Goethe, too, loved Tuscany, the home of eminent people like Giacomo Puccini and Leonardo da Vinci; Tuscany impresses all of our senses: mouth, nose, ears, and even the stomach. Perhaps with a portion of spaghetti al pesto and a classic Chianti? As a cyclist, you will get many opportunities to perceive the full scale of impressions, colors, shapes, and sounds in this region: the elegance of magnificent castles, the use of forms in the stylish villas, surrounded by the silvery green of the olive groves and the purple of the lilies. Visit Florence, “la bella” – the beautiful one, Siena, Vinci, and Pisa and enjoy the solitude of the wide hills cycling on quiet roads. For centuries, Tuscany has enchanted people. Both the people who have left their traces behind and helped to enrich the culture of this region and the people who came to stay. You will understand once you have been on this trip you will understand why!
Highlights
San Gimignano is known as the city of towers, and in Siena the cityscape is enchanting. Along the Arno, you cycle through peach orchards and olive groves, now and then a view of the sea opens up. Be sure to try the Chianti!
Itinerary
- Day 1: Arrival in Montecatini Terme
- Day 2: Montecatini Terme - Pisa approx. 40-90 km
- Day 3: Pisa – Casciana Terme approx. 50 km
- Day 4: Casciana Terme – San Gimignano approx. 55 km
- Day 5: San Gimignano - Siena approx. 50km
- Day 6: Siena - Castellina in Chianti approx max. 40km
- Day 7: Siena – Florence approx. 50 km + transfer
- 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 Montecatini Terme
In the hotel, you will first get detailed information on the tour and your bikes. Afterwards, we recommend taking a walk in the spa park or taking the historical rack railway train to Montecatini Alto.
Day 2: From Montecatini Terme to Pisa | 40-90 km
The small medieval wine town of Montecarlo—where one of Tuscany’s rare white wines flourishes—lies along the route to Lucca (alternatively, you can reach Montecarlo independently by train). Cycling atop its nearly fully preserved city walls offers an unforgettable experience. The journey then continues to Lake Massacciuccoli, also known as Giacomo Puccini’s lake, boasting breathtaking views all the way to the sea and Pisa’s “Piazza dei
Miracoli,” home to the world-famous Leaning Tower.
Day 3: From Pisa to Casciana Terme | 50km
The cycling route first follows the Arno River, accompanied by fertile fields. Next, you’ll pass through the hills of the Pisa region, where gentle slopes are dotted with sweet vineyards, juicy olives, and ripe peaches. Small medieval villages cling to the hilltops like swallows’ nests. With
these enchanting sights, you’ll soon arrive at today’s destination, the spa town of Casciana Terme.
Day 4: From Casciana Terme to San Gimignano | 55 km
Today, you will cycle on beautiful trails through vineyards and rolling hills to San Gimignano. On your way, you will see images of the original Tuscany as they have been painted many times. Just before you reach today’s destination, the silhouettes of the famous medieval towers appear in front of you. Each aristocratic family once had their own tower here – and these towers still dominate the townscape.
Day 5: From San Gimignano to Siena | 50 km
The beautiful Tuscan landscape on today‘s stage makes you forget the small climbs on the route. Once you reach the small fortified village of Monteriggioni, you will feel as if you were in the Middle Ages. Today’s highlight undoubtedly is the architectonic paradise of Siena.
Day 6: From Sienca to Castellina in Chianti | 40km
Enjoy great views over the vineyards on a beautiful mountain road. Take a break in the stone village of Vagliali and enjoy a good Italian cappuccino before cycling along a
white road through vineyards and deciduous forests to Radda. Fortify yourself for lunch with a typical plate of pasta and savour the atmosphere of this village gem before the tour continues into the heart of Chianti to Castellina.
Day 7: From Siena to Florence | 50 km + bus transfer
The tour takes you into the midst of the wide Chianti region. Only here the world-renowned “Chianti Classico” wine, which is much respected among wine connoisseurs, is grown. The charming wine village of Castellina is on your way to Greve. Thanks to its famous wine and olive production, it is called the capital of the Chianti region. From here you will get back to Florence by public bus (Bike drop-off in Greve).
Day 8: Departure or Extension
Afterwards: individual departure, extension of your trip, or combination with the tours “Venice-Florence” and “Florence-Rome”.
Total Distance: 300-350km (186-218 miles)
- Daily Distance: 40-90km (25-56miles)
- Route information: Tuscany has a wonderful but also hilly landscape. You will cycle on quiet minor roads and sometimes even on country lanes from one famous city to another. Close to bigger cities, traffic is unfortunately unavoidable.
- This tour is available between 28.03. - 10.10.2026
- Starts Saturday
