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Explore quintessential Tuscany: the Chianti area, Siena, Val d'Orcia, and Maremma on this mixed-terrain bike tour.

We've designed an itinerary filled with “white roads,” interesting stops, and authentic beauty. While Tuscany does not need any introduction, it never disappoints. The area south of Florence, around Siena and in the Val d’Orcia, will set the stage for the first part of our exploration by bike. You will visit medieval hilltop towns, abbeys, and wineries. We finish on the Tyrrhenian seacoast in the Maremma region (a natural reserve).

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 stop at a winery. Siena is the embodiment of a medieval city and it will be our stay for one night. We've organized a walking tour to fully appreciate this UNESCO site. Together, 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 thermal water site of Saturnia with its unique pools.

This itinerary belongs to Tourissimo's Ambitious Tours lineup and it is meant for experienced cyclists. But do remember that it is a vacation and that you can ride as little or as much as you want, or take a day off altogether. 

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


  • Two important wine regions: Chianti and Montalcino-Brunello 
  • UNESCO World Heritage Site (Val d’Orcia)
  • Villages of Pienza and Montalcino
  • Stunning cycling along rolling hills covered with vineyards and quaint medieval villages
  • Some of the best regional food in Italy
  • Strade Bianche
  • Gaiole in Chianti, the home of l’Eroica
  • Siena
  • The lunar landscape of Crete Senesi
  • The historical Via Francigena (Francis Way, and ancient pilgrimage route)
  • Earthy food and uplifting wines
  • Espresso and cappuccino stops in charming medieval villages
  • The thermal waters of Saturnia
  • Lesser-known Maremma villages of Sorano, Capalbio, Pitigliano 

Featured in Forbes Tuscany Strade Bianche



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USD 4,250

Private room (single supplement) USD 695


8 days (7 nights)



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The tour was fabulous and far exceeded my expectations. 

Mitch Stimac Tuscany Strade Bianche

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Day by Day

[fa icon="plus"] Day 1

Greve in Chianti - 23 mls - Rolling

Your guides will meet you at Florence airport for a late morning shuttle. You will settle in in the picturesque village of Greve in the Chianti wine region.  After preparing the bikes and some bike fitting we will head out for a warm-up ride. An overview of the tour will proceed a typical Tuscan dinner. 

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 - 52 mls - Hilly

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. We will ride a loop through the region on Via Chiantigiana, a panoramic road that runs north-to-south across vineyards and through hilltop villages like Radda and Castellina. We’ll have a regroup and wine tasting at the Castello di Brolio on the Barone Ricasoli estate. It is one of the largest – the first one for sure – of all Chianti Classico producers. 

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 second 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.

[fa icon="plus"] Day 3

Siena - 45 or 68 mls - Hilly

Your Tuscany trip also features Siena, where a medieval air lingers amidst the twisting streets of warm, brown brick. Strolling Siena’s narrow maze of cobblestone walkways is an amazing architectural journey. The whole city of Siena, built around the Piazza del Campo, is renowned for its horse race called Palio. The riding terrain is undulating and it alternates between forests and farmland.  We approach Siena 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.

The Strade Bianche pro race has had some epic finishes on the final cobblestone climb in Siena. And that's where we will head for a walking tour and dinner. 

[fa icon="plus"] Day 4

Montalcino - Val D'Orcia -  51 mls - Hilly

Today we will change areas and move a little bit south to the Brunello di Montalcino wine production area. We pedal on a ridge just above the Arbia Rivel Valley. We make a first stop at the Etruscan hamlet of Murlo, one of the loveliest sites in all of Tuscany. With Montalcino in sight, you will be treated to lunch and wine tasting at a small wine producer and you will learn so much more about Val d’Orcia and Brunello. The next stop is at the Sant’Antimo Abbey, which is a perfect example of romanesque architecture and that is surrounded by olive trees and cypress. The Abbey of Sant'Antimo is a former Benedictine monastery about 5 miles from the Via Francigena, the pilgrim route to Rome. For sure a spiritual site.

In the afternoon we will make time for a stroll in Montalcino. More stunning views!

[fa icon="plus"] Day 5

Sorano - 53 mls - Hilly

We continue our journey through the Val d’Orcia (UNESCO site) but - soon - we enter a less-visited, wilder Tuscany.  We start from San Quirico d’Orcia and our first stop is at the hilltop village of Pienza.  Pienza is known for Pope Pio II, for its perfectly-preserved medieval center, and for pecorino cheese (ready to taste pecorino cheese gelato?). Its hilltop location also affords a stunning view of the valley. We descend and cross the Orcia River. Next is the long climb to the highest point of the whole week: Radicofani mt 814 (2,670 feet). Lunch is planned here. Our final destination is a jump back in time.

The fortress of Sorano is as unique as it is charming and, while intimidating from afar, is also very welcoming to cyclists. 

[fa icon="plus"] Day 6

Saturnia - 50 mls - Hilly

From Sorano we quickly reach Pitigliano. We then cross several small but scenic valleys on the way to Saturnia (the highlight of the day). The site sits over an ancient Etruscan settlement, inarguably the reason they settled there in the first place.    The sulphurous spring water is at a temperature of around 37.5 °C. The main thermal waterfalls are the Mill Falls, located at an old mill as well as the Gorello waterfalls. We take our time here (you should pack a swimming suit and towel). We are about halfway into the ride but you can also ride back in the van if you prefer not to hop back on the saddle. The ride to Sorano is beautiful and climbs a canyon that will suddenly unveil Rocca degli Orsini (or Orsini castle), which dominates the village of Sorano. Dinner is at the hotel.

[fa icon="plus"] Day 7

Maremma and Talamone - 58 mls - Rolling  and flat

Today’s ride heads towards the seacoast and to the charming village of Talamone. We ride among vineyards and open farmland (Sovana and Capalbio production areas) and we take a first stop for lunch in Capalbio, one of the gems that you’ll discover on this bike trip. We soon find ourselves in the coastal Maremma area that is one of the very few territories left in Tuscany that remains true to its wild roots and is untouched by mass tourism. We conclude the ride - and our tour - on the Tyrrhenian Sea. 

Our hotel will spoil us with its terraces overlooking the sea. Pay a visit to Talamone village, which sits on a promontory, before gathering for our final dinner and celebrations at our favorite seafood place. Our final dinner is in the central piazza that honors Garibaldi’s Expedition of the Thousand (they docked in Talamone on the way to Sicily).

[fa icon="plus"] Day 8


After breakfast we say goodbye and your guides will give you a lift to the Florence airport.


What's Included

• Professional tour guides throughout the program 

• All accommodations

• All breakfasts, all lunches (some picnics), and six dinners

• Wine with dinner

• Wine tastings

• Guided tour of Siena

• Support vehicle during the tour and luggage transfer

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

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

• Bike rental (3T Exploro

• GPS navigation and maps (digital) 







Fortezza di Sorano


More Info

Food and Wine

It's often pointed out 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.

Strade Bianche Pro Race

Strade Bianche (formerly Eroica Pro) is organized by RCS Gazzetta dello Sport (same organizers as the Giro d’Italia), and is a  ‘newer’ race in the international pro circuit. However, the fact that it is ridden on the strade bianche unpaved roads has given the race an epic aura that few other races have. Cobblestone and dusty strade bianche wait for the best riders each year on the 1st weekend in March. It starts and ends in Siena.
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.

Libere Terme 

Thermal springs flow endlessly  (ask the Romans) from deep underground and create little paradise bubbles.  Terme di Saturnia belongs to the Libere Terme, which is a circuit of self-governing and free thermal spas.  However, there is a more luxurious option at the spa hotel in town. 


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