Classic Tuscany Ready to book main pictures
Classic Tuscany Ready to book main pictures

Classic Tuscany Ready to book

Immerse yourself in the purest beauty! This memorable bicycle trip takes you to the heart of Tuscany, among superfine red wines, olive groves, and hills designed by cypresses, wonderful historic centers, and cheerful locals. You will ride from the Crete Senesi to the lands of the Vino Nobile di Montepulciano and Brunello di Montalcino, passing the "ideal city" of Pienza. Then the medieval atmosphere of Siena and San Gimignano will welcome you, and finally, the Chianti Classico and the romantic routes of the Eroica will close your wonderful journey.

| Cycling | Active | 8days/7nights | Self-Guided | From € 1470 |


Brunello di Montalcino, Nobile di Montepulciano and Chianti wines

Brunello di Montalcino, Nobile di Montepulciano and Chianti wines

The amazing towns of Siena and San Gimignano

The amazing towns of Siena and San Gimignano

The Crete Senesi landscape

The Crete Senesi landscape

The Eroica routes

The Eroica routes

Day to Day

B: Breakfast; L: Lunch; D: Dinner;
1Benvenuti in Toscana.Warm upD
2Asciano to PienzaCycling 50Km/1098mB
3Pienza to MontalcinoCycling 43Km/890mB
4Montalcino to SienaCycling 55Km/850mB
5Siena to San GimignanoCycling 60Km/950mB
6San Gimignano to Gaiole in ChiantiCycling 54Km/1100mB
7Gaiole in Chianti to AscianoCycling 40Km/600mB D

Tour Map

Day 1: Benvenuti in Toscana.

Tour briefing, bike fitting and warm up ride
Benvenuti in Toscana. 6992

Arrival in Tuscany, shuttle or individual arrival at our accommodation in Asciano countryside. Tour explanation, delivery of tour documentation, and careful bike fitting, then possibly warm up ride to the pretty medieval town of Serre di Rapolano.

Overnight: Asciano
Included: Dinner

Day 2: Asciano to Pienza

Across the beautiful villages of Montepulciano and Pienza
Asciano to Pienza 5240

Today we ride through the Val d’Orcia, a quintessential Tuscan landscape, made out of rolling hills dotted with cypress trees; its landscape is listed as a UNESCO World Heritage Site. After the marvelous Montepulciano we end in the pretty Pienza, a real model of Renaissance city.

Overnight: Pienza
Included: Breakfast

Day 3: Pienza to Montalcino

In the land of the Brunello di Montalcino wine
Pienza to Montalcino 1100

From the romantic Renaissance atmosphere of Pienza, heading towards the medieval village of Montalcino, kingdom of the fine Brunello di Montalcino wine. Along the way the beautiful Orcia valley and the majestic Sant’Antimo Romanic abbey.

Overnight: Montalcino
Included: Breakfast

Day 4: Montalcino to Siena

From the vineyards of Montalcino to the rolling hills of Siena
Montalcino to Siena 4815

A beautiful ride from the vineyards of Montalcino to the rolling Crete Senesi, until the lively but still authentic Siena, the most medieval town of Tuscany.

Overnight: Siena
Included: Breakfast

Day 5: Siena to San Gimignano

Across the Val d'Elsa up to the Manhattan of Medieval times
Siena to San Gimignano 1075

We leave Siena along the Via Francigena route, after the medieval walls of Monteriggioni we continue through the hills around the Val d'Elsa. The ride ends among the high towers of San Gimignano.

Overnight: San Gimignano
Included: Breakfast

Day 6: San Gimignano to Gaiole in Chianti

An Epic day along the Eroica roads
San Gimignano to Gaiole in Chianti 4130

We say goodbye to the unique skyline of San Gimignano then enter the Chianti Classico region, where we will experience some of the dirt roads that have made the Eroica famous all over the world, the iconic vintage bike ride through the Chianti region.

Overnight: Gaiole in Chianti
Included: Breakfast

Day 7: Gaiole in Chianti to Asciano

At the origins of Chianti Classico wine
Gaiole in Chianti to Asciano 8663

We go through the Chianti wine region, discovering the stunning Brolio Castle, a true symbol of the territory, because the official method for the production of Chianti wine was established here in 1872. Then we pass through the ancient thermal baths of Rapolano before ending our day in the countryside of Asciano, chez our friends Elisa and Alessandro.

Overnight: Asciano
Included: Breakfast Dinner

Day 8: Arrivederci!

Well, it’s time to say goodbye, but we are sure this part of Italy will touch your hearts and you’ll come again to visit more!

Included: Breakfast

The accomodations

Il Molinello Agriturismo - Asciano
Il Molinello Agriturismo - Asciano

Il Molinello is a cozy accommodation in the rolling hills east of Siena, better known as the Crete Senesi. Alessandro and Elisa produce high-quality extra virgin olive oil. If you want a super local experience, this is definitely the place!

Hotel Corsignano - Pienza
Hotel Corsignano - Pienza

Beautiful, functional and, above all, ecological. This is our comfortable 4-star hotel, set in the frame of Tuscany’s most beautiful and unspoilt area, reaching from Pienza to the Orcia-Valley, passing along the colorful roads you have always dreamed of.

Dei Capitani Hotel
Dei Capitani Hotel

In this ancient building, you can breathe the typical atmosphere of an ancient Tuscan village. The property offers a large garden with a swimming pool overlooking the valley of the vineyards where the fine Brunello is produced.

Italia Hotel, Siena
Italia Hotel, Siena

Few steps away from the north gate of the old town, completely renovated, “comfort inclusive” rooms, super breakfast. Italia hotel is your house in Siena.

Bel Soggiorno Hotel
Bel Soggiorno Hotel
San Gimignano

Cozy accommodation in a typical 14th-century building, with a perfect location in the heart of the ancient town, to discover the magic and charm of San Gimignano on foot.

Badia a Coldibuono
Badia a Coldibuono
Gaiole in Chianti

A villa that was previously a monastery, situated in an expansive landscape, rich in symbolism and at the same time, quiet and intimate.


You can bring your own bike or rent one from us, we offer great bikes from selected Italian and international brands: road bikes, leisure cycling, mountain bikes, e-bikes, all in perfect working conditions. You can book your bike on the Booking / Information form.

Price and Supplements

Tour Price: € 1470 per person
Deposit: 30%, Balance: 30 days before departure

This price includes:
  7 nights in nice hotels 4*
  7 breakfast and 2 dinners
  Welcome meeting and tour briefing
  Maps, route notes or GPS tracks
  Luggage transportation inn2inn
  Telephone assistance
  Peace of mind being with our experienced team

This price not includes:
  Local Taxes (approx. 10 €)
  Drinks at Dinner

Road Bike Carbon + Ultegra: € 220

E-Road Bike Carbon + Ultegra: € 400

Road Bike - Flat Bar Carbon + 105/Sora: € 200

Touring Bike: € 110

High season supplement: € 250 (Jun 26 - Sep 04)

Single room supplement: € 250

Solo Traveller: € 450


Free cancellation for any reason till 30 days before departure.
Free cancellation for COVID-19 related reasons till 10 days before departure.

Self Guided Tour

This means you will pedal free at your pace following maps and tracks received during our pre tour briefing at your arrival. We will advise you where to have lunch and dinner, about sightseeings along the road and where to find technical assistance. You can start on any day of the year.

With just 4 people, this tour can be ride as a Guided Tour

In our Guided tours you have:

  • A cycling guide riding with you showing his region
  • Van support with water, electrolytes and snacks, available if you want to skip the hardest climbs
  • A daily picnic lunch featuring local and fresh products
  • Dinners at hotel or restaurants featuring traditional food
  • Shuttles from arrival airport and to departure airport
Ask for a quote and Go Guided

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