Tuscany Wine & Bike Tour
Harvest in Chianti vineyard landscape
View of the medieval town of Montalcino
View of Siena Cathedral dome and medieval city rooftops through autumn leaves in Tuscany, Italy.
Cityscape of Florence with Duomo dome, Palazzo Vecchio tower, and river under blue sky.
Pienza town on a hilltop overlooking rolling Tuscan fields under a bright blue sky.
Two glasses of red wine and charcuterie on a stone surface in Tuscany at sunset
Mountain biking on a dirt road toward Montepulciano in Tuscany at sunset.
Crete Senesi landscape
Castello di Brolio (Castle of Brolio), Tuscany
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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

We offer road cycling, trekking cycling and mountain biking holidays.


Our road cycling holidays are suitable for avid road cycling enthusiasts whose endurance is high enough to withstand multiple long cycling days in a row.


Our trekking cycling holidays are suitable for anyone, as the stages are short enough for most people, and the terrain is not technical — mostly tarmac and gravel. They will still be enjoyed most by people who cycle occasionally and feel comfortable with multiple days in a row on the saddle and some moderate climbing. For those looking for more leisurely cycling holidays, we offer an e-bike option.


Our e-MTB holidays are suitable for most people comfortable on a mountain bike who are fine with some rougher gravel roads and steeper hills, made easier with electric assistance. However, the single trails MTB holidays are suitable mostly for avid mountain bikers, as they tackle technical trails and fast descents, but are very adjustable to your skills and style of riding.

On our guided tours, you will have professional local guides. Our guides will make sure that you will have expert guidance combined with great fun and a memorable experience.

We are always looking for the perfect fit for you. We use a few different accommodation providers that fit our standards but they are subjected to availability, especially in the high season. We can also adjust the holiday, keeping in mind your preferences and budget and can always find a more suitable solution for your taste.

We recommend booking as early as possible. Most of our tours run through very touristy places where accommodation is limited. Most of the great places start getting booked for summer before spring.

It really depends on the level of your restriction. Vegetarian options are fairly easy to find in Europe, but vegan dishes, on the other hand, are extremely hard to come by in rural areas and in smaller towns. Please note that the places where we stop for lunch are often traditional and may have difficulties accommodating you outside of their standard menu. We suggest you keep this in mind.

If you want to, sure! We are well aware that some people love to stay in groups while others prefer some more alone time on their trip. We wanted to give you the opportunity to do things your way. It is your holiday, after all! As long as you respect the group timings and locations designated by your guide, please feel free to customize your itinerary and create your own adventure!

Most of the tours can be done even in light rain, as long as you dress accordingly. It is not unusual in the summer that there are afternoon thunderstorms, so early starts are advisable. If the weather looks really bad, we will try to adjust the tour or skip a stage with a shuttle.

The best time for cycling in Europe varies depending on your preferences and the region you’re targeting. Spring offers moderate temperatures and scenic blooms in Southern Europe, while early summer is ideal for enjoying the mild climate and extended daylight in Northern Europe. Late summer to early fall in Central Europe is perfect for those who prefer cooler temperatures but still want to enjoy plenty of daylight. For winter escapes, consider warmer regions like the Canary Islands or Tenerife.

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.

from 2.450 € /person
Experience Europe like never before with Cycling Holidays Europe. From scenic routes to cultural gems, discover the ultimate cycling vacations on two wheels.

Have questions? Talk to us.

Lan Lajovic
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