Tuscany Wine & Bike Tour
Harvest in Chianti vineyard landscape
View of the medieval town of Montalcino
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Tuscany Wine & Bike Tour

7 days / 6 nights

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Cycle from Florence to Siena through the wine regions of Chianti and Montalcino, combining scenic rides, vineyard landscapes, and evening wine tastings.

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

6 nights in 3-4* hotels with breakfast
Dinner at a Tuscan restaurant in Florence
2 wine tasting experiences in Castellina and Montalcino
Digital guidebook with detailed itinerary and route instructions
GPS navigation with an easy-to-use app
Tour design and organization
Service and support during your tour
Luggage transfer

NOT INCLUDED

Tourist tax

OPTIONAL EXTRAS

Airport transfer
E-bike
E-road bike
Gravel bike
Hotel upgrades
MTB
Regular bike
Road bike
Single supplement

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

Our priority is to find the ideal accommodation that suits your needs. We collaborate with several lodging providers that meet our criteria, but please note that availability can be limited, particularly during peak seasons. Furthermore, we can tailor your holiday to align with your preferences and budget, and are committed to finding a more suitable alternative that matches your taste.

Our tours are categorized into three difficulty levels: leisurely, moderate, and challenging. Although each may include both easier and more demanding days, our rating system reflects the average difficulty level for a typical day.


Leisurely tours take place primarily on flat, paved cycling paths, asphalt roads, or easy gravel tracks, and they are suitable for all fitness levels.


Moderate tours may include some uphill climbs or technically more demanding terrain, but they are manageable for individuals of average fitness.


Challenging tours entail either long distances and numerous climbs or technical terrain, possibly featuring downhill sections requiring proficiency with a mountain bike.

Our tours can be adapted to any bike type, whether road, gravel, or mountain bike. We are in constant communication with you to find the optimal conditions for your cycling holidays in Italy.


The most versatile option is a gravel bike, even if you are coming on a road cycling holiday. It does not really affect your road performance while allowing you to take some scenic backroads that can be in a slightly worse state than the main ones. A gravel bike is usually more comfortable as well.

If you are not bringing your own bike and equipment, we can certainly arrange that for you. We have a wide selection of bikes at our disposal and we will choose the ones that best fit your tour. All we need from you is your usual bike size and any other relevant information or preferences so we can make sure you will be comfortable throughout your trip.

The availability of food options in Italy depends on the extent of your dietary restrictions. While it is relatively easy to find vegetarian dishes, locating vegan meals can be challenging, particularly in smaller towns and rural areas. Additionally, the traditional lunch stops we make may have limited ability to accommodate special requests beyond their standard menu. We recommend considering this when planning your meals.

Absolutely, the choice is yours! We understand that some travelers enjoy group activities while others prefer a more solitary experience. Therefore, we want to offer you the flexibility to personalize your trip to suit your preferences. After all, it is your holiday! As long as you adhere to the designated group timings and locations outlined by your guide, please feel free to customize your itinerary and embark on your own adventure.


If you want to have a completely independent holiday, you can always opt for a self-guided tour, which is possible on most of our tours!

The optimal time for our tours varies depending on the specific trip. However, typically late spring (May) and early autumn (September) are ideal. Of course, summer is also an excellent time to travel. Additionally, some of our holidays can be enjoyed in winter too!

With proper attire, most of our tours can still be enjoyed even in light rain. During the summer months, afternoon thunderstorms are not uncommon, so it’s recommended to start your day early. If inclement weather is forecasted, we will do our best to modify the tour or arrange for shuttle transportation to skip a particular stage.

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 take care of route planning, accommodations, luggage transfers, and all logistics, so you can focus purely on enjoying your ride.

Tried & Tested Adventures

Our cycling routes are hand-picked & tested, to ensure breathtaking landscapes, smooth roads, and maximum safety - giving you the perfect ride every day.

Unbeatable Support

Our 24/7 customer support is where we show our passion, ensuring your cycling holiday runs smoothly and your well-being is always our top priority.

Book with Confidence

We are a financially protected company, fully bonded and insured, keeping your money safe and allowing you to travel with confidence.

from 2.450 € /person
Discover Italy on two wheels with our cycling holidays! Choose from a variety of available cycling tours in Italy's most beautiful and picturesque regions.

Have questions? Talk to us.

Lan Lajovic
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