April- Nov


3 & 4 star hotels


from € 895

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€ 175 E bike

Bike hire

€ 105 Trekking bike

Bike hire

€ 150 road bike

From: 895


Tuscany Cycling Siena to Sansepolcro

Tuscany Cycling Siena to Sansepolcro. Self-guided cycling Trip from Tuscany Siena to Sansepolcro. From April 1 until November 15
For guided options from 4 persons or more send us an email.

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E-Bike Cycling holiday Siena Tuscany to Sansepolcro

This wonderful cycling trip in Tuscany from Siena to Sansepolcro features many highlights. This self-guided trip will let you see the typical Italian towns and villages that take your breath away. Relax in one of the local Italian restaurants after a day in the saddle. Cycle along the rolling green wheat fields and numerous Tuscan vineyards. Most important: Keep your eyes open while peddling!

Your first bike day starts in medieval Siena over the epic hills of South Siena. You’ll find in Monte Oliveto Maggiore masterpieces of Renaissance painting. Wander through Montalcino historical center and visit on your third bike day Pienza the dream town of Pope Pius II moreover the place of architectural masterpieces. Around Montepulciano don’t forget to visit some local wineries, olive mills, and also local cheese producers.

The Montepulciano wine area and Lake Trasimeno (the largest lake on the Peninsula) are top-class highlights. Last but not least Cortona – Sansepolcro is the final stage On your last cycle day you get great views of the Northern Umbria woodlands and rural areas before finally arriving at your last destination Sansepolcro. Sansepolcro is famous due to the frescoes by Piero della Francesca.

Cycle Tuscany and immerse in a fantastic self-guided cycling trip in Italy!

  • The start of this cycle tour is in the UNESCO world heritage city of Siena and  discover Siena probably the best preserved Medieval town in the world
  • The small villages on your way through Tuscany with local wineries, olive mills, and cheese producers.
  • Tuscan countryside
  • The Montepulciano wine area as well as Lake Trasimeno
  • Views of the Northern Umbria woodlands and rural areas
  • Lake Trasimeno: the fourth largest lake in Italy surrounded by green rolling hills covered with olive trees
  • Relax in one of the local Italian restaurants after a day in the saddle
Day 1
Check in
Check-in around 14.00 at your hotel in Siena. This beautiful city will be your starting point for the upcoming week. Depending on your time of arrival you can visit the city of Siena.
Day 2
Siena to Montalcino 50 km
Today starts your cycle day at Siena you cycle an epic ride across the hills of south Siena, the Etruscan territories of Murlo and Vescovado. After this, you arrive at the village of Buonconvento. From here you go to Monte Oliveto Maggiore (extension) with masterpieces of Renaissance painting. At the end of this cycle day, you arrive at Montalcino with its historic center.
Day 3
Montalcino to Pienza to Montepulciano 40 km
Your third day of the Trip will start at Montalcino on this day you’ll see Pienza the dream town of Pope Pius II place of architectural masterpieces, a shop for ceramics, and sample delectable pecorino cheese, the small hamlets of the Val d'Orcia. Visit some of the local wineries, olive mills, and ewe cheese producers. Your cycle day ends in Montepulciano.
Day 4
Montalcino to Monticchiello to Pienza to Montepulciano 40 km
On this day you cycle from Montepulciano one of the most beautiful hilltop towns of Italy to Monticchiello to an alternative ride Pienza or the ride to the hot springs of Bagno Vignoni. From Bagno Vignoni you go to the town Montepulciano where you started this cycle day.
Day 5
Montepulciano to Cortona 40 km
On day 5 we start from Montepulciano, You’ll visit the Montepulciano wine area and Lake Trasimeno, the largest lake on the Peninsula. Cycle a fantastic undulating ride with a final climb to Cortona with vistas on Lake Trasimeno and Chiana. A glass of local wine in the Wine bar on Cortona’s Corso.
Day 6
Cortona to Sansepolcro 70 km
Today is your last cycle day get great views of the Northern Umbria woodlands and rural areas, and easy riding in the Tiber River Valley surrounded by the Apennine Mountains. Your last stop is Sansepolcro. Do not miss the frescoes by Piero della Francesca.
Day 7
Departure day
Departure day... Time to say goodbye, a good flight back home, or else a pleasant stay in Tuscany. Transfers to the (on request) according to the time of your flight!


  • Florence International Airport is named after one of the most famous Italians – Amerigo Vespucci. There is no train connection to the airport. From Florence railway station there are good connections to all kinds of cities in Italy. The airport lies only four kilometers away from Florence. Shuttle buses leave every 30 minutes. Florence Airport is only 75 kilometers away from Siena.


  • Siena railway station opened in 1935, it is the terminus of the lines to Empoli, Lucca, Grosseto, and many other places in Tuscany. Florence to  Siena, the train ride duration is 1h 30min. The trains leave every 30 minutes.

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Booking Information

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  • All prices are based on double rooms.
  • All day departures
  • For bookings and inquiries contact us at

Extra Information

  1. Fill out and submit the online booking request or send an email to
  2. We tend and try to send all over within 48 hours.
  3. Please do not make travel plans until you receive our confirmation.
  4. Please be advised that we make every effort to ensure that all the information given on this site is accurate. All statements and information have been researched and supplied by third parties.
  5. The information given is accurate and reliable, to the best of our knowledge. Should errors be found, we will rectify them as quickly as possible. However, we accept no responsibility for errors or inaccuracies.
  • 6 Nights in boutique hotels, B & B, or Agriturismo
  • Bike Tour presentation (welcome meeting and bike fitting)
  • Baggage transportation from hotel to hotel
  • Supply of road notes and maps
  • Telephone assistance
  • Lunches
  • Dinners and Local Taxes
  • Admission to museums and archaeological sites
  • High season supplement
  • Single room supplement
  • Trekking Bike €105
  • E-bike €175
  • Road bike €150
  • Airport/Railway station transfers




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