Tuscany Cycling Tour
A land of elegance, beauty and dreams
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 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
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
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.
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
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
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
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
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.
Pricing & Dates
per person twin share / Maximum 14 guests
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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
Transfers & Activities
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?
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.
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
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.