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Explore quintessential Tuscany: the Chianti area, Siena, and Val d'Orcia. 

While Tuscany does not need any presentation, it never disappoints. The area south of Florence, around Siena and in the Val d’Orcia, will set the stage for our exploration by bike. You will visit medieval hilltop towns, abbeys, and wineries. We start in the countryside in the village of Greve in the Chianti area. From there, we will explore part of the Chianti production area with a visit to a winery. Siena is the embodiment of a medieval city and it will be our stay for two nights. We organized a walking tour to fully appreciate this UNESCO site. We'll immerse ourselves in the spirit of L’Eroica, a special "race" from every point of view, with surroundings and scenes from the "heroic" time of cycling: sections on dirt roads, vintage refreshments, wonderful and demanding roads. We should mention that this area has been known since Roman times for its thermal springs. We will pay a visit to the quaint village of Bagno Vignoni.

Val d’Orcia Natural and Cultural Park

The natural features of the valley, together with the cultural identity of the community that has lived there for centuries, make Val d’Orcia a unique area and for that reason it’s been designated a World Heritage site by UNESCO. The municipalities of Val d’Orcia are Castiglione d’Orcia, Montalcino, Pienza, Radicofani and San Quirico d’Orcia.

Mount Amiata

The first thing you should probably know is that Mount Amiata was/is a volcano, however geological studies show that there has never been an actual eruption and that magma overflows created, layer after layer, a "pile" that reached  the respectable height of 5,695 ft (1,736 mt). Mount Amiata, the only volcano in Tuscany, shows its unmistakable, yet lonely outline also when viewed from a distance. An island that seems to be floating across a sea of gentle hills, it does not seem to belong there and locals proudly regard it as a "different" place, a hideout, and a distraction.  There’s more than unpolluted nature, as there are several historical hamlets dating back to the Middle Age.

Not sure if you can do it? Contact us to schedule a call about how demanding the rides are or about reserving and B-bike.


  • Two important wine regions: Chianti and Montalcino-Brunello 
  • UNESCO World Heritage Sites of Val d’Orcia and Siena 
  • Villages of Montalcino and San Giminiano  
  • Stunning cycling along rolling hills covered with vineyards and quaint medieval villages
  • The thermal spa of Bagno Vignoni       
  • Mount Amiata
  • Some of the best regional food in Italy

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USD 3,465

Private room (single supplement) USD 495


6 days (5 nights)



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Overall, you exceeded my expectations. I was so blown away by this trip. One of the best experiences I have had since doing these types of trips.

Amanda Blackburn Tuscany Cycling Tour

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Day by Day

[fa icon="plus"] Day 1

Greve in Chianti - 28 mls - Rolling

Your guide will meet you in Florence for a morning shuttle. You will settle in the picturesque village of Greve in the Chianti wine region. After meeting your bikes and some bike fitting we will head out for our first ride. Today’s ride is a roller coaster journey along beautiful ridges and gentle hills through stunning countryside. We are in the Chianti Classico production area. An overview of the tour will lead to a typical Tuscan dinner at the renowned hotel restaurant. Our table will be on the terrace right over the main square. Homemade pasta and a taste of the local Chianina beef - a Tuscan staple - will be part of our menu.  

[fa icon="plus"] Day 2

Chianti and Siena - 45 mls - Hilly

We will ride through the region on Via Chiantigiana, a panoramic road that runs north-to-south across vineyards and through hilltop villages like Panzano and Radda. No doubt, we will make a stop at a Chianti Classico producer. One of the highlights of the day is a stop at the sleepy village of Gaiole in Chianti. The Eroica ride put Gaiole on the map and every year on the first weekend of October thousands of riders take over the village on their vintage bikes wearing pre-lycra cycling kits. A market with historical bicycles and other equipment fills every square. Just imagine all of that as we stop for a coffee in the piazza and grab an Eroica-branded souvenir.

Dinner in the center of Siena is at our favorite trattoria. For additional sightseeing in Siena, climb to the top of the Torre di Mangia in the Campo for an unforgettable view.

[fa icon="plus"] Day 3

Siena - San Giminiano - 28 or 50 mls - Hilly

Today is an optional rest day. You could visit Siena on your own and do some shopping, but also enjoy the view of magnificent hills surrounding Siena while enjoying your cappuccino on the hotel panoramic terrace. The loop ride is to San Gimignano, one of Tuscany's best-preserved medieval cities. There are 15 remaining towers that you can spot from far away and that dominate the narrow streets and piazzas. Another interesting stop is the walled village of Monteriggioni, one more Tuscan gem that we included in this cycling trip. The riding terrain is undulating and it alternates between forests and farmland.

We have an afternoon walking tour of Siena that we highly recommend you to join.

[fa icon="plus"] Day 4

Montalcino - Val D'Orcia -  43 mls - Hilly

Today we will change locations and move to the Brunello wine production area. We approach Montalcino via the Crete senesi landscape. Crete senesi are literally "Senese clays" and the distinctive grey coloration of the soil gives the landscape an appearance often described as lunar. We’ll regroup at a panoramic point near Asciano for photos. This hilly ride will end up at a family-owned Brunello winery for a late lunch. You will learn so much more about the area, and about Brunello. Brunello is the best red wine in Tuscany and its elegance is perhaps unsurpassed among Italian red wines. More stunning views!

In the afternoon we will make time for the thermal spa at Bagno Vignoni. Bagno Vignoni is a tiny spa town, whose sulfur springs have been known since Roman times. This naturally hot water spurts forth from the earth beneath Monte Amiata.

[fa icon="plus"] Day 5

Montalcino - Mt Amiata - 40 mls - Hilly

Today’s ride covers another area of Val d’Orcia with the goal to make it to Mount Amiata for a beautiful climb in its cool forest. While these places might not sound familiar, they are very important to the locals. Crossing the Orcia River, which gives its name to the UNESCO-recognized valley, we enter a less-touristy Tuscany dotted by a number of medieval villages. Our goal today is the climb of Mount Amiata, and lunch on the way down will feature more local specialties. This mountain is an ancient volcano, now dormant, that is over 5,600 ft high.

Back in Montalcino, you can enjoy the Tuscan sunset with a glass of wine before our celebratory dinner.

[fa icon="plus"] Day 6


Transfer to the Florence airport after breakfast.


What's Included

Bianchi Intenso Ultegra-105

Bianchi Via Nirone SBianchi Via Nirone S

 • Two professional tour guides throughout the program

• All accommodations in one 3-star hotel and two 3-star hotels

• All breakfasts, all lunches, and four dinners

• Wine and beer with meals, coffee, cappuccino, and gelato stops

• Tastings of wine and local specialties

• Entrance to thermal spa

• Logistical support during the tour and luggage transfer

• Guided tour of Siena

• Shuttle at the beginning and at the end of the tour

• All activities mentioned in the day-by-day description

• Bianchi bike rental 

• GPS navigation and maps (digital)


• Airfare
• Pre-tour hotel stays and post-tour hotel stays
• Personal expenses such as laundry and cell phone
• Guide gratuity
• Optional tour extension






Hotel Dei Capitani Montalcino_web


More Info

Food and Wine

It's often pointed that Tuscan cooking has its roots in "cucina povera" - peasant cooking. In truth, though, that can be said of most Italian cuisines. It's true, though, that Tuscan cooking is a simple one. There are no reductions, no fancy sauces, no elaborate creations, no heavy complicated seasoning. Throughout Tuscany, olive groves and wild herbs are everywhere. Many of the best olive oils produced in Tuscany are reserved for use as a condiment at the table, rather than as an ingredient in cooking in the kitchen. Some of the best Italian reds are produced in Tuscany: Chianti, Brunello, Nobile di Montepulciano, not to mention the super-tuscans.


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