Exploring Tuscany on Two Wheels: A 6-Day Bike Tour Challenge

Ruth Bergman
Jan 19
7 min read

Updated: Mar 21

Intoduction

"We're biking in Tuscany," Oren said to me in October 2019 as we pulled away from Pienza on the first day of our biking adventure. If you're a biking aficionado and follow pro bike tours, you may share this sentiment. I have always enjoyed biking much more than watching others bike. However, I could certainly get excited about being in Tuscany, which is renowned for its great food, exquisite wine, and some of the most picturesque scenery on the planet. Biking offers several advantages in this setting over driving. The distances are suitable for biking, allowing you to proceed at a leisurely pace and stop at every vineyard for photos. You can indulge in food and drink without guilt, and after a day's ride, the meals taste even better. Wine tasting while riding, however, is not recommended.

Oren selected our tour company, Cicloposse, based on the quality of the bikes they rent. Naturally, we opted for the Challenge Tuscany tour, which covers about 70 km per day and plenty of hills. I was fit, but I wasn’t biking regularly. We decided that we should be able to manage the distance, going slowly if needed. While this is true, we didn’t consider the cumulative strain of biking such distances day after day. Nevertheless, we went for it, and there are no regrets.

The ride is stunning. As you navigate each bend and crest each hill, green vinyards, sown fields, rolling hills, and historic towns reveal themselves. Every meal becomes a memorable experience, offering local dishes crafted with precise attention and delightful flavors.

Day 1: Pienza & Montepulciano

Return to Pienza after an exhilarating 64km journey, pausing in front of Porta al Prato, the main gateway to the charming town.

Pienza, often hailed as a Renaissance jewel, is a picturesque town that I have come to adore, nestled in the heart of Tuscany. Renowned for its stunning architecture and harmonious urban design, Pienza is a UNESCO world heritage site, it was transformed in the 15th century by Pope Pius II, who aimed to create a model Renaissance town. The beautiful Piazza Pio II, dominated by the elegant Cathedral of Pienza and surrounded by charming palazzi is a sight to behold by day or night. The town is also famous for its pecorino cheese, which offers a delightful culinary experience and a strong aroma as you walk the main street. Wandering through the narrow streets and ramparts, the serene atmosphere and breathtaking views of the surrounding Val d'Orcia landscape leave a lasting impression.

In Montepulciano's Piazza Grande, at the historic well, enveloped by the inviting charm of Tuscan architecture.

We rode from Pienza to Monticchiello, a small medieval village. This quiet village boasts narrow streets and ancient walls, providing me with a glimpse into the past. The stunning views from its hilltop location enhance the charm of this quaint town. Meanwhile, Montepulciano, famous for its Vino Nobile wine, offers a blend of Renaissance art and architecture, with its grand palaces and beautiful churches lining the main street. The scent of pizza could not be resisted and we joined other tourists on the steps of the Church of St. Augustine for a rest and some people watching.

Excited for the first day of riding, the ride from Pienza to these enchanting towns is a delightful experience for me, covering approximately 64 kilometers of mild hills that make for an enjoyable cycling adventure. The scenic route showcases the idyllic Tuscan countryside, dotted with vineyards and olive groves, creating a picturesque backdrop for my journey.

Our hotel in Pienza was Il Chiostro, a charming accommodation that offers a blend of comfort and elegance. Previously a convent, Il Chiostro provides a peaceful retreat complete with modern amenities. The view from the terrrace at Il Chiostro is not to be missed, and I recommend a sunset drink or dinner at their gourmet restaurant.

Day 2: Montalcino & Orcia Valley

We set off from Pienza, through the Porta al Cignio, and wound our way down to the valley. I felt the invigorating wind in my hair as I embarked on the day's cycling tour towards Montalcino. The winding road presented a breathtaking panorama of the Orcia Valley, with rolling hills and lush vineyards stretching as far as the eye could see. However, the uphill climb to Montalcino was slow going for me, and I found myself steadily overtaken by various groups of enthusiastic cyclists. Despite the slow going, the beauty of the forest surrounding me made every pedal stroke worthwhile. After a break in Montalcino, we were rewarded with another exhilarating downhill stretch with a rush of adrenaline. For once, I managed to keep pace with Oren, who usually speeds ahead. The descent was thrilling, allowing me to enjoy the breathtaking views while also feeling a sense of accomplishment.

Upon arriving in Montalcino, the charming atmosphere of this ancient hill town welcomed us. Tens of bikes were parked by the fortress, and we explored the town on foot. We took a well-deserved lunch break in the piazza, indulging in delicious pizza and espresso that perfectly complemented the day’s adventures.

With 77 km to ride, I was a bit worried about completing today's ride. We stopped Abbazia di Sant'Antimo to take in the stunning architecture and serene surroundings, but skipped Bagno Vignoni with its ancient thermal baths. We did make it back, and it was by far the longest ride I had done. We took dinner at La Bandita restaurant in Pienza, and enjoyed a steak from local Chianina beef and a deconstructed Tiramisu.

Day 3: Gorgonoza Castle via Trequanda and Lucignano

The weather on this morning was not the best for biking, with a threat of rain. It was, nonetheless, time for us to leave Pienza, and I was really excited about spending the night in a castle. Today's ride took us through rustic landscapes and ancient towns, with charming streets and grand views. On a small gravel section, had an unexpected break when we were stopped by a railroad crossing for fully ten minutes.

Our room is on the left middle arch. very unique setting

At the end of the day we reached the climb to Gorgonza Castle. Our excitement grew as the castle walls and turret came into view. Thankfully, this was a short day with only 45km, and we found time to explore the castle and relax. This accommodation really felt like stepping back in time to a world of knights and aristocracy. Dinner at the castle was included in our tour. We enjoyed delectable pasta with truffles, and finished off the day with Cantucci dipped in local liquor. Heaven!

Day 4: Gorgonzola to Castelina

Today was a pleasant day of cycling, covering 65 km, though with less elevation gain than usual. We have entered the heart of Chianti Classico region, traveling through numerous rolling hills and vineyards. While we didn't taste any wine while biking, we did stop at a winery to sample balsamic vinegar. The vendor introduced us to the idea of pairing balsamic vinegar with cheese and ice cream, but only the well-aged variety.

In Gailole in Chianti, a cycling hub, we discovered L'Eroica, a local bike race where participants use vintage chromoly bikes and wear traditional wool cycling attire. Walking through Radda in Chianti, we stumbled upon an old-time bicycle exhibit, showcasing how bicycles were used by craft people, like a fireman's bike with a length of hose fitted into the bike, or a tailor's bike with a sewing machine, or a photographer packing a camera.

Hotel Palazzo Squarcialupi is the palace for the night. It is the ancient residence of the Squarcialupi family. Our tour organizer rocks the period accommodations. We visited the cellars of Palazzo Squarcialupi for a wine tour and learned about Chianti wines and the strict quality control the wineries practice..

Day 5: Onto San Gimignano

Another 45 kilometers of hills, up and down, brings us to San Gimignano. No amount of prior reading can truly prepare you for the breathtaking beauty and the odd sight of the chimney towers that dominate the landscape. We arrived early and had plenty of time to take in this unique town to view the towers from near and far, from below and from above. We stayed in San Gimignano, so enjoyed some quiet time in the town, which feels like a tourist trap in mid-day when many tourist busses arrive. On the other hand, the view of San Gimignano from the surrounding area is unparalleled in the region.

Day 6: Loop around San Gimignano

We spent our last day in the Tuscan countryside exploring San Gimignano and the surrounding areas. I can't get enough of these local villages nestled in rolling hills, vinyards and olive orchards. 65 kilometers and we're back in San Gimignano and done with our ride.

Final Thoughts

Reflecting on an unforgettable biking journey through Tuscany, I traversed 400 kilometers with an elevation gain of 800 meters, indulging in several kilos of pasta and numerous bottles of wine—who's counting? This adventure was undeniably a bucket list trip, filled with cherished memories of scenic views, culinary delights, and rich cultural experiences.

The trip was aptly named "Challenge Tuscany." It was a challenge for me, but the bigger the challenge, the bigger the sense of accomplishment. By sharing my experience, I hope to inspire others to challenge themselves and consider exploring the beautiful landscapes of Tuscany on two wheels.

From San Gimignano we made our way to Firenze for our return flight. Pictured her the Ponte Veccio. I recommend adding a couple of days in this beautiful city, viewing the architecture and art in every corner, and don't skip Bistecca Florentina.

Cycling Route Maps

Here's some information for those thinking about a bike tour in Tuscany. The tour we took resembles the Challenge Tuscany tour listed on the Cicloposse website, but it's not exactly the same. Juliana from Cicloposse customizes each trip, tailoring it to fit our schedule and preferences.