A Weeklong Bike Trip Through Tuscany

Group travel has always reminded me of those high school trips—buses full of kids headed to Virginia Beach or Orlando, friendships still forming, identities in flux. As an adult, it’s never really called to me. It felt like something for the young who haven’t found their people yet, or old whose people are no longer around for the trip.

I’ve always preferred to travel on my own schedule. To linger. To disappear for an afternoon. To decide, on a whim, that I’ve had enough of a place and move on. So when I joined Butterfield & Robinson on a five-day guided bike and walking trip through Tuscany, I arrived excited to be back in Italy—on a bike, no less—and a little skeptical about the possibilities of group dynamics.

Butterfield & Robinson is coming up on sixty years as a tour company. They started by taking college students on affordable bike trips around Europe, and over time, their scrappy beginnings evolved into a global luxury business operating in more than sixty countries. Traces of that early spirit remain.

Our group was, thankfully, lovely. Still, it wasn’t hard to imagine how a single person could tilt the balance. You cross your fingers and hope that adventure travel self-selects for a certain spirit. We began in Florence. I missed a connecting flight. My luggage was lost. Again. (Italy is now three for three on that front.) Before I’d even arrived, I felt like I was already impacting the group dynamic—the guy who’s late, with no bags. B&R handled it with a calm that felt almost parental: assuring me the driver would meet me whenever I arrived.

When I finally got to our first hotel, the Grand Hotel Minerva, where you wake up and walk out onto Piazza Santa Maria Novella, I was exhausted and out of sorts. I had to do a quick shopping spree for activity-appropriate gear. Italians, it turns out, do not sell shorts out of season. I ended up with a pair of tight, zip-off, spandex-like shorts with lots of extra pockets. I now understand the Euro tourist style I see wandering through San Francisco. I like to think of myself as a stylish person, so I was painfully aware of how off my kit felt. Luckily, I knew of a beautiful small shop in Florence called Tie My Tie, where I picked up a couple of indulgent pieces so I could dress for dinners, along with enough workout clothes to get me through until my bags showed up.

Almost immediately, there was a built-in summer-camp vibe to the culture of the trip—a sense of whimsy in how the guides interacted with the group. There’s a pride in the lengths they go to surprise guests, most clearly seen in the delivery of each trip’s branded T-shirt or cycling jersey—they’ve been hidden in pizza boxes and even dropped from helicopters. This attitude allowed for some truly memorable moments.

Our first dinner was cooked by a private chef and hosted at Officine Gullo House. We gathered in what looked like an extraordinary stove showroom, only to be led—prosecco in hand—through a small door and into a hidden courtyard, then through a garden and into a chapel. Our host, an art historian with a sharp sense of humor, told us we were standing at Botticelli’s tomb. The woman believed to have inspired the Venus de Milo had been buried nearby, having died young, and Botticelli, so taken with her beauty, asked to be laid to rest close to her. Another door opened, another passage, and suddenly we were inside a vast Renaissance church, dark at first, then illuminated all at once. It was overwhelming in the best way. At one point, our guide pulled out his phone to show us a photo of Oprah jokingly “confessing” in an old booth. The absurdity cut through the reverence perfectly.

For a traveler, there are two key touchpoints: the guides, who shape your daily experience, and the trip designer, whose invisible hand creates the moments you remember long after. Our guides were Rachela, born and raised in Tuscany and formidable on many fronts, and Michael, the CEO of the company, who goes on a few trips a year to stay close to the experience. It’s a smart move. Rachela may have drawn the shorter straw with a relatively green partner who also happened to be her boss, but both were engaging and deeply competent.

The real magic came from the trip designer, Courtney—someone who has been with the company for decades. She had started as a guide, learning from the owners, George and Martha Butterfield, and created a career at the company. She’s built on relationships that stretch back to the 1990s. The most meaningful moments were the access those relationships allowed—the things you can only hope to stumble upon on a trip of your own.

That’s how, the following day, I found myself walking from a guided tour of Pienza through the Tuscan hills to a private lunch at Puscina Flowers, a simple and beautiful flower farm tucked into the landscape. We cut flowers before sitting down to an al fresco meal prepared by the farmers, who encouraged us to take flowers back to our rooms. From there, we continued the walk on to our hotel for the evening, naturally scattering along the trail. Evenings drew our small group back together—small bars, long tables, local music, and the ritual of drinks before dinner. 

That night’s hotel proved to be one of the best I’ve experienced. Casa Newton may be my idea of perfection. The original structure dates to 1846 and has been reimagined as a 9-room hotel. My room, called Gervasio but affectionately referred to as “the garage,” was a former outbuilding converted into a spacious bedroom. The palette was soft blues balanced with a mix of vintage and custom furniture that felt like a real aesthetic rather than a corporate take on it. One of the owners, Antonie Bertherat-Kioes, who also led the design of the property, passed through while I was enjoying a Negroni in the rambling grounds and looked as if she had stepped out of a Slim Aarons photograph—a sense of style and presence that made it clear the design was a true work of passion.

The hotel bar was a three-seater with a couple of beautifully designed lounges, and just enough corners for private conversations. As the group trickled in for pre-dinner drinks, the scene felt oddly familiar. One by one, the group gathered, and it struck me that we’d become our own version of The Breakfast Club—a set of outward identities masking more complicated inner lives.

If reduced to type, we were the Wine Expert, the Cheese Writer, the Athlete, the Pop Culture Expert, and whatever I am—the Style Guy.

A trip through Italy is no one’s idea of detention, but there was something similar in the accelerated intimacy. Given enough time together, people move quickly past surface stories. We talked about childhoods, marriages, work, successes, and failures. It became unexpectedly honest.

Part of the appeal of this trip was the promise of biking through Tuscany—one day riding roughly 43 kilometers (26 miles), with about 2,800 feet of elevation gain, from Casa Newton through quaint small towns like Montisi and Trequanda. Being able to bike while traveling has become one of my favorite ways to experience a place. The group would often spread out along the road, a mix of experience levels and a fair number of e-bikes.

The descents on the backroads of Tuscany were, for me, pure heaven. I’m not sure all my new friends shared the same level of enthusiasm, but there was a moment where it felt like we were all kids again—riding toward lunch at Ultima Pietra, a biodynamic winery just outside Castiglion Fiorentino, in the hills of the Val di Chiana.

There were a number of local guides, but Giorgio was my favorite. He’s hard to describe. He gave us a tour of a Franciscan monastery and then his hometown of Cortona. He spoke constantly, with humor and self-awareness, weaving together religion, history, philosophy, Under the Tuscan Sun and a lot of cracks about his ex-wife. He knew how absurd some of it sounded. He made fun of us, gently, in a way very few people can pull off.

That balance—between awe and humor—carried through the week. We moved through Tuscany on foot and by bike; the distances gave us time to get to know each other while also offering moments of solitude. Long walks through rolling hills and grazing sheep loosened conversation. By the end of those days, the physical tiredness felt good, even welcome.

Physically, nothing felt extreme, but there was little downtime. Roadside breaks on walks and rides were stocked with espresso, prosecco, and more snacks than anyone could need. No one was going to bonk.

One fellow traveler and I gravitated toward the cycling. She was well known in a specific corner of endurance sports—easily the athlete of the group—though she thought of herself primarily as a writer. I found her story fascinating, the kind of person I might not have met otherwise. We were the most comfortable on road bikes, so we often rode ahead. Other times, I found myself alone, taking in the countryside: an olive farmer harvesting beside a battered Panda 4×4, the light settling on the vines in a way only Tuscany seems to do. 

At meals, I made a point of sitting next to the wine expert. I’m eager to learn more about wine, and she was fantastically generous with her knowledge. We discovered mutual friends and shared roots in rural upstate New York.

By our final stay at Villa di Piazzano outside Cortona, I was exhausted from the movement, the wine, the food, and the social energy, though not unpleasantly so. The hotel was a perfect ending. The original villa dates to the 15th century, and much of the architecture has been preserved—wood floors and antique furniture sit alongside purposeful updates.

After days of walking and biking, it felt good to lean into that old-world luxury. My room had those oversized windows that actually open (and seem to be outlawed at home), looking out onto the gardens. A large, comfortable bed, high ceilings—falling asleep came easily. On our last night at the hotel bar, I introduced my new friends to the sbagliato and felt like I had made a positive contribution to their lives.

Group travel probably still isn’t my default. But I left Tuscany understanding its power when done well—and with the sense that I’d met a few people I might come to know for a very long time. I think no matter what brought each person to the trip, we left feeling connected.

As Allison Reynolds says in The Breakfast Club: “We’re not wrong… we’re just different.”