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Tuscany with Charm Self-guided 8-day Cycling Tour Level 4
A plate of pasta paired with a glass of Chianti — a classic scene that could open any film about Italy. On a cycling tour through Tuscany, it’s simply part of everyday life. What truly captivates are the stunning landscapes, charming villages, historic towns, and the carefully chosen accommodations where you’ll stay on our delightful journeys. Your adventure begins in the spa town of Montecatini Terme, from where you’ll pedal through endless vineyards, scenic olive groves, and gently rolling hills. Along the way, you’ll visit world-renowned cities like Florence, Siena, and Pisa. Equally enchanting, though less famous, are the wine village Castellina in Chianti and San Gimignano, the iconic town of towers.
Tuscany is a breathtaking yet hilly region. Good fitness or an e-bike will help you tackle the daily climbs with ease. The stages lead you along charming country roads and quiet paths from one famous town to the next. While you may encounter heavier traffic when entering or leaving towns, much of the route offers peaceful stretches where you can fully immerse yourself in the beauty of Tuscany.
Please book your bike (99 EUR) or E-bike (289 EUR) when you book the tour: [email protected]
Slow Tours offers a number of other Cycling Tours in Europe
Arrival in Montecatini Terme
Tour briefing and bike handover. Take your time to explore the surroundings before you hop in the saddle the next day. A leisurely stroll through the famous spa town is a perfect start—or perhaps a ride on the funicular up to Montecatini Alto?
Montecatini Terme – Pisa approx. 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.
Pisa – Casciana Terme approx. 50 km
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
Casciana Terme – San Gimignano approx. 55 km
You’ll pedal through vineyards and softly rolling hills along picturesque paths toward San Gimignano, surrounded by the timeless beauty of the authentic Tuscan countryside. Just before you arrive, the iconic silhouette of the world-famous medieval towers will come into view. Once owned by noble families, these historic towers still define the town’s charming skyline today.
San Gimignano – Siena approx. 50 km
The stunning Tuscan landscape along today’s route makes the occasional small climb barely noticeable. By the time you reach the fortified village of Monteriggioni, you’ll feel transported back to the Middle Ages. But the undeniable highlight of the day is the architectural gem that is 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. | ||
---|---|---|---|---|---|---|
Mar 28 2026 | Apr 04 2026 | 10 | Single rooms | 2,158€ | ||
Double rooms | 1,579€ | |||||
Apr 04 2026 | Apr 11 2026 | 10 | Single rooms | 2,158€ | ||
Double rooms | 1,579€ | |||||
Apr 11 2026 | Apr 18 2026 | 10 | Single rooms | 2,158€ | ||
Double rooms | 1,579€ | |||||
Apr 18 2026 | Apr 25 2026 | 10 | Single rooms | 2,228€ | ||
Double rooms | 1,649€ | |||||
Apr 25 2026 | May 02 2026 | 10 | Single rooms | 2,228€ | ||
Double rooms | 1,649€ | |||||
May 02 2026 | May 09 2026 | 10 | Single rooms | 2,228€ | ||
Double rooms | 1,649€ | |||||
May 09 2026 | May 16 2026 | 10 | Single rooms | 2,308€ | ||
Double rooms | 1,729€ | |||||
May 16 2026 | May 23 2026 | 10 | Single rooms | 2,308€ | ||
Double rooms | 1,729€ | |||||
May 23 2026 | May 30 2026 | 10 | Single rooms | 2,308€ | ||
Double rooms | 1,729€ | |||||
May 30 2026 | Jun 06 2026 | 10 | Single rooms | 2,308€ | ||
Double rooms | 1,729€ | |||||
Jun 06 2026 | Jun 13 2026 | 10 | Single rooms | 2,308€ | ||
Double rooms | 1,729€ | |||||
Jun 13 2026 | Jun 20 2026 | 10 | Single rooms | 2,308€ | ||
Double rooms | 1,729€ | |||||
Jun 20 2026 | Jun 27 2026 | 10 | Single rooms | 2,308€ | ||
Double rooms | 1,729€ | |||||
Jun 27 2026 | Jul 04 2026 | 10 | Single rooms | 2,308€ | ||
Double rooms | 1,729€ | |||||
Jul 04 2026 | Jul 11 2026 | 10 | Single rooms | 2,308€ | ||
Double rooms | 1,729€ | |||||
Jul 11 2026 | Jul 18 2026 | 10 | Single rooms | 2,308€ | ||
Double rooms | 1,729€ | |||||
Jul 18 2026 | Jul 25 2026 | 10 | Single rooms | 2,308€ | ||
Double rooms | 1,729€ | |||||
Jul 25 2026 | Aug 01 2026 | 10 | Single rooms | 2,308€ | ||
Double rooms | 1,729€ | |||||
Aug 01 2026 | Aug 08 2026 | 10 | Single rooms | 2,308€ | ||
Double rooms | 1,729€ | |||||
Aug 08 2026 | Aug 15 2026 | 10 | Single rooms | 2,308€ | ||
Double rooms | 1,729€ | |||||
Aug 15 2026 | Aug 22 2026 | 10 | Single rooms | 2,308€ | ||
Double rooms | 1,729€ | |||||
Aug 22 2026 | Aug 29 2026 | 10 | Single rooms | 2,308€ | ||
Double rooms | 1,729€ | |||||
Aug 29 2026 | Sep 05 2026 | 10 | Single rooms | 2,308€ | ||
Double rooms | 1,729€ | |||||
Sep 05 2026 | Sep 12 2026 | 10 | Single rooms | 2,228€ | ||
Double rooms | 1,649€ | |||||
Sep 12 2026 | Sep 19 2026 | 10 | Single rooms | 2,228€ | ||
Double rooms | 1,649€ | |||||
Sep 19 2026 | Sep 26 2026 | 10 | Single rooms | 2,228€ | ||
Double rooms | 1,649€ | |||||
Sep 26 2026 | Oct 03 2026 | 10 | Single rooms | 2,158€ | ||
Double rooms | 1,579€ | |||||
Oct 03 2026 | Oct 10 2026 | 10 | Single rooms | 2,158€ | ||
Double rooms | 1,579€ | |||||
Oct 10 2026 | Oct 17 2026 | 10 | Single rooms | 2,158€ | ||
Double rooms | 1,579€ |
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