Tuscany “Strade Bianche”


Tuscany “Strade Bianche”

We don’t like Tuscany, too many landscapes, too many cypresses, too many velvety hills, too many vineyards, too much, too much, too much… Too many Tuscany to visit.
We take you to three different areas of Tuscany: Crete di Siena, Towered Cities, and Chianti.
We want you to be thrilled by pedaling the most beautiful gravel roads of Italy, visiting the majestic medieval cities, and enjoying the generous Tuscan cuisine and its red wines.
Tuscany is too demanding, too many roads to ride, too much to see, too much to eat, too much to drink, too much, too much…

At a Glance

6 Days | 5 Nights | 5 Rides
Roads type: 60% Tarmac, 40% Gravel
Bike required: Gravel

Daily Itineraries

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

Regular itinerary:

RIDER LEVEL: Recreative/Intermediate

Total ride distance,  220  miles  (350 km)
Total climbing, 20,700 feet (6.300 m)

Extended itinerary:

RIDER LEVEL: Intermediate/Advanced

Total ride distance, 290 miles  (460 km)
Total climbing, 29,500 feet (9.000 m)

Day by Day agenda

Day 1 –Arrival in Italy, welcome and warm-up ride

Arrival in Italy. We pick you up at Florence Airport (FLR) or at the other pickup point previously agreed.  Approximately two hour van transfer to the heart of Val d’Orcia.     Hotel Check-in , and after a light lunch you have two options, few hours to recover from the fatigues of the trip and relax in the hotel’s or setup and test your bike with a ride with our guides.

Is a bike paradise from the beginning. We pedal the slopes of the Val d’Orcia to Pienza (UNESCO World Heritage Site), the Renaissance city of the Pope.  

When darkness is coming: OSTERIA DEL LEONE

After the welcome aperitif in Italy in the “thermal” square of Bagno Vignoni (it will be a real surprise), you have a dinner at the Osteria del Leone where your culinary journey into regional Tuscan cuisine begins. Well-kept rooms, courteous service, excellent food cooked with a sure and modern hand. Even the cellar will be able to introduce you to the great Tuscan reds, then to bed, tomorrow we start. Overnight in Val d’Orcia.

Regular: 24 miles – 2,600 feet 

Extended: 30 miles – 3,100 feet

Day 2  – Montalcino Vineyards – Eroica Montalcino

It starts to get serious, two beautiful itineraries in the vineyards of “Brunello di Montalcino” where at the end of May the intermediates of historic bicycles challenge each other with the Eroica Montalcino. Gravel roads between the Val d’Arbia, the Crete Senesi and the Val D’Orcia, passing through the wood of Castiglion del Bosco, Argiano Castle, San Angelo in Colle, Sant’Antimo Abbey.

When darkness is coming: OSTERIA LE LOGGE

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. Let’s start from the end: a visit to the cellar, four floors in the basement of the Jewish ghetto in the historic center of the city of Siena, is a must. At the table we enjoy the warm atmosphere, an elegant and territorial cuisine made of high quality raw materials with tasting of the KING of Tuscan red wines: Chianti “Gallo Nero”.

Overnight in Val d’Orcia.

Regular: 27 miles – 2,900 feet

Extended: 36 miles – 4,100 feet

Day 3 – Chianti Vineyards – Eroica Classic – Northern Route

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).  

When darkness is coming: 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. We will dine in an elegant restaurant in the upper part of the city, warm atmosphere, attentive service, revised regional cuisine with excellent quality ingredients, it will be the evening of Vino Nobile tasting.

Overnight in Val d’Orcia.

Regular: 32 miles – 3,050 feet

Extended: 50 miles – 5,050 feet

Day 4 – Sante Marie Hill – Eroica Classic – Southern Routes

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

When darkness is coming: IL CONTE MATTO

Dinner in the medieval village of Trequanda (12th century), after an aperitif at sunset on the terrace overlooking the Crete Senesi, an “all-meat” menu of Chianina beef and Cinta Senese pork are the great protagonists, a sincere journey through flavors Tuscans with the famous “Bistecca alla Fiorentina”, the best Italian preparation of grilled meat. In the cellar rest 300 labels, the best of Tuscany, the small wine producers of Montepulciano await you.

Overnight in Val d’Orcia.

Regular: 48 miles – 3,250 feet

Extended: 64 miles – 5,250 feet

Day 5 – Val d’Orcia, Crete Hills and Montepulciano Vineyards

Today we tours the Val d’Orcia (UNESCO World Heritage Site) , the Renaissance center of Tuscany, a ride through the hills to the vineyards of Montepulciano where the “Nobile” other 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 in the Renaissance.When darkness is coming: BOCCON DIVINOIt 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. In the kitchen the new generation with Alessandra who brought fresh air and it was immediately love. We are in the homeland of Brunello, this is the ideal place to drink the niche products of very small producers. Overnight in Val d’Orcia.

Regular: 38 miles – 3,400 feet

Extended: 44 miles – 4,400 feet

Day 6 – Greetings and see you soon with us on the Italian roads

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

If you come back home, we will take you to Florence (FLR) airport, or if you plan to stay longer to visit Italy, we will be happy to help you.

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

Dinner in the great Italian “Trattoria”

Contrary to popular belief, Italy does not have a single gastronomic tradition (Pizza, Pasta, Cannolo) but many traditions closely linked to their territory, which make up a very interesting mosaic. Our goal is to introduce you to it, to immerse you, every evening we take you to the “Great Italian Trattorias” where the Italian culinary heritage is preserved and perpetuated.
Nella cucina regionale toscana dominano ancora sulla tavola i piatti della cosiddetta cucina povera, la gastronomia che nei secoli si è sviluppata a partire dai pochi ingredienti a disposizione, simbolo di ristrettezza ma anche della capacità di saper trasformare cose semplici e materie prime avanzate in piatti gustosi. Nonostante le sue umili origini, la cucina toscana vanta una serie di prodotti straordinari, tutti da scoprire. Una cucina robusta, dai sapori decisi, dove spicca l’uso di carne (Fiorentina T-Bone), verdure e legumi (Ribollita) e aromi forti (Pici all’Aglione).


The restaurant is housed in the old walls of the village of Trequanda, a suggestive environment with wooden beams and pastel colors, the cuisine that celebrates local meats, “Cinta Senese” and “Chianina”, combined with one of the cellars that we like most more. The restaurant and terrace overlook the hills of the Crete Senesi precipitously, a plus that alone justifies the trip.
Highlights dishes:
Starter: Crunchy artichoke on soft pecorino cheese, mint flavored tomato mustard.
First course: Egg spaghettini creamed with butter and scorzone black truffle from the “Crete Senesi”.
Main course: “Chianina” Breed Scottona Steak and Tuscan White Veal Florentine-style cooking.


We are in Montalcino, home of Brunello, one of the world capitals of red wine. The restaurant is a historic address that bases its success on the skill of Alessandra (in the dining room) and Marina Fiorani (in the kitchen). High-level culinary proposal always in the name of tradition. Very nice place with a breathtaking view of the Val d’Orcia and the Crete Senesi. Obligatory stop!
Highlights dishes:

Starter: Candied egg yolk, sponge and parmesan cheese cream, “Crete Senesi” white truffle.
First course: Tagliatini with basil pesto, river shrimp tartare, lemon and crunchy 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 tavern where in the kitchen Eliana skilfully juggles fresh and local ingredients, many of which are of her own production, to give life to the genuine dishes of the Tuscan tradition. The environment is beautiful: an old house surrounded by nature. It drinks very well.
Highlights dishes:
Starter: Cardoncello mushroom, cream of cannellini beans, sweet gorgonzola sauce.
First course: Rice “Gnudo” (Tuscan gnocchi), Pienza ricotta, spinach, brown egg, tomato water.
Main course: Cheek peposo (tuscany stew with pepper) and mashed potatoes.


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: 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.

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Living in the Charme

We have selected some beautiful boutique hotel, historical house or vinery house, where you will enjoy to stay in relax 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 avoid the commitment of transfers and 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

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Whats is included


  • 5 night in Historical Mansions, 4* Luxury Hotels or Villas located in special places
  • All gratuities at hotels and restaurants
  • Concierge & suggestion service for additional vacation ticketing, booking


  • Guest pick-up / drop-off in airport or other meeting point
  • All-vacation long, guests, bikes and luggage transport


  • 5 daily breakfasts in hotel
  • 5 lunches during the riding time
  • 5 social hours aperitivo
  • 5 dinners in 5 different GREAT ITALIAN TRATTORIA with the best Italian regional wines


  • 5 riding days,  2 daily itineraries with different grade of effort
  • 2 expert local certified guides multilingual will ride with you and support all day
  • 1 professional mechanic with support/SAG Van during the tour
  • Energy bars and sports drink during pedaling
  • Daily bike maintenance and daily laundry service for bike clothing
  • GPX daily tours documentation
  • Custom Hirides.com cycling kit


  • Professional guides for visits to the tour cities, experts for visits to wineries and support in all not pedaling activities as described in the tour program
  • Wine tasting/oil tasting at the producers’ premises. Visits to dairies with demonstration of cheese making, as described in the tour program


  • Rental of professional bicycle (e-bike or muscle) or transport of your beloved bicycle in Italy


  • Civil Liability Insurance and Italian health insurance for non European citizens

What is not included or on-demand


  • Through our partners we can organize the flight for you (ON-DEMAND)


  • Meals, transportation, hotel costs or expenses in the days before and after the tour


  • Staff Hirides.com gratuities is not included


  • Travel Protection Plan not included, but heavily suggested


  • Luggage service, before/after tour days (ON-DEMAND)
  • Bike transport service, before/after tour days (ON-DEMAND)


  • Regional cuisine cooking class
  • White Truffle tasting
  • White Truffle hunting


  • Cost of passport and visas
  • Personal expenses while on the vacation
  • Personal transportations when not included on the Tour
  • Beverages not specifically agree/included
  • Additional hotel expenses, mini-bar, wellness treatments
  • Optional activities not scheduled by Hirides.com
  • All not explicitly declared in the vacation description