. She will be discussing ways to pack lighter and will share some tips for stress-free trip planning. She will highlight some key accessories to add light packing principles to any trip and explore how to select the right luggage for your trip. You’ll also learn ways to make your trip planning more flexible so that each day is its own adventure!

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