Dinner at a Tuscan restaurant in Florence













Tuscany Wine & Bike Tour
7 days / 6 nights
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Starting point
Florence
Finish point
Siena
Fitness level
4/5
Season
From May to October
Starting point
Florence
Finish point
Siena
Fitness level
4/5
Season
From May to October
Highlights
- Explore Florence’s historic centre and enjoy a welcome dinner
- Pedal through Chianti’s vineyard-scapes, passing Greve, Castellina, and Radda
- Cycle across mixed terrain – paved and gravel – through the Crete Senesi
- Enjoy two curated wine tastings: Chianti Classico and Brunello di Montalcino
- Traverse Val d’Orcia’s cypress-lined ridges and terraced slopes
- Conclude your journey in Siena, surrounded by centuries of art and history
What’s included in the price?
Self-guided
NOT INCLUDED
OPTIONAL EXTRAS
Join a deeply immersive journey through Tuscany with this Wine & Bike tour tailored for travellers who want to combine the exploration of the Tuscan landscapes and culinary delights with cycling!
From your arrival in Florence—with its striking dome, historic bridges over the Arno, and your included dinner at a traditional trattoria paired with a fine Tuscan red—you’ll find yourself anchored in the heart of one of Italy’s most vibrant regions.
You’ll cycle through the vineyard-lined slopes of Chianti, through quiet side-roads and shifting surfaces of asphalt and gravel, arriving in villages like Greve, Castellina, and Radda, where the wine culture is tangible.
Two standout wine tastings are included: one evening in the Chianti Classico zone, another in the Brunello-centred heart of Montalcino, giving you the chance to slow down, sip, and see what these hallowed names really mean.
You’ll ride through the lunar clay hills of Crete Senesi and then to the open fields and cypress-lined ridges of Val d’Orcia—both landscapes recognised for their breathtaking quality and heritage.
The cycling routes won’t push you into athlete mode: you’ll ride steadily, with time to enjoy the countryside, olive groves, vineyard rows, and historic hill-town architecture.
The finale in Siena (a UNESCO-listed city with its famed Piazza del Campo and medieval skyline) will bring you home to culture and comfort.
This tour is for those who want to travel at the intersection of motion, heritage, and wine—pedalling by day, indulging by night, and discovering Tuscany in a layered, memorable way.
Frequently Asked Questions
All available guidance options
Self-guided
Those who like good adventure and limitless flexibility should go on a self-guided cycling holiday. It offers complete freedom, multiple detour opportunities, and exploration at your own pace without having to adapt to a group.
Hassle-Free
We handle itineraries, accommodations, and anything else you prefer not to deal with, so you can enjoy carefree walking holidays.
Trusted by many
We are a financially protected company, fully bonded and insured, keeping your money safe and allowing you to travel with confidence.
Handpicked Adventures
Only the best hut to hut hikes in Europe, cherry-picked by our local team with an in-depth knowledge of the region.
Unbeatable support
Our 24/7 customer support is where we show our passion, bringing you a better experience by making your well-being our number one priority.













































