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!
BIKE INCLUDED
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.
Accommodation : La Villa Di STR - "Siena"
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.
Accommodation : La Villa Di STR - "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.
Accommodation : Hotel Palazzo Squarcialupi - "Castellina In Chianti"
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.
Accommodation : Hotel Palazzo Squarcialupi - "Castellina In Chianti"
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.
Accommodation : Hotel Antico Pozzo - "San Gimignano"
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.
Accommodation : Hotel Antico Pozzo - "San Gimignano"
Day 7 : Leave Tuscany
According to your program, we can arrange accommodations and transportation.
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 |
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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.
• 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.
Hybrid bike - Standard
FLAT BAR - ( or equivalent) INCLUDED 
With drop handlebars, these bicycles are built for traveling at higher speeds on paved roads, sometimes referred to as racing bikes. Our race bikes are all brand-new, reliable, and well maintained for your ideal cycling experience of Italy. Extremely efficient, incredibly smooth to ride and will take you everywhere with stability after a professional bike fitting session. Race bike with drop handle bar is strongly suggested if you use regularly those bike!
Road bike - Standard
FULL CARBON FIBER - ( or equivalent) with supplement (120€) 
Electric bikes are regular pedal bikes that provide electric assistance whenever you want.
Electric assist bike - Standard
E-BIKE SCOTT E-SUB CROSS 10 - ( or equivalent) with supplement (160€) 
New Scott Addict Gravel 20 with drop handle bar, a cyclocross touring oriented , disc brake and wider tires to enjoy the classic strade bianche in Tuscany: Eroica itinerary and Francigena path. Our gravel bikes are all brand-new, reliable, and well maintained for your ideal cycling light off-road experience of Tuscany. Lightweight because of carbon fiber frame, hydraulic disc- brake,these bikes can perform on both the road and off the road.
Gravel bike - Standard
BIKE SCOTT ADDICT 20 - ( or equivalent) with supplement (150€) |
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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. |
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Hybrid bike - Standard
FLAT BAR - ( or equivalent)
INCLUDED
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.
Accessories
INCLUDED
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).
INCLUDED
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.
INCLUDED
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...
Option 1: 38 Miles - 61 Km Elevation gain 1 : 1193 Meters
Option 1: 33 Miles - 53 Km Elevation gain 1 : 967 Meters
Option 1: 34 Miles - 55 Km Elevation gain 1 : 933 Meters
Option 1: 36 Miles - 58 Km Elevation gain 1 : 948 Meters
Option 1: 38 Miles - 61 Km Elevation gain 1 : 1212 Meters
Included
- 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 € |
This tour is available at any day from the 1st of April to the end of October and is not suitable for children.
Accessories
| Accessories | |
| 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% |
Todd
United States
It was amazing. We had such a wonderful time and all of the routes were incredible, simply spectacular. The weather was perfect (very lucky) and just had an excellent time touring through Tuscany this way. THe hotels were all great, especially in Castellina and San Gigminano - and the bikes - totally top notch, no problems. Gigi and Marco from Cicloposse were excellent and responsive, great guides. Couldn't have asked for anything more ok this trip. We will definitely be booking again for something in the future. Sicily ??? Best,
Casual : Beginners and occasional cyclists. Easiest tours we provide. Typically flatter terrain, no notable hills or anything of a steep gradient.
Hobby : Weekend riders. People with some cycling experience, rolling countryside, possible short climbs.
Active : Cyclists with experience on longer rides. Hilly terrain with reasonable amount of climbs and difficulty
Pro : Avid cyclists, ride every week and love long and challenging rides. Dream on riding the Tour de France cols.
Comparison chart : (15km/hrs)
| Average dist (miles) | Average dist (km) | Elevation max/day (m) | Average hours | |
|---|---|---|---|---|
| Casual |
< 28 | < 45 | < 300m | 3-4 |
| Hobby |
18 - 35 | 30 - 55 | 300-550m | 3-5 |
| Active |
30 - 60 | 50 - 100 | 550-1000m | 4-6 |
| Pro |
> 60 | > 100 | > 1000m | > 5 |
Some of our tours can be in 2 different level, we have itinerary for both versions
Casual : Beginners and occasional hikers. Typically flatter terrain with just rolling hills.
Hobby : Weekend hikers. People with some experience hiking around trails.
Active : Hikers with experience on longer hikes. Hilly terrain with some steep gradients.
Pro : Randonneurs avides, randonnée chaque semaine et adore les longues et difficiles randonnées.
Comparison chart : (4km/hrs)
| Average dist (miles) | Average dist (km) | Elevation max/day (m) | Average hours | |
|---|---|---|---|---|
| Casual |
< 6 | < 10 | < 150m | 2.5 |
| Hobby |
6 - 9 | 10 - 15 | 150-300m | 25-375 |
| Active |
9 - 11 | 11 - 18 | 300-450m | 3.75 - 4.5 |
| Pro |
> 11 | > 18 | > 450m | 4.5-6 |
Some of our tours can be in 2 different level, we have itinerary for both versions