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7-Day Bike Tour through Tuscany

Self-Guided
Book now

Cycling in Tuscany

Discover all that Tuscany has to offer by bike, with the people who know it best.

Enjoy a true cycling adventure in Tuscany with this 7-day Bike Tour, experiencing the rolling hills and medieval hill towns. You’ll cycle through the paradise of the Tuscan countryside and explore the region, including the Val d’Orcia, Pienza, Montalcino and Chianti.
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Programme

On the first part of the week you will cycle surrounded by the beautiful landscape of Val d’Orcia, UNESCO protected site, and you can visit some nice towns including Pienza, Montepulciano and Montalcino.

On the second part you will cycle through the Crete Senesi region to Siena and the Chianti region, famous for its wine. The tour will finish in Florence, where you can add more days to visit this beautiful city.
The Tuscany bike tour is a perfect mix of bike, history, and local product for an unforgettable bike holiday.
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Bike Rental

This tour is organised in close cooperation with a local bike rental company. They have selected the best roads to discover Tuscany by bike, alternating the uncontaminated nature of backroads with beautiful medieval villages, food and wine, nice lodging to stay in and relax at the end of the day.

You can customize this tour with any type of bike that you like. Our partner has a wide range of top quality bikes: hybrid bikes, MTB, electric bikes, E-bikes, gravel bikes or road bikes.
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  • In short
  • Itinerary
<
>
Duration: 7 Days/6 Nights
Level: Active ride
Where: Val d'Orcia - Crete Senesi - Chianti
When: from March to November
Type of terrain: 100% paved (Gravel roads on request)
Day 1 - Benvenuti in Toscana
Individual arrival in Siena, after 2 pm private transfer to San Quirico d’Orcia.

Briefing, dinner on your own and accommodation at Hotel Casanova.
Hotel 4 stars available on request with extra price.
***
Day 2 - Val d'Orcia region
56 km – Elevation gain: 910 meters

The landscapes of Val d'Orcia region, one of the most beautiful place in Tuscany and UNESCO world heritage site.
Visit of Pienza, the "ideal" city of the Renaissance time, also famous for its Pecorino cheese.
A quick stop at Montepulciano, with its winding streets and squares.
Monticchiello, a small medieval and charming town.
Bagno Vignoni, cute medieval town where the main square of the village is a big thermal pool which contains the original source of thermal water.
Take a relax break from the cycling journey and enjoy the SPA before dinner.

Dinner on your own and accommodation at Hotel Casanova. 4 stars hotel available on request with extra price.
***
Day 3 - Montalcino and Brunello region
54 km – Elevation gain: 1180 meters

Long climb direction Castiglione d’Orcia, the beautiful landscapes will compensate the challenging ascent. Stop in the town center and discover the Rocca di Tentennano
Up and down to reach the Brunello region and Sant’Antimo Abbey, the route will take you right in front this beautiful Abbey.
The Abbey of Sant’Antimo, one of the most beautiful romanic church in Tuscany.
Enjoy a Brunello wine tasting in one of the wineries along the route.
Town center of Montalcino, a perfect place for lunch. Suggested Enoteca Alle Logge di Piazza, located in the central square.
Back to San Quirico riding direction Torrenieri.

Dinner on your own and accommodation at Hotel Casanova. Hotel 4 stars available on request with extra charge.
***
Day 4 - Crete Senesi and Siena
57 km – elevation gain: 890 meters

An unforgettable ride surrounded by the beautiful views of the Crete Senesi to the edge of Chianti wine region.
Crete Senesi, where Calanchi and biancane alternate in this suggestive territory.
Passage from San Giovanni d’Asso, the center of the white truffle of the Crete Senesi.
Discover Asciano, small villages with nice churches, streets and square. We suggest to eat something and refill the water bottles before the next part of the stage.
For the photography lovers, you’ll ride very slow this segment…The Via Lauretana offer unique landscapes and you’ll stop many times to take photos.
Siena at the horizon, the visit of this beautiful city will make unique your experience in Tuscany.

Dinner on your own and accommodation in 3 stars hotel located very close the city center of Siena. Hote 4 stars available on request with extra price.
***
Day 5 - Chianti region
58 km - elevation gain: 1160 meters

Leave the city center of Siena riding along the old streets and the road SP408.
Ride through Castelnuovo Berardenga, small village located south of Chianti area.
Villa a Sesta, very nice village with beautiful views over the vineyards.
Possible Climb up to Castello di Brolio on gravel, the view from the Castle is amazing! Before to ride the second part of the tour you will have the opportunity to visit the Castle, dating back to the 11th century and owned by the Ricasoli family since 1141. Take a break at the Agribar, taste the famous Chianti Classico at Enoteca di Brolio.
Gaiole in Chianti, town where L’Eroica vintage race was born.
Radda in Chianti, you’ll cross this beautiful village with the bikes.

Dinner on your own and accommodation at Palazzo Leopoldo.
***
Day 6 - Panzano e Greve in Chianti
53 km - elevation gain: 660 meters

Stage completely set in the Chianti Fiorentino.
Panzano in Chianti, the village became very popular in the last years for its butcher Dario Cecchini, famous for the Fiorentina steak!
The triangular square of Greve in Chianti, with the archied loggias that line its three side. Greve has developed around this piazza over the last 500 years. In the southernmost corner stands the church of Santa Croce, home to several interesting works of art by the Fra Angelico school. Under the arched loggia, you will find numerous stores selling wine, ceramics, artisan products and all kinds of local food
Discover the surrounded of Florence and Impruneta, small village a few kilometers outside the city center.
Riding the last kilometers with Florence at the horizon.
Triumphant arrival at Florence’s Piazzale Michelangelo, last highlights of the Tuscany bike tour.

Dinner on your own and accommodation in 3 stars hotel located at Florence.
Hotel 4 stars available on request with extra price.
***
Day 7 - Arrivederci Toscana
Check-out and individual departure.
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Dates

From March to November

Price from € 1180,- p.p.

For 7 days based on occupancy 2 persons per room

Including:
  • 6 Nights with breakfast in double room
  • Baggage transportation between the hotels 
  • Informations for your daily stage
  • Maps with altimetry of each stage in PDF file
  • GPX tracks for GPS system or mobile App.
  • Private transfer from Siena to San Quirico d'Orcia on day 1
  • Phone assistance by our local supplier

Exclusive:
  • supplement single room
  • contribution to the STO Garant guarantee scheme € 15
  • Tourist city tax
  • Medical insurance

Optional services:
  • Medical insurance
  • Bike rental (Trekking, road bike, Gravel or e-bike)
  • Van support along the route
  • Expert bike guide
  • GPS rental
Book now
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This offer is covered by the STO Garant guarantee. You can find the conditions for this guarantee scheme on STO Garant’s website (www.sto-garant.nl/en/downloads).

Transport

You can come with your own car, by train or by plane. The nearest airports are Pisa and Florence.
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Plant trees for a green and healthy world
Plant trees for a green and healthy world
© 2025 Triptoscana
  • Home
  • Stay
    • Vakantiehuizen
    • B&B
    • Luxe Villa's
  • Arrangementen
    • Kookreizen >
      • Koken in Toscane
      • Kookreis op maat
    • Luxe arrangement in Villa Petriolo
    • Pakketreizen voor- en najaar >
      • Pakketreis Wine & Food
      • Pakketreis Kunst & Cultuur
      • Pakketreis Strand & SPA
    • 5-daagse Bike Tour van Florence naar Siena
    • 7-daagse Bike Tour door Toscane
    • Olijfpluk arrangement
    • Thermen & spa
    • Schildervakantie Toscane
  • Experience
  • Auto huren
  • Treinen naar Florence
  • Webshop
  • Blog
  • Contact
    • Onze service
    • Over ons
    • Recensies
    • Nieuwsbrief
  • Home
  • Stay
    • Holiday homes
    • B&B
    • Luxury Villas
  • Package deals
    • Cooking Tours >
      • Cooking in Tuscany
      • Tailor-made cooking tour
    • Luxury package at Villa Petriolo
    • Spring and Autumn Holidays >
      • Wine & Food Holiday
      • Art & Culture Holiday
      • Beach & SPA Holiday
    • 5-Day Bike Tour from Florence to Siena
    • 7-Day Bike Tour through Tuscany
    • Picking olives package
    • Thermae & spa
    • Painting Holiday in Tuscany
  • Experience
  • Rent a car
  • Contact
    • Our services
    • About us
    • Reviews
    • Newsletter
  • Startseite
  • Ihr Aufenthalt
    • Ferienhäuser
    • B&B
    • Luxusvillen
  • Pauschalangebote
    • Kochreisen >
      • Kochen in der Toskana
      • Individuelle Kochtour
    • Luxuspaket in der Villa Petriolo
    • Frühling und Herbst in der Toskana >
      • Wein & Speisen Urlaub
      • Kunst & Kultur Urlaub
      • Strand- und Wellnessurlaub
    • 5-tägige Radtour von Florenz nach Siena
    • 7-tägige Radtour durch die Toskana
    • Olivenernte-Paket
    • Therme und Spa
    • Malkurs in der Toskana
  • Erlebnisse
  • Autovermietung
  • Kontakt
    • Unsere Dienstleistungen
    • Über uns
    • Bewertungen
    • Newsletter