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 : 1750€
Region : Tuscany
Duration : 7 Days / 6 Nights
Level :
Type : On the way
Category : Bike
Trip : Self-guided
Activity : Hybrid
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 : 38 Miles - 61 Km 
Elevation gain 1 : 1193 Meters 

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 : 33 Miles - 53 Km 
Elevation gain 1 : 967 Meters 

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 : 34 Miles - 55 Km 
Elevation gain 1 : 933 Meters 

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 
Elevation gain 1 : 948 Meters 

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 : 38 Miles - 61 Km 
Elevation gain 1 : 1212 Meters 

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 : 57.60 Km / 35.80 Miles - Elevation gain : 1050.60 Meters

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.

Hybrid bike - Standard
FLAT BAR - ( or equivalent)

we put together the disc brake for the stability and the reliability of braking and the compact gear with 42 teeth in the back, an advanced gearing concept that helps maintain rider efficiency.

About disc brake we have the advantage of the power – it generate an incredible amount of stopping power, usually far more than is necessary to adequately stop a road bicycle and Reliable, all weather braking.
For the rest is an hybrid with straight handlebars, lightweight with hybrid wheels ad narrow tires for low rolling resistance allowing for greater speed and less exertion when riding on paved road.

  • Frame: Aluminum frame Fork: Full carbon Chain ring: Shimano Deore XT 38/28 - compact
  • Cassette: Shimano Deore XT 11/42 - 11 speed Brakes: Shimano Deore XT Saddle: Selle Italia
  • Wheel set: Shimano VH-RX010 Weight: 10 kg
  • Size: S, M, L

• 1 new bottle

• Helmet

• Odometer

• Lock

• Pump frame


1 Handlebar bag with rain cover containing : Tire levers / 2 Spare tubes / Toolkit


• Pedals are included, flat by default or toe straps on request. If you want to use your bike shoes, you should bring your own pedals + pedal wrench : we will be happy to install them on your bike.



Roadbook for Discovery allows you to travel freely with all the information you need for your trip: Stages, points of interest, itineraries with interactive guidance, travel documents.

All in offline mode, you download your file before leaving, then you have all the information necessary for your trip. (Phone not provided).


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.


Our Travelbooks are complete packages of information that will help you to guide yourself through the itinerary that we have planned and laid out. You will find information about the hotels, itinerary, regional informations...

Daily Elevation Profiles
Average / Day : Distance : 57.60 Km / 35.80 Miles - Elevation gain : 1050.60 Meters
Day 2 :   Loop tour around Siena

Option 1: 38 Miles - 61 Km  Elevation gain 1 : 1193 Meters 

Day 3 :   Chianti wine and vineyards

Option 1: 33 Miles - 53 Km  Elevation gain 1 : 967 Meters 

Day 4 :   Cycle to Greve in Chianti

Option 1: 34 Miles - 55 Km  Elevation gain 1 : 933 Meters 

Day 5 :   Ride through vineyards to San Gimignano

Option 1: 36 Miles - 58 Km  Elevation gain 1 : 948 Meters 

Day 6 :   Cycle to Volterra

Option 1: 38 Miles - 61 Km  Elevation gain 1 : 1212 Meters 


  • 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
  • Guidance Application (phone not provided)
  • 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.

Informations & Recommendations

To get to the start of your Tour (Siena), the easiest airport are Rome Fiumicino and Florence Peretola :

  • From Fiumicino aiport (Roma) take the train “Leonardo Express” to Roma train station (About30 minutes, start each half hour and is direct).
  • From Roma to Siena you will find many trains (about 3h). Then take a taxi to your hotel.
  • From FlorencePeretola (Florence) take a bus or a cab to Florence train station. Then Take a train from Florence trainstation to Siena (about 1h30). LArrived at the train station take a taxi to your hotel (about60eur).

Your Tour ends in San Gimignano. First take a taxi to Siena train station where you can take trains to Roma (3h) and Florence (1h45).

Tour rates

Contact our tour consultants for more information and an exact rate based upon your travel dates.

Price from* & per person Double occupancy Single supplement
(traveling with a group)
Standard 1750 € 400 €
*Rates vary according to hotel availability and specific start date. Please contact us for triple room rates

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


Guidance Application Included
Biking Roadbook Included
Travelbook Included

Bikes available

Bikes available Options per person
Road Bike Rental
    Standard 120 €
Electric assist bike
    Standard 160 €
Gravel Bike Rental
    Standard 150 €

Please note that any bike changes during the trip may incur an extra fee.

Services available

Services available
Cancelation insurance 6%

Bot scann is mandatory