The tour title says it all. On this cycling tour, you’ll encounter something truly spectacular. The breathtaking landscape unfolds like a painting before you. You’ll pedal past towering cypress avenues, through golden fields of wheat, and along world-famous vineyards. Don’t resist the temptation to sample the exquisite wines produced here. Brunello di Montalcino and Chianti Classico are among Italy’s finest! Culturally, the region is equally rich. While Siena and Florence are world-renowned, you’ll also stay in beautiful medieval towns like Passignano, the sophisticated Montepulciano, charming Montalcino, and picturesque Radda. Let yourself be enchanted by the picture-perfect Tuscany!
Highlights
You'll cycle through a truly dreamlike landscape. Breathtaking views will captivate you as much as the beautiful town centers and culinary delights. Savor the specialties and fine wines in the heart of Italy's wine country!
Itinerary
- Day 1: Arrival in Florence
- Day 2: Florence – Passignano sul Trasimeno approx. 60 km + train ride
- Day 3: Passignano sul Trasimeno – Montepulciano approx. 50 km
- Day 4: Montepulciano – Montalcino approx. 50 km
- Day 5: Montalcino – Siena approx. 55 km
- Day 6: Siena – Radda in Chianti approx. 30/70 km
- Day 7: Radda in Chianti – Florence approx. 55 km
- Day 8: Departure or Extension
All distances are approximate. Due to circumstances beyond control, weather conditions or provisions issued by local authorities, the itinerary may be subject to some changes before and/or during your holiday. For example, along the way you may find temporary deviations/detours caused by roadwork. In this case, please follow the directions posted on site.
Itinerary:
Day 1:Arrival in Florence
Stroll through the charming city and marvel at world-renowned art history.
In the morning, take the train to Arezzo, where a brief stroll through the magnificent old town is a delightful experience. Then, cycle along scenic paths through the Val di Chiana valley. Soon, the charming town of Cortona will come into view, but continue pedaling through olive groves and over gentle hills to Lake Trasimeno. The lakeside bike path will lead you directly to the historic town of Passignano.
Day 3: From Passignano sul Trasimeno to Montepulciano | 50 km
Cycle along the scenic lakeshore to the historic town of Castiglione, where you'll enjoy a stunning view of Lake Trasimeno before leaving Umbria and entering the captivating rolling hills of Tuscany. Glide through the renowned vineyards of Vino Nobile di Montepulciano as you approach the majestic hilltop town of Montepulciano. In the evening, lose yourself in the medieval allure of its winding streets and savor the panoramic vistas of the beautiful countryside.
Day 4: From Montepulciano to Montalcino | 50km
Cycle along a cypress-lined serpentine road towards the charming fortified village of Montechiello. The white gravel roads, or "Strade Bianche," will lead you to the Renaissance town of Pienza, also renowned as a film location for Hollywood's "Gladiator." The picture-perfect landscape of the Val d'Orcia will accompany you on your journey to Montalcino, where one of Italy's most famous red wines, Brunello, is passionately crafted. Be sure to savor this exquisite wine in one of the many local wine bars.
Day 5: From Montalcino to Siena | 55 km
On the renowned routes of the “Eroica” cycle through golden, shimmering wheat fields. The play of colors across the hills is as captivating as the cypress-lined avenues leading to the grand estates of yesteryears. From a distance, you’ll catch sight of the towering Palazzo Pubblico in your destination, Siena. Glide through the famous Piazza del Campo, where the annual Palio horse race is held.
Day 6: From Siena to Radda in Chianti | 30/70 km
Enjoy stunning views over the vineyards from a picturesque mountain road. Pause in the charming stone village of Vagliali for a delightful Italian cappuccino before cycling along a white gravel road through vineyards and deciduous forests to Radda. Refuel with a classic plate of pasta for lunch and soak in the ambiance of this village gem. Wine lovers and cycling enthusiasts should not miss the chance to explore Castellina and the heart of Chianti.
Day 7: From Radda in Chianti to Florence | 55km
Continue on hilly roads towards Florence, winding past grand vineyards, olive groves, and medieval villages until you reach Greve in Chianti. The journey is still accompanied by charming stone houses, cypress avenues, and breathtaking views. As you approach the Tuscan capital, enjoy a long, leisurely descent to the Ponte Vecchio. By now, you’ve likely discovered your favorite Tuscan wine—treat yourself to it one last time as you conclude your journey in beautiful Florence.
Day 8: Departure or Extension
Afterwards: individual departure, extension of your trip, or combination with the tours “Venice-Florence” and “Florence-Rome”.
Total Distance: 300-340km (186-208 miles)
- Daily Distance: 30-55km (15-34miles)
- Route information: Cycling will primarily take place on hilly terrain, with several challenging climbs to tackle starting from the second stage. The route follows low-traffic secondary roads and the so-called Strade Bianche, which are nearly traffic-free, well-maintained gravel roads. However, expect heavier traffic when entering and exiting cities.
- This tour is available between 05.04. - 11.10.2025
- Starts Saturday
