Make it memorable with Bike’n wine!

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Discover Tuscany Tour

Discover Tuscany Tour

$4950 $3960 per person

Make memories that will last a lifetime

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Bike and e-Bike rental

Cooking Class

Wine Making and Tasting

Olive Oil Tasting

PRICE: $3,960 per person based on double occupancy ($800 supplement for single room occupancy)

DEPARTURE DATES: Choose your date from April 1st to October 15th, 2020

DURATION: 5 Nights / 6 Days

LEVEL: Beginner (road bike) – Easy (e-bike)

Tuscany offers an ideal scenario for cycling enthusiasts of all levels, from amateur cyclists to anyone just wishing to pedal calmly while enjoying the beauty of the region. Tuscany is typically a hilly region. For cycling fans, this means pushing yourself on the same hills many cycling legends trained, including Bartali, Cipollini and Bettini. Tuscany is in fact a land of cyclists and wherever you choose to go pedal you’re likely to cross paths with many two-wheel aficionados.

From the agriturismo where you will stay, you’ll ride in the world heritage Val d’Orcia, in the lunar landscape of Crete Senesi, among the vineyards of Chianti and Montalcino; you’ll walk along the corridors where the Chianti wine was “invented”, you’ll stroll in beautiful towns such as Siena and Pienza.

On this tour, you will experience the best of Tuscan life, visiting a local winery, learning more about food recipes and wines, discovering the people and the culture behind your food and “simply” being immersed in the quiet Tuscan countryside.


Our central location allows for 6 spectacular rides in 6 different areas of Siena Province (Chianti Classico, Crete Senesi, Val d’Orcia, Val di Chiana, Val d’Arbia, Siena town)

An authentic experience with a Tuscan family (3 generations)

Accommodations in a restored XIVth century mill

Visit farms and wine cellars and discover the people behind your food

Breakfasts and dinners inspired by the short supply chain (km 0): all the products are farm fresh organic, from the surroundings areas or Slow Food Presidia.

Wine and extra-virgin olive oil tasting course

Relax at the SPA and thermal Springs in Rapolano Terme


Bike rental - Focus Cayo 515 or e-bike (supplement for De Rosa Di2 electronic shifting $100)

Personal guides with van and mechanic support

6 nights in a beautiful Agriturismo/ resort where you will stay for the entire duration of the trip. No need to pack every day and change hotels

All meals during your stay- breakfast, on-the-road lunches, and dinners

Wine tasting and educational tour

Olive oil tasting course

Cooking lesson with Elisa. Visit and tasting at 2 wine estates

Guided tour of Siena, a beautiful medieval town surrounded by walls

Bike ' n Wine cycling uniform

This tour does not have transfer to and from the airport

6 Nights / 7 Days
  • Departure
  • Included
    4 Star Accommodation
  • Not Included
    5 Star Accommodation
    Star Accomodation
    Transfer to and from the airport

Day 1

Distance: 30 km – 16 miles
Terrain: a few rolling hills


Our optional group shuttle will depart Terontola train station at 11:30 am and will take you to the agriturismo in Asciano (35 minute ride). We will get together at 12:30 pm in the Enoteca located inside the agriturismo for lunch and a brief introduction. In the afternoon, after the bike fitting, we will ride around Asciano (with an optional extra loop) and stop for an artisan gelato! Dinner at agriturismo.

Day 2

Distance: 52 km – 42 miles
Terrain: moderate with one good climb


Today we ride along the Val di Chiana reaching Fattoria Santa Vittoria for a truly rustic, historical and organic atmosphere. The Val di Chiana is a huge fertile flat, bordering Lazio, Umbria and Tuscany. It is famous for the production of excellent products such as olive oil and wine. Many villages dot the surrounding hills with their unique heritage of art and history left from the Etruscans, Romans, and during the Renaissance period. From the moment you enter Fattoria Santa Vittoria you’ll feel as if you have stepped back in time. You will have the opportunity to visit the wine cellar and taste a gourmet lunch along side with wine tasting. Later in the afternoon, once back at the agriturismo, you will also gain more knowledge on olive oil with a olive oil tasting course. Extra virgin olive oil is not only a must on the Tuscan table, it is also pride and joy to Tuscans!

Day 3

Distance: 76 km – 48 miles
Terrain: rolling hills


Today we will plunge into Val d’Orcia, considered one of Italy’s wonders by UNESCO which describer the region as: “It is the exceptional testimony of the way in which the landscape has been reshaped in the course of the Renaissance to mirror the ideals of the good government and to create at the same time an aesthetically pleasing eye-catcher…”

Medieval castles, sunny rolling hills, isolated hilltop towns, charming isolated rural homes, avenues of cypresses, rows of vineyards, olive groves, and golden wheat fields are just some of the elements of the fantastic and harmonious landscapes of Valdorcia! We will stop in Pienza strolling in town and have lunch in a typical Osteria. Pienza is widely known as the “ideal city of the Renaissance”, the creation of the great humanist Enea Silvio Piccolomini who later became Pope Pius II. Piccolomini had the money and influence to transform his birthplace village, the humble Corsignano, into what he considered the Utopian city should be, exemplifying the principles and philosophy of classical times and of the great Italian Renaissance. Thus, Pienza became the realization of a dream! Pienza, on the list of world heritage sites of UNESCO, is famous not only for its beauty, art, historical monuments but also for its Pecorino cheese. Walking around the streets you will be able to taste and smell this delicious and inimitable product.

Later in the afternoon once back at the agriturismo you will have an evening to learn to taste the “Nectar of the Gods” , a wine tasting course to discover together with Alessandro (sommelier A.I.S.) the main DOCG produced in the province of Siena: visual, olfactory and gustative analysis, coupling food and wine.

Dinner during the wine tasting course

Day 4

Distance: 48 km – 30 miles
Terrain: rolling hills


Today is a rest day! There is an optional loop ride along the Crete Senesi, the world’s most photographed panorama! . A wide sea of clay spreads out over the countryside: one evocative, soft hill follows the other, the few forests leave space to the endless stretches of wheat fields and grassland, able to change their colours with the succession of the seasons.

For those who don’t want to ride there will be a morning at the Spa and natural hot spring San Giovanni in Rapolano Terme. Hot springs are naturally produced by the emergence of geothermally heated groundwater from the Earth’s crust (The waters flow from the spring at a temperature of 102° Fahrenheit) The springs of Rapolano, were known in the Etruscan and Roman eras for the properties of their healing waters. The Terme di San Giovanni are a natural terrace overlooking the sea of hills that is the Crete Senesi, so while relaxing in the pools or having lunch you can enjoy a breath taking view on this lunar landscape. After a lunch at the Terme di San Giovanni there will be a shuttle to Siena. Siena is an intimate, sleepy place with honey-stoned medieval streets. Siena hasn’t changed in appearances from the middle age to nowadays and walking through its streets it’s a kind of travel in time, the search of a golden age. The historic city is listed as a world heritage site by UNESCO. Piazza del Campo is the heart of the town and is the home to the famous summer horse-race, known as il Palio. After a guided visit of Siena, you’ll be able to walk around and have dinner in town.

Day 5

Distance: 74 km – 46 miles
Terrain: rolling hills


Today we ride through the famous Chianti Classico region.

According to recent statistics the word “Chianti” is, on all continents and at all latitudes, a synonym for Tuscany. There’s indeed no travel lover on this planet who has not heard about the famous Tuscan hills yet, where the most renowned red wine is produced: the Chianti, which we can easily recognize by its characteristic label of the black rooster (gallo nero). For modern travellers “Chianti” is not only a geographic indication but also a word that describes a certain lifestyle, sober and elegant, a harsh and evocative landscape made of forests, vineyards and olive groves, a land that has given birth to famous personages, a land where every village is a little masterwork of architecture: from Greve to Panzano, from Castellina to Gaiole, from Radda to San Casciano, from Castelnuovo Berardegna to Vagliali.

This territory is indeed very homogeneous regarding its history, its traditions, feelings and its cooking. But the Chianti is also a territory which is rich in culture, that can be discovered step by step wandering the little streets and exploring the numerous villages, castles and abbeys that are hidden behind every corner.

Castello di Brolio is the destination of our ride: Brolio was built about AD 1000 and owned by the monks of the Badia Fiorentina; the “new” owners, the Ricasoli family, have been in possession since 1141. Bettino Ricasoli (1809–80), the so-called Iron Baron, was one of the founders of modern Italy, and is said to have invented the original formula for Chianti wine.

We will stop in Gaiole in Chianti to stroll in town and have lunch.

How about learning to make pasta from scratch or learning a little about Tuscan cuisine?

At the end of the cooking lesson, of course, you will taste, during a nice dinner, what you prepared!

Day 6

Distance: 83km – 52 miles
Terrain: rolling with one good climb


Our last ride, your last challenge, will lead you to Montalcino, the city of the famous wine Brunello di Montalcino DOCG. We will ride along the Pecorile road (the ancient road used by shepherds for the transhumance of the herds from the mountains of the Casentino Valley to the plains of Maremma) in the heart of Crete Senesi and the Asso Valley. Montalcinois a classic fairytale hilltop town, set within a full circle of fortified walls and watched over by a mighty castle of medieval perfection. Montalcino, renowned all over the world for the production of its precious Brunello red wine, has scarcely changed in appearance since the 16th century. Once you get up to the town, a magnificent spectacle unfolds for your eyes: rolling sunny hills dotted with yellow and red flowers, ancient oak trees, picturesque olive groves, scenic country roads winding through perfect vineyards and isolated cypress trees atop hills. The town has been made incredibly rich and famous by its Brunello wine, one of the world’s best and most appreciated Italian wines. Montalcino was already well-known for its fine red wines during the 15th century. However, the precious formula of the fantastic Brunello was invented in 1888 by Ferruccio Biondi Santi, who first had the idea of leaving out the grapes used in the traditional Chianti recipe, such as Canaiolo and Colorino, and using only the Sangiovese variety. Montalcino is not just wine, it is also very rich in artistic treasures. The historical center is dominated by the mighty and imposing Rocca or fortress built in 1361 to mark the passage of Montalcino under the domination of Siena. The views from its ramparts are spectacular, stretching towards Monte Amiata, across the Crete to Siena, and across all of the Valdorcia and the hills of Maremma. We will have a picnic lunch at Giuditta Parisi’s farmhouse Nostra Vita, where the Parisis produce Brunello di Montalcino DOCG. Annibale and Giuditta will lead you in a different world, made out of love for nature, art, philosophy and of course good traditional wine. Nothing at Nostra Vita is a result of mass!

Farewell dinner.

Day 7


After breakfast at 9 am we offer a 35-min group shuttle to Terontola train station from where you can connect to Florence in 1 hour and a half and to Rome in 2 hours.
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