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Tuscany Round Trip Self-guided Cycling Tour 8-day (Level 4)
“La vita è bella!” Few places invite you to savor life as beautifully as Tuscany. Rolling hills draped in vineyards, cypress-lined avenues, historic architecture, and cultural treasures accompany you on your cycling journey through this captivating Italian region. In Vinci, you’ll walk in the footsteps of Leonardo da Vinci and in Pisa, you’ll pedal around the iconic leaning tower; and in Florence, you’ll cross the famed Ponte Vecchio. After each day’s ride, delight in world-renowned culinary treats—from antipasti to zabaione. By day, you’ll cycle past endless vineyards; by evening, you’ll have the chance to savor their finest wines. Here, natural splendor meets architectural brilliance—nowhere else in the world does this enchanting combination shine as vividly as it does in Tuscany
Tuscany is a breathtaking region of rolling hills. As you cycle from town to town, you’ll explore its charming countryside along peaceful country roads and scenic paths. The occasional climbs are well worth the effort, offering stunning panoramic views. Please note that traffic can be busier when entering and leaving towns.
If you would like to rent a bike (109 EUR) or E-bike (299 EUR) please email: [email protected]
Slow Tours offers a number of other Cycling Tours in Europe
Arrival in Montecatini Terme
Montecatini Terme is the elegant spa town in Tuscany. Discover the historic town with magnificent thermal baths, well-kept parks, stylish squares, and lively streets. A special highlight is the ride on the historic funicular to charming Montecatini Alto with splendid views.
Montecatini Terme – Pisa approx. 40-90 km
On your way to Lucca, you will pass the small, medieval wine town of Monte Carlo, where one of the few white wines of Tuscany flourishes. (Alternatively, you can take the train to Lucca). A bike ride on the historic city walls offers magnificent views of churches and towers that rise above the countless roofs of the city. Afterwards, you will continue to Lake Massacciuccoli, also called Lake of Giacomo Puccini with stunning views of the sea and Pisa with its Court of Miracles, the “Piazza dei Miracoli” with its Leaning Tower.
Pisa – Casciana Terme approx. 50 km
First, the bike path leads you along the river Arno. Many fertile fields line your way and you will continue your tour through the Pisan hills, on whose gentle slopes sweet wines, olives and juicy peaches grow. You will see small medieval villages located on the hilltops and soon you will have reached today’s destination, the spa town Casciana Terme.
Casciana Terme – San Gimignano approx. 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.
San Gimignano – Siena approx. 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.
Siena – Castellina in Chianti approx. 40 km
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.
Castellina in Chianti – Florenz approx. 65 km
The last day of cycling takes you over a plateau with great views and then hilly to Greve with its enchanting old town centre. The capital of Tuscany draws ever closer and you cycle comfortably on a long descent to the Ponte Vecchio. You are sure to have found your favourite Tuscan wine this week. Treat yourself to it again at the end of your trip in beautiful Florence.
Departure or extension
Tours marked with are special prices.
| Start | End | Max. No. Guests | Accommodation | Price p.p. | ||
|---|---|---|---|---|---|---|
| Oct 10 2026 | Oct 17 2026 | 10 | Single rooms | 1,608€ | ||
| Double rooms | 1,199€ | |||||
| Mar 27 2027 | Apr 03 2027 | 10 | Single rooms | 1,648€ | ||
| Double rooms | 1,239€ | |||||
| Apr 03 2027 | Apr 10 2027 | 10 | Single rooms | 1,648€ | ||
| Double rooms | 1,239€ | |||||
| Apr 10 2027 | Apr 17 2027 | 10 | Single rooms | 1,648€ | ||
| Double rooms | 1,239€ | |||||
| Apr 17 2027 | Apr 24 2027 | 10 | Single rooms | 1,708€ | ||
| Double rooms | 1,299€ | |||||
| Apr 24 2027 | May 01 2027 | 10 | Single rooms | 1,708€ | ||
| Double rooms | 1,299€ | |||||
| May 01 2027 | May 08 2027 | 10 | Single rooms | 1,708€ | ||
| Double rooms | 1,299€ | |||||
| May 08 2027 | May 15 2027 | 10 | Single rooms | 1,708€ | ||
| Double rooms | 1,299€ | |||||
| May 15 2027 | May 22 2027 | 10 | Single rooms | 1,798€ | ||
| Double rooms | 1,389€ | |||||
| May 22 2027 | May 29 2027 | 10 | Single rooms | 1,798€ | ||
| Double rooms | 1,389€ | |||||
| May 29 2027 | Jun 05 2027 | 10 | Single rooms | 1,798€ | ||
| Double rooms | 1,389€ | |||||
| Jun 05 2027 | Jun 12 2027 | 10 | Single rooms | 1,798€ | ||
| Double rooms | 1,389€ | |||||
| Jun 12 2027 | Jun 19 2027 | 10 | Single rooms | 1,798€ | ||
| Double rooms | 1,389€ | |||||
| Jun 19 2027 | Jun 26 2027 | 10 | Single rooms | 1,798€ | ||
| Double rooms | 1,389€ | |||||
| Jun 26 2027 | Jul 03 2027 | 10 | Single rooms | 1,798€ | ||
| Double rooms | 1,389€ | |||||
| Jul 03 2027 | Jul 10 2027 | 10 | Single rooms | 1,798€ | ||
| Double rooms | 1,389€ | |||||
| Jul 10 2027 | Jul 17 2027 | 10 | Single rooms | 1,798€ | ||
| Double rooms | 1,389€ | |||||
| Jul 17 2027 | Jul 24 2027 | 10 | Single rooms | 1,798€ | ||
| Double rooms | 1,389€ | |||||
| Jul 24 2027 | Jul 31 2027 | 10 | Single rooms | 1,798€ | ||
| Double rooms | 1,389€ | |||||
| Jul 31 2027 | Aug 07 2027 | 10 | Single rooms | 1,798€ | ||
| Double rooms | 1,389€ | |||||
| Aug 07 2027 | Aug 14 2027 | 10 | Single rooms | 1,798€ | ||
| Double rooms | 1,389€ | |||||
| Aug 14 2027 | Aug 21 2027 | 10 | Single rooms | 1,798€ | ||
| Double rooms | 1,389€ | |||||
| Aug 21 2027 | Aug 28 2027 | 10 | Single rooms | 1,798€ | ||
| Double rooms | 1,389€ | |||||
| Aug 28 2027 | Sep 04 2027 | 10 | Single rooms | 1,798€ | ||
| Double rooms | 1,389€ | |||||
| Sep 04 2027 | Sep 11 2027 | 10 | Single rooms | 1,708€ | ||
| Double rooms | 1,299€ | |||||
| Sep 11 2027 | Sep 18 2027 | 10 | Single rooms | 1,708€ | ||
| Double rooms | 1,299€ | |||||
| Sep 18 2027 | Sep 25 2027 | 10 | Single rooms | 1,708€ | ||
| Double rooms | 1,299€ | |||||
| Sep 25 2027 | Oct 02 2027 | 10 | Single rooms | 1,648€ | ||
| Double rooms | 1,239€ | |||||
| Oct 02 2027 | Oct 09 2027 | 10 | Single rooms | 1,648€ | ||
| Double rooms | 1,239€ | |||||
| Oct 09 2027 | Oct 16 2027 | 10 | Single rooms | 1,648€ | ||
| Double rooms | 1,239€ |
If you would like to drive yourself before or after your tour, ask us for a quote on any brand new Renault, Peugeot or Citroen vehicle for driving in Europe.
Pick up your vehicle from most capital cities in Europe and return it to your drop off destination. Top insurance cover. Email [email protected] for a competitive quote
Wander the World Without Worry
Local language barriers. Lost passport. Unexpected medical expenses. Sometimes, our trips don’t go as planned. That’s why Slow Tours Pty Ltd wants you to have the most robust travel advisory and protection for your vacation.
Ask us for a quote [email protected]
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