Gran Fondo Strade Bianche
While Gran Fondo Strade Bianche usually takes place in March, in 2021 it was held in September. This is a true European Gran Fondo—I couldn’t believe how many men were wearing a man-purse at registration! Everyone is fit, and we started out full-gas. Known for its white gravel roads, this ride really tests your skills, in the best of ways. It keeps you engaged, focused, and then you get to the aid stations and you eat a beautiful prosciutto sandwich. But this route saves the best for last. In the closing kilometers, you climb Via Santa Caterina into the old city of Siena before culminating in Piazza del Campo, a stadium of historic, quintessential Italian architecture.
The local touch:
I rode alongside our longtime guide Valentino who grew up mere meters away from the course, on one of the fabled sections of Strade Bianche. It doesn’t get any more local than that.
Dolomites Sella Ronda
While the climbs might be hard, it’s so easy to get to the mind-blowing Dolomites. I landed in Venice at 10 a.m. and by 1:30 p.m. I was on my bike going up the path in San Cassiano toward the Sella Ronda, which takes in four of the iconic passes in the heart of the Dolomites: Passo Campolongo, Passo Pordoi, Passo Sella, and Passo Gardena. I love getting off a plane and starting a ride right away, to get the cobwebs out and to get to a rifugio as fast as possible to take in the massive views, the espresso, and the apple strudel. This is a perfect loop. The whole time I’m thinking, my God, if I lived here and I could do this as my weekly Saturday ride—it would be unbelievable. It’s not fair! To be able to ride the roads steeped in Giro d’Italia history, the Dolomites are one of the sublime cycling playgrounds.
The local touch:
We stayed at Rosa Alpina, a five-star hotel with lovely rooms and a Three-Star Michelin restaurant, all of which makes it an impeccable spot to ride from. Everything about this place is spectacular.
Madonna di Campiglio to Lake Garda (Chef on Wheels)
This 40-kilometer downhill ride is like cycling through a geography lesson. Think beautiful gorges, orchards, and vineyards; there are so many different, amazing landscapes to take in, from mountain scenes out of fairytales to lush foliage near Lake Garda. This led me to where our Dolomites + Lake Garda Chef on Wheels Tour was taking place, which is just a fantastic way to see a region, making culinary memories with Chef Stefano Righetti. It’s a perfect way to take in the food, wine, and scenery of the Italian Alps.
The local touch:
We were guided by three-time Italian Olympic snowboarder Alberto Schiavon, who now rides and guides for DuVine.
Cinque Terre
No one goes to Cinque Terre to ride bikes. But we do. The tourists stick to the pasta joints along the coast, but we venture into rustic, old-world Italy, where there are some of the quietest roads I’ve ridden winding through some of the country’s most magical little towns. With massive vistas of the Mediterranean on one side and quaint, lost villages hidden among terraced vineyards on the other, it’s all you can do to keep from stopping and jumping in for a cool dip.
To top it off, when we reached the village of Riomaggiore, we boarded a private boat to slowly cruise back down along the coast, where we took it all in from the ‘other side.’ And, this time, there was no stopping us from jumping in the crystal waters of the Tyrrhenian Sea.
The local touch:
With the guidance of Isacco, we discovered the secret side of these famous five villages clinging to the Mediterranean coast.
Sonoma Coast / Bodega Bay / Colman Road
Waking up to the haunting sounds of the foghorn on Bodega Bay, and watching the fishing boats roll in and out of the harbor is such a classic California coast vibe. The Sonoma Coast is more rustic than a lot of people realize, and the riding there is spectacular. It’s hilly, but the views make it all worth it: Coleman Valley Road is one of the most amazing roads I’ve ridden on the planet, comparable to routes in Croatia and Mallorca. There’s just nothing but massive views of the blue Pacific, nature all around, including the cows, which gives it a Swiss feel. It’s no wonder they film so many car commercials on this perfect stretch of pavement.
There might not be a place to stop for espresso and strudel like there is in Europe, but what it lacks in that regard it more than makes up for with tranquility and beauty. I couldn’t stop taking photos. Around every single turn it got better—the contrast between the royal blue sky and the emerald green of the grasses was unforgettable.
The local touch:
We know the owners of Terrapin Creek Café well, and they never disappoint with the quality of their food.
Shenandoah Valley, Virginia
I’ve been all around the world, and here’s this little piece of heaven that’s only an hour flight from Boston. Sublime strips of asphalt run beside rough-hewn wooden fences in this pastoral part of Virginia. Horses, vineyards, country roads… take me home!
The highlight is, of course, Skyline Drive through Shenandoah National Park, with its gentle ups and downs through a canopy of hardwood trees. No one here is in a rush—everyone, from cyclists to motorists, is simply enjoying the pristine views. I don’t like to compare places, but there is a little bit of Switzerland in the meadows. It’s such a good place to live well and eat well, that’s not a long ways from home. And don’t forget to try the apple cider donuts!
The local touch:
Our guide Michelle now lives in the Shenandoah Valley after traveling the world for years, and it’s here where she founded a farm-to-table restaurant focused on supporting and highlighting local sustainable food systems.
Vermont
Always quirky in the best of ways, Vermont keeps you on your toes. From the gravel to the beer, the Green Mountain State does things just a little differently from the rest of the world, and this is what makes it so special. You can feel like you’re in the wild and scenic Pyrenees when you’re only a couple hours from the Boston-New York metropolis. And when you see it at the peak of fall foliage, it’s hard to keep your eyes on the road. The best way to learn this eccentric state is to ride across it, stay in the historic and picturesque inns like in Woodstock, swim in its roiling waters in Waitsfield, and take in all the rustic and weird charm of this little corner of New England.
The local touch:
We rode to our chef friend Matt Jennings’ new barn/kitchen in the Champlain Valley for lunch. Matt’s also a cyclist, so he’s such a great fit for us, and he also knew exactly what I wanted to eat.
Bonus: Tuscany with Giacomo
I’ve been riding in the Val d’Orcia forever, and it’s always epic, but this year I was able to do something even more special. Led by our guide Giacomo, who knows everyone and whose family has operated this famous abbey for over 20 years—this is the Abbey in which “The English Patient” was filmed—we stopped for a private lunch, in an unbelievable setting, with the most local of local foods on offer. To be able to eat in a 13th or 14th century abbey around the old oven where the monks used to cook, in the middle of a gorgeous ride, it was like being in the movie!
The local touch:
The fresh-squeezed lemonade from the lemon tree in the courtyard was mixed with Prosecco. Can you say perfect?
