Tuscany Cycling Siena to Sansepolcro

This Tuscany Siena to Sansepolcro will let you see the typical Italian towns and villages that will take your breath away. Cycle over rolling hills, along green wheat fields, and vineyards, and don't forget to taste some famous Tuscan wines!

Grade

Moderate

When

April-Nov

Accommodation

3* & 4* star hotels

Price

From €895

E-Bike Hire

(On Request)

Bike Hire

(On Request)

Road Bike Hire

(On Request)

From: €895

Description

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
Welcome to Siena. Bike fitting. Special event of the day: A walk in Siena, the best preserved Medieval town of the world, also called "Medieval Pompeii", the Campo square, and its narrow alleys.
Day 2
Siena to Buonconvento-Montalcino - 50km
Highlights of the day: Epic ride across the hills South of Siena, the Etruscan territories of Murlo and Vescovado, the village of Buonconvento, and the nearby Abbey of Monte Oliivento Maggiore, with masterpieces of Renaissance painting. Ride details: Moderate - 50km of rolling hills, longer routes, and optional roads are available. Special event of the day: A stroll in the historic center of Montalcino.
Day 3
Montalcino, Pienza to Montepulciano - 40km / 70km
Highlights of the day: Views of Tuscan towns and countryside, 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. Ride details: Moderate - 40km of rolling hills, longer routes (+70km), and options are available. Special event of the day: Visit the town of Pienza or the small villages of the valley, some of the local wineries, and ewe cheese producers.
Day 4
Montepulciano, Monticchiello, Pienza to Montepulciano - 40km
Highlights of the day: Views of Tuscan towns and countryside, a stroll in Montepulciano, one of the most beautiful hilltop towns of Italy, an alternative ride is Pienza, or the ride to the hot springs of Bagno Vignoni. Ride details: Moderate - 40km of rolling hills, longer routes, and options are available. Special event of the day: Visit the town of Pienza.
Day 5
Montepulciano to Cortona - 40km
Highlights of the day: Views of Tuscan towns and countryside, the Montepulciano wine area, and Lake Trasimeno, the largest lake on the Peninsula. Ride details: Moderate - 40km of rolling hills, longer routes, and options are available. Special event of the day: Fantastic undulating ride with 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 - 70km
Highlights of the day: Views of the Northern Umbria woodlands and rural areas, easy riding in the Tiber River Valley, surrounded by the Apennine Mountains. Ride details: Moderate - 70km of climbing, longer routes, and options are available. Special event of the day: Do not miss the frescoes by Piero della Francesca in Sansepolcro!
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!



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  • All prices are based on double rooms.
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  • 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 (On Request)
  • E-bike (On Request)
  • Road bike (On Request)
  • Airport/Railway station transfers

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