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Tuscany’s Jewels and Treasures

Rouler à vélo à travers les vignobles en Toscane 5
This cycling tour ends in Florence Admire the tilted tower of Pisa Cycle the vineyards of the Tuscan countryside The itinerary takes you pass cozy countryside villages Cycle to some of Tuscany's historical monuments
Rouler à vélo à travers les vignobles en Toscane

Tuscany’s Jewels and Treasures

  • Level
  • PriceFrom 730 euros
  • DAY7 nights / 8 days

More info: Receive detailed hotel list, bike specs, and route description

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For leisurely riders, Tuscany’s Jewels and Treasures is perhaps the best way to enjoy Tuscany on an independent cycling tour. You will travel on a variety of routes, experiencing all the wonders Tuscany has to offer; from fine panoramas to culture and of course, their delicious cuisine! This unique route starts in Pisa, home to its famous Leaning Tower and passes through Siena and on to the Tuscan capital, Florence via the “road of wines”. During your adventure, you will ride through bustling, medieval towns, preserved Tuscan villages, and rich hillsides filled with wineries. This 8-day adventure is perfect for small groups and individuals looking for pleasurable, less rigorous routes within the Tuscany region.

For a more challenging route, we recommend our 6-night/7-day Giro of Tuscanywhich also starts from Pisa and ends in Florence.


For travel and cycling tips to Tuscany, visit our "travel and cycling tips" section.


D1Saturday: Arrival in Pisa


Arrive into Pisa, a city known worldwide for its magical Piazza del Miracoli and its famous leaning tower. There is more to this city than just the Tower though; it is home to over 20 historical churches and numerous museums. Be sure to spend some time wandering around this friendly and lively university city to experience its wealth of art and gastronomy as well! After a day of exploration, take the time to relax ahead of your first day of cycling tomorrow.


D2Sunday: Pisa – Casciana Terme Mileage: 47 km / 29 miles; Total Climb: 230 m / 755 ft; Total Descent: 120 m / 394 ft


After being kitted out with your bikes (if you are hiring with us) in the morning, it is time to start your journey! You will ride along the River Arno passing through Pontedera. This rather modernized district is home to the wine company Castellani and a sweets factory called Amedei. From here the route takes you through vineyards and olive groves, a real immersion into Tuscan countryside! You will reach the thermal town of Casciana Terme, famous for its Etruscan heritage, where you will overnight. Note that if the day’s route length looks to be a bit daunting then you can shorten it by taking the train.


D3Monday: Casciana Terme – San Gimignano/Colle Val d’Elsa Casciana Terme – San Gimignano: Mileage: 49 km / 30 miles; Total Climb: 680 m / 2,231 ft; Total Descent: 510 m / 1,673 ft; Casciana Terme – Colle Val d’Elsa; Mileage: 69 km / 43 miles; Total Climb: 910 m / 2,986 ft; Total Descent: 890 m / 2,920 ft


Today your itinerary follows the Via Francigena, an ancient pilgrim route running from France to Rome and on to Apulia. You will ride through beautiful rolling countryside and vineyards on towards the village San Gimignano, your destination for the day. This hilltop hamlet is a UNESCO World Heritage site and famed for its numerous towers. The combination of its setting atop a hill and the village’s striking towers makes for a truly memorable sight!

Depending on your accommodation choice you may be staying in Colle Val d’Elsa which adds 20km to the ride.

D4Tuesday: San Gimignano/Colle Val d’Elsa – Siena San Gimignano – Siena Mileage: 49 km / 30 miles; Total Climb: 650 m / 2,133 ft; Total Descent: 620 m / 2,034 ft; Colle Val d’Elsa - Siena Mileage: 29 km / 18 miles; Total Climb: 400 m / 1,312 ft; Total Descent: 230 m / 754 ft


Continue to follow the Via Francignea today from San Gimignano. Proceed towards Colle Val d'Elsa, Italy's Bohemia, an industrial village known for its artisan glassware. Walk around the workshops and indulge in the local culinary offerings. Abbadia a Isola is your next stop, a remarkable Roman abbey. You will soon be welcomed by the views of Mount Maggio and the castle of Monteriggioni, Dante's subject in his famous literary pieces. Siena is just ahead; easily distinguished by old brick buildings and the crown of Torre del Mangia. Slow down and enjoy the views as you arrive into this beautiful city.

Note that if you stayed at Colle Val D’Elsa todays ride is 20km shorter.

D5Wednesday: Siena – Radda in Chianti Long Option; Mileage: 45 km / 28 miles Total Climb: 880 m / 2,887 ft Total Descent: 700 m / 2,297 ft; Short Option; Mileage: 37 km / 23 miles Total Climb: 680 m / 2,231 ft Total Descent: 500 m / 1,640 ft


From Siena head north towards the stunning village of Radda in Chianti. First stop along the way is Castagnolli, where you can admire the Brolio Castle, now home to the Ricasoli family (and a well-managed wine cellar too!) Next up is Meleto Castle; it’ll be easy to find—it’s the beautiful Tuscan villa perched upon the hilltops. Wend your way on to Radda in Chianti. This classic Chianti village is nestled inside the verdant hill regions and cradles remnants from the Etruscan age. From here, you can see the Pretorio Palace, discover wine tours, and enjoy a leisurely stay at a nearby hotel.


D6Thursday: Radda in Chianti – Greve in Chianti Long Option; Mileage: 40 km / 25 miles Total Climb: 540 m / 1,772 ft Total Descent: 830 m / 2,723 ft; Short Option; Mileage: 18 km / 11 miles Total Climb: 200 m / 656 ft Total Descent: 490 m / 1,607 ft


Today you will discover Tuscany’s “Road of Wines” where the famous Chianti Classico wine is produced and home to the Chianti Classico Wine Festival held every September. Ride along this wine route, discovering well-preserved villages with fine shops, filled with the best wine and other local products. Pass by the baroque villages of Panzano and Montefioralle. Breathe in the fresh air and perhaps enjoy a picnic with your friends during one of your stops; or experience the local cuisine at a trattoria for a little feast. The route leads you through this beautiful Tuscan countryside into Greve in Chianti where you will spend the night.



D7Friday: Greve in Chianti – Florence Mileage: 37 km / 23 miles Total Climb: 650 m / 2,133 ft Total Descent: 830 m / 2,723 ft


Your final destination is Florence, capital of Tuscany and famed for its wealth of culture, architecture and art. Along the way, you will pass through Mercatale, a small town offering a peek into the Chianti countryside and where you will have the chance to do some wine-tasting in the local cellars. Continue on to Impruneta, filled with terracotta art! Florence awaits; the capital of Tuscany, is famed for its wealth of culture, architecture, and art, and is considered the birthplace of the Renaissance. Depending on when you arrive you may like to fit in a visit to the giant Duomo, drop by the Uffizi Gallery or discover hole-in-the-wall bars and cafes for a gastronomic treat. At the end of the day make your way to your hotel and let your legs rest from days of leisurely pedaling.


D8Saturday: Departure


After breakfast, you can spend your last moments in Florence as you wish. You may want to walk down the bridge over the river Arno and see the sun illuminating the city with different moods, choose to shop in high-end boutiques or bustling pop-out markets, or visit some of Florence’s landmarks that you didn’t manage to fit in the day before. Then pack up your luggage and move on to the next stage of your journey.  

Booking & Prices

  • Option A
  • 7 nights in 3-star hotels

  • 730 euros per person in March, April and October. Single supplement is 210 euros
  • 855 euros per person in May, June and September. Single supplement is 220 euros
  • 880 euros per person in July and August. Single supplement is 230 euros
  • Option A+
  • 7 nights in 3- and 4-star hotels

  • 830 euros per person in March, April and October. Single supplement is 265 euros
  • 955 euros per person in May, June and September. Single supplement is 275 euros
  • 980 euros per person in July and August. Single supplement is 285 euros

These prices include:

  • 7 nights’ accommodation 
  • Daily breakfast
  • Meeting with our local representative
  • Luggage transfers
  • Marked maps and/or cue sheets and route notes
  • Tourist information
  • Assistance if necessary (you will be provided with our local rep’s mobile number)
  • All tax and service charges

These prices do not include:

  • Nominal city taxes, to be paid in cash directly at each hotel (total of approx. 15-18 euros).
  • Expenses of a personal nature
  • Travel insurance
  • Bicycle rentals. Hybrid bikes are available at the rate of 105 euros per bike. E-bikes are available at the rate of 215 euros per bike.

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