Tuscany Cycling Tour

A land of elegance, beauty and dreams

Illustration displaying seven days of riding on a cycling tour
Mountain Illustration displaying a cycling tour difficulty rating of eight out of ten

An overview of our cycling holidays in Tuscany

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.

Two riders in Montepulciano

Tuscany Cycling Tour Ride Itinerary

Welcome to our Tuscany Bike Tour

You’ll enjoy daily rides through the superb Tuscan countryside, taking in the densely forested hills of Chianti, the open rolling hills of the Val d’Orcia and the magical countryside of the San Gimignano province. Post ride on our cycling tours of Tuscany, we’ll enjoy free time in the mid to late afternoons, making the most of the stunning places 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: 35.9km
Elevation: 719m

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: 89.6km
Elevation: 1601m

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 traverse through some of the most iconic vlilages between Siena and Florence.

Highlight: The free flowing descents that follow the 5 climbs.
Distance: 75km
Elevation: 1733m

A ride profile of a ride to Greve in Chianti

Today’s ride will take in three distinct climbs as you get to see first hand the truly majestic Val d’Orcia that was included as a UNESCO World Cultural Landscape in 2004, on your way to the mesmerising Montalcino, home of the sensational Brunello d Montalcino.

Highlight: Riding through the ancient hilltop town of Montalcino
Distance: 82.6km
Elevation: 1662m

A ride profile of a ride to Montalcino

Today you set off in the direction of Umbria, in true L’Eroica style you take to the ancient Roman roads (affectionately
known as the Strade Bianche) as you traverse through this postcard perfect landscape and pretty villages, before reaching one of Tuscany’s prettiest towns, Montelpuciano.

Highlight: The open rolling hills of the Val d’Orcia
Distance: 67.2km
Elevation: 1354m

A ride profile of a ride in the crete Sinese

Your longest day, setting off in the direction of Umbria and traversing through a picture-postcard landscape through tiny villages, before reaching one of Tuscany’s prettiest towns, Montepulciano.

Highlight: The quiet and open landscape around Montepulciano
Distance: 68.1km
Elevation: 1286m

A ride profile of a ride in the Val d'Orcia

This is a truly typical Tuscan day on the bike where you will encounter undulating quiet country roads amidst the rolling hills, woods, olive groves and vineyards as you wind your way from the Val d’Orcia to what many consider is the most beautiful part of Tuscany,

Highlight: The final kilometres with vista of San Gimignano and its 16 towers in the distance.
Distance: 105.3km
Elevation: 1631m

A ride profile of a ride into San Gimignano

Pricing & Dates

per person twin share / Maximum 14 guests

Show Price As


9th to 16th June 2025
1995 (deposit)
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: Santa Maria Novella Train Station, Florence
Pick Up Time: 11:00am

Finish Location & Details

City: Florence, Italy
Drop Off Location: Santa Maria Novella Train Station, 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

Two piece italian made cycling kit

Ride Kit

Not Included

Have More Questions About Our Tuscany Cycling Tour?

See our FAQs page for answers to common questions.

Bike Hire & Gear

Carbon Road Bike with Electronic Shifting

You can choose to hire a Wilier Cento 10SL carbon road bike with Sram Rival Etap, a compact crankset, with a 32 rear cassette & disc brakes.

Carbon Road Bike with Mechanical Shifting

You can choose to hire a Bianchi Sprint with mechanical Shimano Ultegra groupset, a compact crankset, with a 32 rear cassette & disc brakes.

Non-Riding Partners

As part of our cycling tour of Tuscany, non-riding partners enjoy an active and dedicated travel program, designed to deliver a diverse range of activities and the best experiences Tuscany has to offer. Whether its guided walks in the hills of Chianti and the Val d’Orcia, visits to beautiful castles and hilltop towns, meet the producer experiences or cooking classes, non-riding partners experience the beauty and uniqueness of each area we visit. With an itinerary curated by Nancy and delivered together with a range of partners and guides whom she personally selects, It’s sure to be a holiday in Tuscany you’ll never forget.

As our non-riding partner program is an active adventure, there is a minimum walking requirement for non-riding guests for each tour. Please enquire when booking

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 selection of boutique hotels and family-run villas across Tuscany which reflect the true character of Tuscany and its 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

Scroll to Top