Tuscany Wine Tour

On this bike tour around Tuscany, you will discover the beauty of this Italian region, home of the Chianti wine.
Start your tour in Siena, a medieval town and UNESCO World Heritage Site. From there you will be able to explore the charming villages and surrounding vineyards that make Tuscany so special. Cycle through Castellina, Radda, and Greve, and enjoy wine tours and fresh local food.
The tour then brings you to San Gimignano, with cycling through more vineyards, and includes a day in Volterra, an ancient Etruscan town.
Whether crowned by timeless villages, covered by vineyards and olive groves or strewn with wildflowers, the hills of Tuscany have one thing in common: they're perfect for exploring on two wheels!

Price from : 1590 €
Region : Tuscany
Duration : 7 Days / 6 Nights
Level : Active
Trip : Self-guided
Activity : Biking
Dates : Starts any day

Click below to see hotels versions.

Day 1 :   Arrive in Siena, Tuscany

Arrival at the hotel in Siena on your own. Siena is a medieval city with beautifully preserved Gothic architecture. The entire city of Siena was built around the Piazza del Campo. Here you will have time to shop while exploring the many hidden medieval walkways. Meet and Greet, we will fit your bikes and introduce you to each day's ride.

Day 2 :   Loop tour around Siena

Distance 1 : 37 Miles - 60 Km 

On this day, the ride explores Montagnola Senese, passing through several charming, little medieval villages and 'borgo' boroughs: Sovicille, Ancaiano, Simignano, Pieve Scola. You will riding along the Via Francigena, and ancient road and pilgrim route running all the way from France to Rome. Here, you will notice the subsoil, mainly made of limestone and full of marble, including the famous yellow marble used for the Duomo of Florence. After making the loop back to Siena, you'll enjoy the night at your hotel in Siena.

Day 3 :   Chianti wine and vineyards

Distance 1 : 31 Miles - 50 Km 

On today's route you can stop at Castelnuovo Berardenga, a medieval town which marks the gateway to Chianti country. From here you will ride inside the vineyard of famous Chianti classico wine passing through many little hamlets. Not-to-be-missed is Castello di Brolio, a castle and winery. There is also the chance to shop at a first-class ceramics workshop just before Radda in Chianti. Arrive in Radda in time for a light lunch and enjoy the last 10 km of gentle rolling hills to get to Castellina.

Day 4 :   Cycle to Greve in Chianti

Distance 1 : 32 Miles - 52 Km 

Today you will bike along quiet roads to the three villages that formed the Chianti Alliance centuries ago. Visit Tuscany's forgotten abbeys and hamlets, then enjoy a winery tour and taste their supple reds, fresh honey and rich olive oil. Have a stop at Greve's main piazza, characterized by an original formation of an irregular triangular shape, defined by beautiful long porticos. Back via Panzano with preserved old walls, gates and the keep of the medieval castle. Relax by the infinity pool spilling into the countryside of endless vineyards.

Day 5 :   Ride through vineyards to San Gimignano

Distance 1 : 36 Miles - 58 Km 

More vineyards await you today, but you will be amazed at how different they look once you get into the district of San Gimignano. Soon you pass Monteriggioni, literally a town-in-a-castle. Barely two hundred yards across, its eighty residents all reside within the picture-perfect round turreted walls that crown the hilltop visible for miles around. Soft, colorful, rolling hills of vineyards and sunflowers provide the backdrop to pre-Roman Etruscan remnants on your route to San Gimignano's "medieval skyscrapers" in the distance you will see the seventeen towers.

Day 6 :   Cycle to Volterra

Distance 1 : 37 Miles - 60 Km 

Today you will leave San Gimignano behind and cycle to the ancient Etruscan town of Volterra. Through a patchwork-like landscape dotted with wheat fields, olive groves and villas, you reach the base of the imposing hill upon which the town is set. One more solid climb before you arrive in the old town. The "magic and mysterious" city of Volterra has its roots in three thousand years of history. It is possible to find evidence and traces from every historical period which gives the artistic city a unique aspect. Back to San Gimignano via another scenic back road.

Day 7 :   Leave Tuscany

According to your program, we can arrange accommodations and transportation.

Average / Day : Distance : 56.00 Km / 34.60 Miles

Click below to see hotels versions.

Day : 1, 2

The Villa of Str, Located just outside the old city walls of Siena, The Villa is a charming liberty style residence dating from the early years of the twentieth century and within easy walking distance from the historic centre of Siena. Offering solutions for all needs, whether as a family, a couple, with friends or even with your pets, all our rooms are tastefully decorated with respect for the aesthetic and historical origins of the building. Whatever your reasons for visiting Siena, our hotel will prove welcoming, stylish and comfortable, a great base from which to explore the medieval town of Siena.

Day : 3, 4

Managed directly by the owner, Albergo Palazzo Squarcialupi is a historic property in Castellina in Chianti. It offers grounds with outdoor swimming pool, and a spa. Rooms are complete with sitting area. The rooms of Palazzo Squarcialupi feature rustic terracotta floors, exposed wood beams on the ceilings, and 18th-century furnishings. The bathrooms are in Carrara marble.

Day : 5, 6

Hotel L'Antico Pozzo, the style hotel in San Gimignano, is not only a fine period residence but also a place where the stories,legends and magic of San Gimignano come alive. Before being transformed into an elegant hotel, in the 17th Century the L'Antico Pozzo, or "TheAncient Well" was a convent. For both lovers of history and culture, and fans ofintrigue and elegance, hotel rooms offer you the utmost comfort in a trulymagical and evocative atmosphere. Discreet elegance, typical of theancient medieval noble palaces joins the eighteenth century-inspired decor andtraditional Tuscan style, while maintaining all the conveniences of acontemporary hotel. From the nightfall until breakfast, you will relivehistory in this old building.

Bikes available for your tour

The characteristics of this bike are presented as an example and are not guaranteed
Please note that any bike changes during the trip may incur an extra fee.

FLAT BAR - ( or equivalent)
Hybrid bike - Standard

Hybrid bikes blend the characteristics of race bikes and mountain bikes. Hybrids typically have the flat, straight handlebars that provide a fairly upright sitting position and are designed to reduce shoulder and neck fatigue.

Our hybrids are lightweight, with road wheels and narrow road tires for low rolling resistance allowing for greater speed and less exertion when riding on paved roads.



GPS are included on most of our tours since 2008. We change the units every 2 years and always invest in the best models. Simple to use, easy to read, yet sophisticated devices they are available on all of our tours. The routes described in your roadbook are stored as tracks in the GPS unit. You simply have to follow the line shown on the GPS, and enjoy. 1 GPS for every 1-3 people


Our roadbooks are complete packages of information that will help you to guide yourself through the itinerary that we have planned and laid out. We have invested significant time and incorporated the feedback of our customers over many years (since 1997!) to make our roadbooks even better. Our roadbooks include: color maps, highlighted routes, touristic information, orientation points to reach hotels, and easy to follow step by step directions (cue-sheets). Please note that for custom itineraries you will not have cue sheets. Only maps and GPS routes.

Rates vary according to the availability of hotels and seasons.
Contact our sales team for more information and an exact rate based upon your travel dates.


  • 6 nights of accommodation in superior hotels of charm with private shower and/or bath
  • Daily breakfast at each hotel, 1 dinner included
  • Orientation in person with our local guide
  • Hybrid bike rental included
  • Detailed ROAD BOOK, including details maps, touristic information, step by step itinerary and cue sheets
  • 1 GPS GARMIN OREGON 450T for 2 people
  • All luggage transfers
  • Comprehensive trip literature
  • Technical and emergency support available at all times

What's not included

  • Airfare to and from the trip
  • Lodging before and after the trip
  • Drinks
  • You have to pay local taxes each day (0.70 to 2.50 eur) in cash to each hotel (tourist administration tax)
  • Some meals are not included in each destination, which gives you the opportunity to explore regional cuisine on your own. You will find all information needed with our team support in your roadbook.

Price from & per person Double occupancy Single supplement
(traveling with a group)
Standard 1590 € 350 €

This tour is available at any day from the 1st of April to the end of October and is not suitable for children.

*Please contact us for triple room rates

GPS Included
Biking Roadbook Included
Bikes available Options per person
Hybrid Bike Rental Included

Please note that any bike changes during the trip may incur an extra fee.
Bot scann is mandatory