Many Faces of Tuscany Bike Tour

Many faces of Tuscany

History, Towers, Woods, Vineyards, Small Villages, and Landscapes.

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

Roads type: 60% Tarmac, 40% Gravel
Bike required: Gravel


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,  170  miles  (275 km)
Total climbing, 15,350 feet  (4.600 mt)

Extended itinerary:

RIDER LEVEL: Intermediate/Advanced

Total ride distance, 220 miles  (360 km)
Total climbing, 22,000 feet  (6.700 mt)

Tour Description: Some of many faces of Tuscan routes

6 Days | 5 Nights | 5 Rides

Tour Details

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 Routes

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 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. 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.