Tuscany Bike tour around Siena and Chianti


An unforgettable tour in the Italian region where many people coming from abroad for a visit have choosen to remain forever, enchanted by its sweet hilly landscapes, by its art treasures, by the refinement of its culture, its great wines and its delightful, country cuisine. This route conducts you through extraordinary valleys and territories like Val d’Elsa, Chianti (very famous for its wines), Val d’Arno, Val d’Orcia, Crete senesi, via Francigena (ancient route used for pilgrimages), among thick vineyards and wonderful hills.

Type of tour: Self-guided
Min/max people: from 2 pax
Length of stay: 8 days/ 7 nights
Arrival/Departure: Siena/Siena
Tour level: Medium/ easy – Total length 120/130 km
Dates 2019: Every day from 1st of March till 15th of October




  • Bike among spectacular vineyards, hills and ancient villages
  • Be enchanted by the spectacular hundred towers of San Gimignano
  • Step back in time while touring Volterra – an ancient and perfectly preserved medieval village on the top of a hill surrounded by a memorable landscape
  • Enjoy Siena, with its marvellous Piazza del Campo, where since many centuries the famous “Palio” takes place, its typical cathedral and the narrow medieval roads
  • Discover Chianti region and the Tuscan countryside cycling along minor roads in a continuous sweet ups and downs
  • Uncover the Orcia Valley, still wild and authentic with its small jewels as Pienza – the perfect Renaissance town and Montalcino.
  • Take your time to taste full-bodied red wines and genuine Tuscan food in the most authentic part of Tuscany


Day 1: Siena

Arrival and accommodation in hotel in Siena. Time at disposal to discover the town by your own. Overnight.

At the hotel you will find the informative material, road maps and detailed description of the itinerary.

The bikes will be delivered to your hotel in the evening.

Day 2: Siena – Castle of Brolio – Castelnuovo Berardenga – Asciano (km 49)

After breakfast, departure for the bike tour.

Today you will cycle among Chianti hills with its wine and woods. Take your time to visit Brolio Castle, the hamlet of Villa a Sesta, the town of Asciano .

Arrival in Asciano and accommodation. Overnight.

Day 3:  Asciano – Monte Oliveto – San Giovanni d’Asso – Pienza (km 52)

Breakfast and departure by bike. Today you will bike from Chianti to the wild Orcia Valley.

Today you will see the monastery of Monte Oliveto, the medieval town of San Giovanni d’Asso, the monastery of Sant’Anna in Camprena and Pienza, the jewel city of the Renaissance.

Arrival in Pienza and accommodation. Overnight.

Day 4: Pienza – S.Quirico – Montalcino – Buonconvento – Murlo (km 56)

Breakfast and departure by bike. Today you will continue discovering the Orcia Valley – famous for its renowned red wine Brunello di Montalcino.

Don’t’ miss a walk in the historical center of San Quirico, a glass of Brunello in the town of Montalcino, and to take a picture in the medieval hamlet of Murlo.

Arrival in Murlo and accommodation. Overnight.

Day 5: Murlo – Monteriggioni – Colle Val d’Elsa (km 64)

Breakfast and departure by bike.

Passing through Radi and Sovicille, you will reach the walls of Monteriggioni – a real jewel incredibibly well -preserved and the historic center of Colle Val d’Elsa.

Arrival in Colle Val d’Elsa and accommodation. Overnight.

Day 6: Colle Val d’Elsa – Casole d’Elsa – Ulignano – Volterra (km 47)

Breakfast and departure. Today you will bike among the beautiful hills of Chianti Senese and visiting the ancient villages of Casole d’Elsa and Volterra.

Arrival in Volterra and accommodation. Overnight.

Day 7: Volterra – Il Castagno – San Gimignano – Certaldo- Siena (km 47)

Breakfast and departure by bike. Arrival in San Gimignano – the city of the hundred towers. Take your time for a walk in the historic centre where you will find artisan shops, wine cellars, food producers. Here you can stop for lunch and taste local cuts and the white wine Vernaccia di San Gimignano.

Proceed your journey and get to the historic center of Certaldo.

Arrival and transfer by evening regional train to Siena. Arrival and accommodation. Overnight.

Day 8: Siena

Breakfast. Check out and departure.

We suggest an extension to Florence and Cinque Terre. The tour is available also as 5 days version.

Price per person:  965 euro

The tour includes:

  • Accommodation in 3* hotels and a 4* hotel in Pienza
  • Breakfast Buffet
  • Luggage transfer from hotel to hotel
  • Road book, maps, tourist information in English
  • Telephone service hotline

The tour does not include:

  • Transfer from origin to starting point and return
  • Meals and beverages
  • Entrance fees to churches, museums and so on
  • Tips and personal expenses
  • Everything not listed under item “the tour includes”

Extras and Supplements:

  • Single room € 230
  • High season (July, September & October) € 50
  • Rental bike (21 speed bike with free wheel) + 1 pannier bag and 1 tool kit € 150
  • Rental E-bike € 260
  • Helmet € 10

Additional information:

Typical landscape of the Tuscan countryside is the hill: the routes are almost always wavy,

with easy ups and downs; only sometimes you find some steep slopes. Medium-easy, the

route is predominantly asphalted; the dirty routes are in good conditions, there are 5 – 15 km

of dirty road every day

Tour level medium/easy

Km 120/130

Bicycle city bike

Luggage transfer yes

On request Additional nights, transfers from /to Florence, Rome, Pisa