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Tuscany Cycling Tour

A land of elegance, beauty and dreams

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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.

tuscany cycling tours

bike tours in tuscany

Cyclists riding through Tuscany town centre

Group of cyclists riding on the road to Tuscany while on holiday

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

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

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

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

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

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

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

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

Pricing & Dates

$5,995.00 AUD per person twin share / Maximum 12 guests


4th to 12th June 2021 $1,995 AUD (deposit)
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29th July to 6th August 2021 $1,995 AUD (deposit)
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15th to 23rd September 2021 $1,995 AUD (deposit)
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3rd to 11th June 2022 $1,995 AUD (deposit)
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28th July to 5 August 2022 $1,995 AUD (deposit)
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15th to 23rd September 2022 $1,995 AUD (deposit)
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Want to enjoy our bike tour of Tuscany as a privately run tour for your group?
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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

Accommodation & Meals

  • Our Tuscany cycling tours include 8 nights’ accommodation, twin share with your own private bathroom.

  • Single occupancy available. Talk to us when booking.
  • All breakfasts and dinners at a range of our favourite restaurants, osteria’s and home cooked locations, including nightly aperitivo hour and local wines and beers at each dinner.

Ride Support

  • Professional bilingual ride guides with extensive cycling experience, local knowledge and first aid experience, ensuring your riding experiences are truly local and take in many of the undiscovered back roads and rolling hills of this spectacular and diverse region.
  • Unique routes, available on our GPS and provided as part of our bike tours in Tuscany.
  • Support van on daily rides, with mechanical support and your safety as our priority.
  • Nutritious energy snacks and hydration are provided

Transfers & Activities

  • All transfers / transportation from pick up to drop off, including baggage and bike transportation.
  • Wine tastings and activities as outlined in the detailed tour itinerary.
  • Entrance fees to sites, museums and all other non riding activities.

Ride Kit

  • 2 piece, Italian made A’QTO Cycling Kit including jersey and bib shorts.
  • Laundry for your cycling clothing.

Not Included

  • Airfare.
  • Bike hire.
  • Travel insurance.
  • Lunches on the road.

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 regarding our Tuscany Bike Tours?

See our FAQs page for answers to common questions.

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Bike Hire & Gear

Full Carbon Road Bikes

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


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.


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.

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 and peasant traditions or ‘cucina povera’. 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.



The ride routes took us through iconic Tuscan landscapes, towns and villages, and when you thought the scenery cold not get better, around the next corner it did. The free-flowing, sweeping descents were an exhilarating reward for the climbing beforehand.

Michael F


We would sincerely like to thank you both for an inspiring, amazing, enlightening and wonderful trip around beautiful Tuscany. We were so impressed with the diversity and attention to detail you achieved in putting this together for us. Every moment was special. Every moment was exciting and rewarding.

Teresa & Peter S


Thank you so much for the amazing tour of Tuscany. The countryside lived up to its reputation as seen in countless books and movies. The experience you gave us was superb. The accommodation, the riding, the food, wine, spa, tours and the company were first class. We will have happy memories for years to come.

Pat & Paul B


My Tuscany cycling tour in September 2018 with Damian and Nancy exceeded all expectations, a wonderful combination of scenery and gourmet delights along with wonderful accommodation in Tuscan villas.  This tour was the most rewarding active holiday experience and I recommend A’qto Cycling Italian cycling tours without hesitation.

Peter Mile
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