Tuscany Bike Tours

Strade Bianche

Tuscany is a dream brought to life—a land of breathtaking landscapes, iconic cypress trees, rolling velvet hills, and world-renowned vineyards.
Join us on an unforgettable cycling journey through three stunning regions: the impressive Crete di Siena, the charming Towered Cities, and the enchanting Chianti wine country.
Feel the thrill of pedaling along Italy’s most scenic gravel roads, immerse yourself in the rich history of medieval towns, and indulge in the authentic flavors of Tuscany’s legendary cuisine and exquisite red wines.

This isn’t just a bike tour—it’s the ultimate Tuscan adventure!

At a glance

  • 6 Days | 5 Nights | 5 Rides

  • Roads type: 60% Gravel – 40% Tarmac

  • Bike required: e-Gravel

Daily itineraries

2 different itineraries to chose from every day.
You are free to mix them to create your personal vacation.

Regular itinerary: Suitable for RECREATIONAL LEVEL cyclists

Total distance: 129 miles (211 km)
Total climb:  13,170 feet (4,015 m)

Extended itinerary: Suitable for ENTHUSIAST LEVEL cyclists

Total distance: 181 miles (290 km)
Total climb:  18,700 feet (5,700 m)

Daily itineraries

Arrival in Italy. We pick you up at Florence Airport (FLR).  It’s approximately a three hour van transfer to the heart of Vald’Orcia. Upon hotel check-in and a light lunch you have two options: free time to relax at the hotel or bike setup to go for a ride and explore the area.

It’s a biker’s paradise right from the start. We pedal the slopes of the Val d’Orcia to Pienza (a UNESCO World Heritage Site), the Renaissance city of the Pope.
Then we descend to the Cappella della Vitaleta one of the most famous shooting spots in Tuscany.

At sunset OSTERIA DEL LEONE welcomes you to an aperitivo.

After the welcome aperitif at Bagno Vignoni a 16th century village (it will be a real surprise), you will dine at Osteria del Leone where your culinary and wine journey into regional Tuscan cuisine begins. Well-kept rooms, courteous service, excellent food cooked with a sure and modern hand. Overnight stay in Val d’Orcia.

Regular itinerary for RECREATIONAL LEVEL cyclist: Total distance 15 miles (24 km) and Total climb 1,480 feet (450 m).
Extended itinerary for ENTHUSIAST LEVEL cyclist: Total distance 19 miles (30 km) and Total climb 1,840 feet (560 m).

It’s getting serious, two beautiful itineraries in the vineyards of “Brunello di Montalcino” where at the end of May the intermediates of the historic bicycles challenge each other with the Eroica Montalcino. Dirt roads between the Val d’Arbia, the Crete Senesi and the Val D’Orcia, passing through the Castello di Argiano, San Angelo in Colle, Abbazia di Sant’Antimo and the most beautiful Brunello vineyards.

At sunset OSTERIA LE LOGGE welcomes you to an aperitivo.

After visiting the city of Siena, we have dinner in the most beautiful trattorias in the city, a stone’s throw from Piazza del Campo. A visit to the cellar in the Jewish ghetto and part of the historical center of the city of Siena, is a must. At the table we enjoy a special regional cuisine in a warm and elegant atmosphere. We invite you to taste the King of Tuscan red wines: Chianti “Gallo Nero”. Overnight stay in Val d’Orcia.

Standard itinerary for the RECREATIONAL LEVEL cyclist: Total distance 22 miles (36 km) and Total climb 2,820 feet (860 m).
Extended itinerary for the ENTHUSIAST LEVEL cyclist: Total distance 34 miles (54 km) and Total climb 4,180 feet (1,270 m)

We are in the Chianti area. It’s a change of views, but with equal satisfaction in riding these dirt roads made famous by the vintage bike event Eroica in Gaiole, a long ride on the ridge of the Chiantishire hills.

The route passes through the villages which names you can read on the labels of the best bottles of Chianti wine: Panzano in Chianti, Fonterutoli, Radda in Chianti, Gaiole in Chianti…only to name a few.

At Sunset: LE LOGGE DEL VIGNOLA

We are at dinner in Montepulciano, an ancient Etruscan city (4th century) whose current fame is given by Vino Nobile, one of the great Tuscan reds. It will also be an evening of the Vino Nobile tasting. We will dine in an elegant restaurant in the upper part of the city with a warm atmosphere, attentive service, re-interpreted regional cuisine and excellent quality ingredients. Overnight stay in Val d’Orcia.

Standard itinerary for the  RECREATIONAL LEVEL cyclist: Total distance 32 miles (52 km) and Total climb 3,050 feet (930 m).
Extended itinerary for the ENTHUSIAST LEVEL cyclist: Total distance 47 miles (75 km) and Total climb 4,790 feet (1,460 m).

Today we leave the Chianti vineyard area to ride the southern loop of the Eroica. The route is mostly on gravel roads across Crete Senesi. We ride through the nicest villages of Tuscany, Lucignano (IMHO) and we climb the hills of Sante Marie and the ascent dedicated to Fabian Cancellara where the “Strade Bianche” races are often decided.

At sunset: IL CONTE MATTO

Dine in the medieval village of Trequanda (12th century), after an aperitif at sunset on the terrace overlooking Crete Senesi. Chianina beef and Cinta Senese pork are the great protagonists. Immerse yourself in a journey of Tuscan flavors with the famous “Bistecca alla Fiorentina”, the best Italian preparation of grilled meat. The cellar houses over 300 of the best Tuscan wines. The small wine producers of Montepulciano await you… Overnight stay in Val d’Orcia.

Standard itinerary for the RECREATIONAL LEVEL cyclist: Total distance 31 miles (50 km) and Total climb 2,770 feet (845 m).
Extended itinerary for the ENTHUSIAST LEVEL cyclist: Total distance 44 miles (71 km) and Total climb 3,970 feet (1,210 m).

Today we tour Val d’Orcia (UNESCO World Heritage Site) , the Renaissance center of Tuscany and ride through the hills to the vineyards of Montepulciano where the “Nobile” another red wine from Tuscany is produced. In addition to the vineyards we will cross the large open spaces of the «Crete». We will pass by two small fortified and perched villages where it seems that time stands still.

At sunset: BOCCON DIVINO

It has been “The Trattoria” in Montalcino, since 1992. A gem set in a postcard view, where you can taste tried and tested recipes that never betray their territorial roots. We are in the homeland of Brunello and it’s the ideal place to drink the niche products of very small winemakers. Overnight stay in Val d’Orcia.

Standard itinerary for the RECREATIONAL LEVEL cyclist: Total distance 29 miles (49 km) and Total climb 3,050 feet (930 m).
Extended itinerary for the ENTHUSIAST LEVEL cyclist: Total distance 37 miles (60 km) and Total climb 3,950 feet (1,200 m).

After breakfast, it’s time to say goodbye and start the journey back home.

If you are returning home, we will accompany you to Florence Airport (FLR).
If you plan to continue your stay in Italy, we will be happy to assist you.

We hope to see you soon on one of our next tours on the roads of Italy !

Tours Calendar

Daily Experiences

The bike tours we have prepared will keep you busy from morning to early afternoon. Once  you return to the hotel you can choose whether to wait for dinner time in complete relaxation, or follow your guides to some interesting experiences that they have prepared for you.
Every day they are committed to offer you a unique experience, you will surely love!

Piazza del Campo: a surprise at first sight.
The Basilica of San Domanico: a historical gothic church which preserves the remains of Saint Catherine.
Via Francigena: a fundamental pilgrimage route in the history of the city where the most important buildings and monuments can be found: Palazzo Monte dei Paschi, Palazzo Tolomei, Palazzo Chigi Saracini.
Cathedral of the Assumption: a jewel of gothic architecture and treasure chest containing the famous works of Michelangelo, Donatello and Bernini.

An extraordinary 16th century hill top village that rests on the rolling hills of Siena like a natural balcony.
Montepulciano has Etruscan and Roman origins that developed in the Middle Ages and then acquired all its beauty during the Renaissance. It is an open-air set where several of the most famous movies have been filmed: The English Patient (1996), The Twilight Saga, New Moon (2009).
In addition to a guided tour of the city, you can take a “gourmet tour”,  including tasting the Nobile and Rosso di Montepulciano wines and enjoy a walk through the alleys of the historic center that lead to discovering the village and its history.

Pienza, the “Ideal Fortressed City” built by Pope Pius II (1458), which dominates Val d’Orcia (a UNESCO World Heritage Site since 2004). Let’s start the visit: The proportions of Piazza Pio II embody that sense of harmony sought in the Renaissance. The square is home to the main cathedral and Palazzo Piccolomini with access to the city walls.
The Cathedral dominates Piazza Pio II with a beautiful white stone façade. Different styles coexist here: the 3 naves recall German churches, the façade recalls Florentine infuence and there are also Gothic elements. The Bastions: Pienza was a fortified city with mighty bastions that now offer the opportunity to take a wonderful walk to admire a breathtaking view of Orcia.

Brunello di Montalcino is a Tuscan red wine, produced in the Montalcino area and is considered one of the longest-lived Italian red wines.
Officially “born” in 1869, it is obtained from a single type of grape: Sangiovese da Brunello.
It is undoubtedly one of the best red wines in the world and the best productions/vintages are admired by enthusiasts from all over the world.
Start with a tour of the vineyards followed by a tasing in a historical vat wine cellar starting from the younger Rosso di Montalcino  and then some Brunellos from different vineyards and vintages.

Dining in the great Italian “Trattoria”

Contrary to popular belief, Italy does not have a single gastronomic tradition like pizza, pasta and cannoli, but many traditions closely linked to their territory, which make up a very interesting mosaic. Our goal is to introduce you to it, and to immerse you in this culinary experiance.

Every evening we take you to the “Great Italian Trattorias” where the Italian culinary heritage is preserved and celebrated. We take you to the most beautiful valley in the Dolomites, Val Badia, one of the “Ladin” valleys where the population speaks German and where you may find traditional cuisine.

Alternatively you can explore the tastes of Ladin and South Tyrolean cuisine which has its roots in Austrian cuisine. Even with obvious differences, the two cuisines are a mix of unmistakable flavors, aromas and spicy and smoked hints that enrich many of the local specialties. Here the harsh climate inspires a generous gastronomy with sweet and savory flavors.

The restaurant is housed in the old walls of the village of Trequanda, a suggestive environment with wooden beams and pastel colors. The cuisine celebrates local meats, “Cinta Senese” and “Chianina”, combined with one of the cellars that we like the most. The restaurant and terrace overlook the hills of the Crete Senesi, a plus that alone justifies the trip.
Specialty Dishes:
Starter: Crispy artichokes on soft pecorino cheese with a mint flavored tomato mustard.
Pasta and Risotto: Egg spaghettini with creamed butter and “scorzone” black truffle from “Crete Senesi”.
Main course: “Chianina” Scottona Steak and Tuscan grilled Veal Florentine.

We are in Montalcino, home of Brunello, one of the world capitals of red wine. This historical  restaurant bases its success on the skills of Alessandra and Marina Fiorani. They offer high-level traditional culinary cusine in a very nice place with breathtaking views of  Val d’Orcia and Crete Senesi. It’s a must!
Specialties dishes:

Starter: Candied egg with a foamed Parmigiano Reggiano cheese cream and “Crete Senesi” white truffle.
Pasta and Risotto: Tagliatini with basil pesto and river shrimp tartare, served with crispy lemon infused polenta.
Main course: Local rabbit in porchetta stuffed with spinach and taggiasca olives, almonds, capers and thyme zucchini.

The seasons mark the times of this former tavern where in the kitchen Eliana skillfully combines fresh and local ingredients, many of which are of her own production, to give life to the genuine dishes of the Tuscan tradition. Enjoy your meal in a beautiful environment surrounded by nature.
Specialties dishes:
Starter: Cardoncello mushrooms, creamed cannellini beans and sweet gorgonzola sauce.
Pasta and Risotto: Rice “Gnudo” (Tuscan gnocchi), Pienza ricotta and spinach.
Main course: Cheek peposo (tuscany stew with pepper) and mashed potatoes.

One of the most beautiful late medieval villages in all of Tuscany and home of the “Nobile di Montepulciano” red wine, it hosts this elegant restaurant. Recently revised both in the welcome and in the culinary offer, it offers a high quality service to its international clientele. Local traditional dishes and excellent bottles of “Nobile di Montepulciano” await us.
Highlights dishes
:
Starter: Montalcino-style tripe with saffron, “Cinta Senese” sausage and pecorino cheese,
First course: Risotto Carnaroli grand reserve with garlic, creamed goat cheese and anchovies.
Main course: Seared pigeon with seasonal side dish and chilli mustard.

A stone’s throw from Piazza del Campo there is a place where time has been deliberately stopped with the aim of bringing guests back to Siena as it was. On the contrary, in the kitchen the perspective is the future one, with the great local culinary school which keeps the identity intact, but opens it towards new sensory horizons. Do not miss the 4-storey cellar in the basement.
Highlights dishes:

Starter: Marinated anchovies, vanilla, raspberries, rocket pesto.
First course: Handmade tagliatelle, Tuscan ragout.
Main course: “Priest’s hat” (type of beef), garden vegetables, beef garum.

In one of the most beautiful late medieval villages in all of Tuscany and home of the “Nobile di Montepulciano” red wine, it hosts this elegant restaurant. Recently revised both in the welcome and in the culinary offer, it offers a high quality service to its international clientele. Local traditional dishes and excellent bottles of “Nobile di Montepulciano” await us.
Highlights dishes:

Starter: Liver pâté, coffee bread, spiced pear and cooked wine sauce.
First course: Pici traditional pasta, black garlic, Pientino cheese, crumbs with bread, thyme, pepper.
Main course: Chamomile lamb with heirloom mustard, popcorn crust, pickled vegetables.

Living in the Charme

We have selected some beautiful hotels, historical houses and vineyard houses, where you will enjoy to stay in the total relaxation after your bike experience.
Most of them have SPA treatment available in a charming exclusive environment.
Our tours involve staying in a single hotel for the entire holiday, to have more time to immerse yourself in the culture of the area.

The discreet charm of the Tuscan countryside, in the relaxing atmosphere of one of the most fascinating places in Italy, our Hotel Relais awaits you in Val d’Orcia. Be our guest in an historical 16th century mansion.

In the small medieval village of San Quirico, in the heart of the Val d’Orcia, Capitano Collection with its Luxury & Design Boutique hotels, villas, palaces and historic dwellings, within and outside the walls of the small village few steps from each other, boats suites and rooms all different and highly charaterized, to let every guests find his most suitable dimension

* All breakfasts, lunches, dinners
* One certified regional guide for every 8 guests, one bike mechanic and one SAG van driver
* Snacks, sport drinks, beverages, energy bars during the tour
* 2 different itineraries every day with different experience levels
* Guest pick-up / drop-off to and from the airport or other meeting point
* Daily bike maintenance and cleaning
* Daily laundry service for bike gear
* Custom Hirides.com cycling kit: bib shorts, jersey and socks
* Private guided tours at museums, historical sites, wineries and other select attractions as noted in the Travel Planner
* All gratuities at hotels and restaurants
* Special events, including wine tastings and other select attractions as mentioned in the Travel Planner
* Professional bicycle rental (e-bike or muscle) or transport of your beloved bicycle to Italy
* Baggage transfers, handling and assistance
* Civil Liability Insurance and Italian health insurance for non European citizens

  • Guide gratuities
  • Ttransportation to and from your HiRides trip start & end locations
  • On-your-own meals & activities
  • Additional cycling kit
  • Travel Protection Plan (highly recomended).

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