Tuscany bike tours: the hills of Tuscany

€ 1150 (from) / Per person

Tuscany bike tours: the hills of Tuscany

This tour is a trip through time, from Etruscans tombs to Romans ruins, from Medieval hilltop towns to Renaissance basilicas. It also offers an incredible diversity of landscapes, from the vineyard-covered hills of Chianti & Brunello, to the cypress-crested mounds of the “Crete.”
Your journey will begin in San Gimignano. This walled medieval town has been designated a UNESCO World Heritage Site for its 14 feudal towers still standing & early Renaissance frescoes. From San Gimignano you will bike through the vineyard hills of Tuscany to Siena, another UNESCO World Heritage Site & home to some of the most remarkable art & architecture from the 13–15th centuries. In Siena you can enjoy a glass of wine in the piazza where the 400-year old tradition of the Palio horse race takes place, climb medieval towers, or indulge in the famous spiced cake, “panforte.” Then continue deep into the country to reach the peaceful abbey of Monte Oliveto Maggiore, founded in 1313, before continuing on to the charming hilltop town of Montepulciano, where you can enjoy breathtaking views of the rolling hillside, splendid medieval architecture, & the exquisite DOCG Nobile di Montepulciano.

  • 7 Days
  • Age 15+
  • Tuscany 


  • San Gimignano
  • Visit Siena
  • Buonconvento – Monte Oliveto Abbey
  • Montepulciano


Day 2 – Poggibonsi 

Day 2 – Poggibonsi 

Day 3 – Siena 

Day 4 – Buonconvento 

Day 5 – Montalcino 

Day 6 – Montalcino Loop 

Day 7 – Montepulciano 

How does it work

We transfer your luggage

Just leave it at the reception desk with your name tag & you will find it at your next accommodation.

We book your hotels

We will book double rooms with private bathrooms in 2- or 3-star hotels, boutique B&Bs, or agritourism estates. You will find the vouchers to each hotel in your welcome package.

We supply GPS files.

In order to be more eco-friendly, we will provide a GPX reader application with a user-friendly interface, allowing for easy and real-time navigation

Departure: San Gimignano (Poggibonsi)
Destination: Montalcino
  • 7 nights (in 3 stars accommodation)
  • All breakfast (dinners on demand)
  • Emergency number 24/7
  • Gps files
  • Luggage transfer
  • Dinners
  • Tips

Our rental bikes

Our bikes are equipped with plastic water bottle, rear pannier, lock, kit repair, spare tubes, GPS available on demand.

Tour Plan


Day 1: Arrival in Poggibonsi and settling

Where you will be met by our representative who will drive you to your villa in Poggibonsi.


Distance 40 km

Day 2: Villa S. Lucchese - Colle Val d'Elsa - San Gimignano

Departing from Villa San Lucchese first you encounter Colle Val d’ Elsa and its glass blowing artisans some of which you can visit. San Gimignano with its towers will request more time and a couple of hours of window shopping before starting back to San Lucchese


Distance 42 km

Day 3: Villa S. Lucchese - Abbadia Isola - Monteriggioni - Siena

A nice day through winding Chianti roads, in a landscape of luscious, vineyards and superb wineries to end in Siena to have an ice-cream on one of the most famous squares in Italy: Piazza del Campo.


Distance 40 km

Day 4: Siena - Buonconvento

A nice day through winding Chianti roads, while the landscape is changing from luscious, vineyards to the more linear cypress-crested hills of the “Crete” near Buonconvento. Murlo is a nice little village on your way to the nice farm where you are spending the night. In summer you will be glad to get a refreshing dip in the swimming pool or in autumn a relaxing massage and a sauna at their beautiful farm.


Distance 46 km

Day 5: Buonconvento - Montalcino

Rather difficult start, with fairly steeps slopes until you reach the asphalt. Then you head for The Monte Oliveto monastery. You will spend the night in a nice hotel in Montalcino the Brunello home land.


Distance 33 km short option 55 km long

Day 6: Sant'Antimo Abbey

Enjoy this fortified town from the bastions of which you will enjoy of a 360° view. The descending trail road lead you to the beautiful and peaceful church of Sant’Antimo where you may be able to listen to Gregorian chants. Night at the same Inn in Montalcino.


Distance 45 km

Day 7: Montalcino - Pienza - Montepulciano

A very full day as from the thermal square of Bagno Vignoni, to Pienza, the renaissance jewel redesigned by the pope Pio the II to become a “livable” town; Visit the town which is also an agricultural centre well known for pecorino cheese, and truffle production. A dirt road will take you to Montichiello a nice little village immersed in the “Crete”. you can stop there for a nice lunch or just for a cappuccino before continuing to Motepulciano known for its “Nobile” wine.


Day 8: End of our service

Transfer to Chiusi train station.

Photo Gallery