The excitement is building as I kick off the new cycling season with the latest tour addition to our Italy lineup: Picture-Perfect Tuscany with Charm. Join me on a ride through Tuscany’s rolling hills, enchanting towns, and hidden local gems — and discover my personal insider tips along the way.
One thing I can say for sure: this tour means much more to me than just the start of a new cycling season. As a former Eurobike tour guide, I was lucky to share countless unforgettable moments with guests in the breathtaking Tuscany. From the very beginning, this region captivated me — it was love at first sight. So, when it came time to choose my Team Member on Tour travel, the decision was clear: I had to return to where it all began. This is my journey back to Tuscany.
Florence, the capital of Tuscany, is the perfect choice as both the start and end point of the tour.
For those like us, arriving by car, I recommend parking at Parcheggio Villa Costanza, a convenient “Drive and Tramway” lot. Easily accessible from the highway, it’s affordable and just a short 20-minute tram ride from the Santa Maria Novella main train station, where our arrival hotel is located.
Our first stroll through the city leads us to Florence’s most iconic landmark, the Duomo Santa Maria del Fiore, with its stunning marble façade. Bathed in the soft evening light, the cathedral feels almost magical and surreal.
After a short train ride to Arezzo, we meet a Eurobike team member and pick up our rental bikes. Thanks to a thorough briefing from our on-site support, we already feel fully prepared.
I highly recommend making a stop in Arezzo. We stroll with our bikes through the charming narrow streets of this beautiful medieval town up to the main square—the heart of Arezzo and one of its most striking sights—the slightly “tilted” Piazza Grande. If you’re lucky enough to visit on the first weekend of the month, you can experience the famous antiques market held there, a well-kept secret cherished by collectors.
Today’s route covers about 60 kilometres. After fuelling up with a cappuccino, we set off on a mostly flat ride through the expansive Chiana Valley. From afar, we spot Cortona—one of Tuscany’s oldest and most beautiful hill towns—perched on the slopes of Monte.
Sant’Egidio. Unfortunately, it begins to rain, and during the final 20 kilometres to Lake Trasimeno, we get thoroughly soaked.
Our accommodation, Hotel Lido, is situated right on the lake. The view from our room’s balcony overlooking Italy’s fourth-largest lake is simply fantastic. For dinner, I recommend sampling the lake’s typical fish varieties, such as carp, perch, eel, tench, and pike.
Once again, we savour the vastness and beauty of Lake Trasimeno as we cycle along an easy-to-ride gravel path right by the water’s edge to Castiglione del Lago. A visit to the old town is highly recommended, especially the Rocca del Leone, which offers a fantastic panoramic view of the lake and the surrounding landscape. Now we leave the lake behind and enter one of Italy’s most varied and stunning regions. Our destination today is Montepulciano. This medieval town, the largest in the Val d’Orcia, sits perched on a hill. We stroll through the old town up to the Piazza Grande and taste the famous Vino Nobile di Montepulciano. Montepulciano is shrouded in mist, giving the town a truly mystical atmosphere — an amazing vibe. With some luck, we snag the last two seats at the very popular Osteria Acquacheta. For meat lovers, the “Bistecca Fiorentina” is an absolute highlight and quite possibly one of the best in town.
We welcome a change of pace and enjoy breakfast at Café Palazzo Avignonesi, surrounded by exquisite 16th-century ceiling frescoes. The array of homemade dolci is simply irresistible—almond cantucci, panforte, torta della nonna, biscotti, and bomboloni. I simply have to try them all!
We roll on through gently undulating hills and a wide-open landscape dotted with the region’s signature cypress-lined lanes. The panoramic route leading up to Pienza rewards us with sweeping views over the valley—no wonder this area was chosen as a backdrop for Hollywood films like Gladiator and The English Patient. The Renaissance town of Pienza is a true gem: compact, full of charm, and easy to explore. All of its main sights are gathered around the central square, including the striking Cathedral of Santa Maria Assunta. In the heart of the square lies Café La Posta. With such a stunning setting, an Aperol is a must—and the spirited Italian owner insists we try one of her specialities: pecorino fritto.
This stage of the route is a highlight in itself, especially with the help of our comprehensive travel documents. We follow the famous Strade Bianche—the iconic white gravel roads— winding through the scenic heart of the Val d’Orcia. It’s one picture-perfect view after another, absolutely breathtaking!
Then comes the challenge of our sporty vacation: the climb up to Montalcino, a picturesque medieval hill town. Our welcoming accommodation sits right beside the imposing Fortezza, which offers magnificent views over the rooftops and the surrounding countryside.
The efforts of yesterday are rewarded today with a long, exhilarating descent from Montalcino down into the valley, before cycling through the rolling hills past Buonconvento and Murlo toward Siena. With almost zero traffic, we ride through the Porta Romana into the old town and suddenly find ourselves in the heart of the stunning Piazza del Campo, dominated by the impressive Torre del Mangia, one of the tallest towers in Italy.
Siena’s cityscape is truly one of a kind, with its historic centre listed as a UNESCO World Heritage site. The city is also a lively university town, famed for the Palio, the thrilling horse race held twice each summer. Another highlight is the cathedral—an architectural marvel famous for its intricate marble floor, crafted from beautifully decorated panels.
For the grand finale of this self-guided cycling tour, we head into Chianti Classico—the region nestled between Florence and Siena, home to some of the finest red wines in the world, internationally loved and highly prized. The softly sweeping hills, enriched with fertile soil and a favourable climate, create the perfect conditions for viticulture.
These final two cycling stages call for some serious pedalling. The route is quite hilly before we return to Florence, but all the more beautiful, offering breathtaking views and charming towns like Radda, Castellina, and Greve.
Not an easy choice—truly one of the most beautiful spots. But which piazza stands out as the most stunning?
For me, it’s undoubtedly Siena: Piazza del Campo is simply one of a kind and ranks among the most beautiful squares in all of Italy. My favourite spot is the cosy, narrow balcony with just a handful of seats at Bar Gelateria La Costarella, offering a breathtaking view over the square and the Torre del Mangia.
