Best of Tuscany Ready to book main pictures
Best of Tuscany Ready to book main pictures

Best of Tuscany Ready to book

A bike ride through purest beauty! This memorable bike tour takes you to the heart of Tuscany, among superfine red wines, olive groves, and hills designed by cypresses, wonderful historic centers, and cheerful locals. Really exciting moments on the bike await you. From the sinuous ups and downs through rolling hills to the exciting passages under the ancient walls of medieval towns. From the vineyards of Brunello d Montalcino and Nobile di Montepulciano to the farmhouses surrounded by olive groves. From the museum cities of Florence and Siena to the legendary places of the Eroica. Prepare your legs and your heart for an unforgettable journey!

| Cycling | Avid | 7days/6nights | 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, Florence and San Gimignano

The amazing towns of Siena, Florence 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 up rideD
2Asciano to MontalcinoCycling 90Km/1800mB
3Montalcino to San GimignanoCycling 100Km/1500mB
4San Gimignano to FlorenceCycling 70Km/1250mB
5Florence to Gaiole in ChiantiCycling 82Km/1740mB
6Gaiole in Chianti to AscianoCycling 70Km/1200mB D

Tour Map

Day 1: Benvenuti in Toscana!

Tour briefing, bike fitting and warm up ride

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 Montalcino

In the land of Nobile di Montepulciano and Brunello di Montalcino wines
Asciano to Montalcino 1453

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 and Pienza, a real model of Renaissance city, we'll get to the medieval village of Montalcino, kingdom of the fine Brunello di Montalcino wine.

Overnight: Montalcino
Included: Breakfast

Day 3: Montalcino to San Gimignano

Towards the towers of medieval Manhattan
Montalcino to San Gimignano 1933

From the Brunello's land to the towers of San Gimignano, one of the best examples of urban architecture, created by the rich Tuscan merchants of the late Middle Ages, known as the ancient Manhattan.

Overnight: San Gimignano
Included: Breakfast

Day 4: San Gimignano to Florence

In the lands of Chianti Classico
San Gimignano to Florence 1983

Between places and settings of the amusing scenes of Boccaccio's Decameron, boundless vineyards in the Chianti Classico, and breathtaking views over the wonderful city of Florence.

Overnight: Firenze
Included: Breakfast

Day 5: Florence to Gaiole in Chianti

Through the Chianti Classico wine-growing area
Florence to Gaiole in Chianti 5759

Today you will cross the legendary territories of Chianti Classico those that, according to the legend of the black rooster, were crossed at dawn at a gallop by the knight of Florence, in the challenge with the city of Siena launched to put an end to the disputes and establish a definitive border between the two rival cities. Today Chianti Classico is the trademark of a wine production specification, undoubtedly one of the most famous in the world, in whose logo the legendary black rooster always stands out. A history spanning over 300 years, which began in 1716, when Cosimo III, the Grand Duke of Tuscany, set the boundaries of the Chianti wine production area. This means that we will go through vineyard and wineries, but in fact not only because there will also be woods and fascinating villages. We are also entering the territories that host the legendary Eroica cycling race, which takes you back to the romantic dusty atmospheres of cycling of the past, made up of little technology, effort and a lot of passion.

Overnight: Gaiole in Chianti
Included: Breakfast

Day 6: Gaiole in Chianti to Asciano

On the legendary roads of the Eroica
Gaiole in Chianti to Asciano 3197

A rich and varied day. You will have the opportunity to try the mythical routes of the Eroica, discover the ancient "Contrade" of Siena, and immerse yourself in the postcard landscapes of the Crete Senesi.

Overnight: Asciano
Included: Breakfast Dinner

Day 7: Departure

Arrivederci Amici!

It’s time to say goodbye, but we know you loved this magical tour in Tuscany and you want to be back in the Med with us!

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!

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.

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.

Villa Nardi
Villa Nardi

Located in a lush park, this beautiful villa combines the peace of the countryside a stone's throw from the wonderful center of Florence.

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:
  6 nights in nice hotels 4*
  6 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 + Ultegra: € 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

This tour is ready to book

Book now or ask for more information
This tour is ready to book