Tuscany Cycling Tour

A land of elegance, beauty and dreams

Illustration displaying a cycling tour duration of nine days and eight nights
Illustration displaying eight days of riding on a cycling tour
Illustration displaying a total riding distance of 565 kilometres for our Tuscany cycling tour
Illustration displaying a total riding elevation of 9965 metres for our Tuscany 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.

Three riders cycling through Olive groves and vineyards in Tuscany
A sunset over the rolling Tuscan Hills
Two riders in Montepulciano
Three riders cycling in the Crete Sinese

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: 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 into the amazing landscape of the Crete Senesi and then on to our hilltop villa.

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

A ride profile of a ride to Siena and the val d'Orcia

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: 70km
Elevation: 1455m

A ride profile of a ride to Montalcino

Today is a bit of a ‘rest day’ on the bike as the group heads out on a traditional coffee shop ride after a leisurely start before our long Tuscan lunch later in the day. Expect rolling hills and a undulating landscape that is speckled with small groves of trees and sliced by a maze of narrow country roads.

Highlight: Grain covered open rolling hills of the Val d’Orcia
Distance: 40km
Elevation: 570m

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: 90km
Elevation: 1680m

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: 90km
Elevation: 1410m

A ride profile of a ride into San Gimignano

Pricing & Dates

$6,395.00 AUD per person twin share / Maximum 12 guests

2021

4th to 12th June 2021
$1,995 AUD (deposit)
29th July to 6th August 2021
$1,995 AUD (deposit)
15th to 23rd September 2021
$1,995 AUD (deposit)

2022

3rd to 11th June 2022
$1,995 AUD (deposit)
28th July to 5 August 2022
$1,995 AUD (deposit)
15th to 23rd September 2022
$1,995 AUD (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

While airfare, bike hire and travel insurance are not included in the Tour cost, they can be fully arranged for you. Talk to us when booking.

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.

GPS

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 cycling tour of Tuscany, non-riding partners enjoy a customised travel program, designed to meet their interests and the best experiences Tuscany 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

Accommodation

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

Testimonials

More Inspiration

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