Chianti Uncovered Cycling Tour

A land of elegance, beauty and dreams

Six days of cycli9ng graphic
Mountain Illustration displaying a cycling tour difficulty rating of six out of ten

An overview of our cycling holidays in Chianti

Tuscany a land of beauty, elegance and dreams. Where the colours of the landscape and the flavours of the traditional cuisine change with the seasons, and the slow rhythm of life is felt with each encounter, ride and meal.

To the cyclist who ventures into this world, it is heaven. Urged by a sense of adventure and the discovery of magnificent views at every turn, you can expect long, warm days on our Tuscany cycling tours surrounded by incredible panoramic views of rolling hills, olive groves, vineyards and medieval hilltop towns, all while embracing the winding roads, challenging climbs and exhilarating descents.

Rediscover your taste for adventure on our Tuscany cycling holiday as you pedal along quiet country roads and cobblestoned streets, enjoying the history, culture and of course the cuisine of this spectacular region.

Tuscany is where our journey began and a place we invite you to share with us as we create a truly authentic experience of our favourite areas to ride and eat in this ancient land, where the art of living is represented through tradition, generosity and talent.

Come ride, eat and drink like a Tuscan. You’re in for an unforgettable adventure.

Three riders cycling through Olive groves and vineyards in Tuscany

Chianti Uncovered Ride Itinerary

Welcome to our Chianti Uncovered Bike Tour

You’ll enjoy daily rides through the superb Chianti countryside, taking in the densely forested hills and slopes dotted with olive groves and endless rows of vines. Post ride on our cycling tours of Chianti, we’ll enjoy free time in the mid to late afternoons, making the most of the stunning place we stay.

Following our welcome lunch, today’s ride to a hilltop hamlet is the perfect introduction to Chianti with the idyllic rolling hills striped with vineyards and backed by dense wooded forests and the little villages that dot the landscape.

Highlight: The picturesque hilltop hamlet
Distance: 50km
Elevation: 890m

A ride profile a beautiful ride around Gaiole in Chianti

It’s time for you to explore on our bicycle tour of Tuscany the sensational cypress lined backroads of Chianti, made famous by its wine, beautiful winding descents and climbs with incredible panoramic views.

Highlight: The winding descent from Radda in Chianti
Distance: 70km
Elevation: 1010m


A ride profile of a ride to Castellina in Chianti

Today you explore the beauty and challenge of the Chianti hills, with the ride including more sustained climbing with 5 distinct climbs as we travese through some of the most iconic vlilages between Siena and Florence.

Highlight: The free flowing descents that follow the 5 climbs.
Distance: 70km
Elevation: 1530m

A ride profile of a ride to Greve in Chianti

Today on our cycling tour of Tuscany, you’ll track south along part of the permanent L’Eroica route on your way to the campo in the centre of Siena. We’ll have a coffee and take in the view before we roll through the amazing landscape of the Crete Senesi.

Highlight: The dry clay hills and spare lunar-like landscape of the Crete Senesi
Distance: 85km
Elevation: 1420m

Today’s ride will take in the spectacular ancient hilltop towns of San Donato and Castellina before visit to the Chianti Sculpture Park.

Highlight: Lunch in beautiful walled town of Monteriggioni. 
Distance: 83km
Elevation: 1495m

Today is an undulating tour through the vineyards and olive groves packed with free flowing descents as we meander through the southern part of Chianti.

Highlight: Views of Siena in the distance from the vine laden hills.
Distance: 64km
Elevation: 1110m

Pricing & Dates

per person twin share / Maximum 12 guests

Show Price As


24th to 30th April 2022



29th June to 5th July 2023


25th to 31st July 2023


Want to enjoy cycling in Tuscany, Italy, on your very own tour? Ask us about a privately run tour for your group.
A map of Tuscany

Start Location & Details

City: Florence, Italy
Pick Up Location: Peretola Airport, Florence
Pick Up Time: 11:00am

Finish Location & Details

City: Florence, Italy
Drop Off Location: Peretola Airport, Florence
Drop Off Time: 11:30am

Inclusions & Details

A sensational antipasto to start a long Tuscan lunch

Accommodation & Meals

A rider getting their hire bike adjusted on a Italian cycling holiday

Ride Support

Brunello di Montalcino tasting

Transfers & Activities

Not Included

Have More Questions About Our Tuscany Cycling Tour?

See our FAQs page for answers to common questions.

Bike Hire & Gear

Full Carbon Road Bikes

You can choose to hire a Pinarello or Bianchi  with a compact crankset.


You can choose to hire a Pinarello e-bike with a compact crankset and a little more power.


An easy to use GPS is provided for your use for the duration of the tour with our daily rides pre installed.

Non-Riding Partners

As part of our Chianti Uncovered cycling tour, non-riding partners enjoy a customised travel program, designed to meet their interests and the best experiences Chianti has to offer. Whether its guided walks, visits to beautiful castles and hilltop towns, guided sightseeing tours or cooking classes, Nancy personally hosts non-riding guests each day with a select range of activities to suit the group.

Non riding partners on a walking tour of Siena
A man painting Tuscan ceramics
The gardens at the Piccolomini palace and the Tuscan landscape in the distance
Walking through the beautiful town of Pienza
Aperitivo time Tuscan style
Non Riding partners hiking in the tuscan countryside


Enjoy our hand-picked family-run villas in Gaiole in Chianti, which reflect the true character of Tuscany and the beautiful, warm and open people with whom we’ll share our experience.

A room furnished in the Tuscan style
The gardens at our Tuscan accommodation
A Tuscan styled bedroom
a pool and stone house in the tuscan countryside
A Tuscan room with a view
An alfresco dinner tuscan style

Food & Wine

Enjoy with us the distinctly different areas of Tuscany and their varied recipes and wines.

The lure of the Tuscan table is immense; characterised by its close association with the land, Tuscan cuisine is earthy, simple in style, and reflective of the region’s changing seasons. We will take you on a food safari of Tuscany that takes in all the very best it has to offer from simple organic produce, grown on our host properties, to exquisite gastronomic dishes at a selection of family-run osterias and restaurants.

Seasonal Tuscan produce
Delicious Tuscan antipasto
A Tuscan Grilliata
Cooking on charcoal Tuscan style
Local made Tuscan produce
A beautiful dessert to finish a long Tuscan lunch


More Inspiration

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