Tuscany Cycling Tour

Discover the Chianti, Val d’Orcia & San Gimignano

Have you been dreaming of cycling through Tuscany? Picture this, riding along rolling ridgelines of green hills, past endless rows of vineyards & olive groves & brushing past fields of wild red poppies. On this Tuscany Cycling Tour you’ll climb to medieval walled cities where you’ll feast on fresh pasta with rich sauces.

There really is only one Tuscany, and Lifecycles Travel has combined the best cycling routes with the most authentic dining experiences. This carefully crafted bespoke itinerary brings you to the absolute best of Toscana. Join us for 9 days in Tuscany & have the ride of your life.


Take a closer look at more Tuscany Cycling Tour highlights, download the trip itinerary:

Chris Boogert Lifecycles Travel Guide

Varied rides

We pride ourselves on creating experiences that are ideal for everyone. Don't let the spectacular scenery fool you there are challenging routes, but it's your choice to take them. Multiple daily ride options cater for both avid and recreational cyclists. Whether you want to go hard or go easy on any day, we’ve got the rides, support and logistics to suit you.

Alice and Chris owners of Lifecycles Travel

Expert staff

Meet your guides Chris and Alice!
They'll take you to sought after cycling destinations without making you feel like a tourist. Every ride, town, hotel and restaurant has been carefully researched and selected by these two. They are fun, energetic & are ready to show you a great time. "We absolutely love and believe in what we do, and can’t wait to share with you the ride of your life".

Kerrie and Pamila enjoy Lifecycles Travel

Bike Rental

Road and E-bike rental is available on this trip. Bikes can be damaged in transit. That's why we suggest renting a bike. Take the hassle out of your travel and arrive in Italy ready to ride. Choose from a selection of premium Willier models to suit your taste and ability. Request bike rental in your booking and we will request more specifics and pair you with your ideal bike.


  • Tuscany Cycling Tour 2020 $5999pp, twin share

    Standard price.

  • Single Supplement $1200 additional

    For solo travellers who desire a private room at each hotel.

Got any questions?


Thursday 14th May – Trip commences at Florence Airport
Enjoy a private airport transfer to San Gimignano, one of the most iconic and recognisable destinations in Tuscany, to start the trip. You’ll be set up on your bike for the tour while enjoying panoramic views of the countryside, leaving time in the afternoon for a short spin up to the medieval city to warm-up your legs and experience this UNESCO world heritage listed destination. A special welcome dinner tonight sampling typical Tuscan dishes including duck ragout and tiramisu washed down with local Vernaccia di San Gimignano wine.

Today the real cycling begins with a magnificent loop along the valleys of Cecina and Dell’Era, before climbing up to the Etruscan town of Volterra where you can witness one of the finest and most well preserved Roman theatres in Italy before taking a coffee overlooking the wonderful Palazzo dei Priori in the town centre. Enjoy an afternoon by the pool or on the hotel terrace before we regroup tonight for a gourmet Italian cooking class, where we’ll learn how to make local pastas and desserts from an experienced Italian chef. 

    • Ride details: 80km, 1300m climbing
    • Shorter option: 50km, 800m climbing
    • Longer option: 90km, 1500m climbing

This morning we’ll enjoy a unforgetable ride in the envious oasis of the Val d’Elsa, absorbing the beauty of this postcard landscape as we navigate our way to the walled city of Certaldo, which unlike other villages dating to the middle ages, is recognisable for having no main piazza from where religious or other commercial powers would have once made their mark. Returning back to San Gimignano on scenic roads, we’ll shower and change before visiting a local winery this afternoon for a tasting and picturesque 4 course lunch in the vineyards

    • Ride details: 72km, 1150m climbing
    • Shorter option: 50km, 650m climbing
    • Longer option: 80km, 1300m climbing*

Today we swap one postcard Tuscan landscape for another as we say goodbye to San Gimignano and ride south to the iconic Val d’Orcia. Along the way, we’ll tackle the infamous ‘white roads’ around Siena and get a taste of what the pros experience in the famous Strade Bianche pro-tour race. Arriving in San Quirico, you’ll be met with inviting paved streets and past beautiful stone fountains. This evening, enjoy an aperitif Spritz while watching the sun set over the valley before dinner at a local restaurant in the ancient walled city

    • Ride details: 80km, 1000m climbing
    • Shorter option: 45km, 500m climbing
    • Longer option: 100km, 1700m climbing

Journey deep into the heart of the Val d’Orcia today as we ride south to Radicofani to witness one of the most spectacular fortresses in Tuscany. The rolling hills lined with poppy fields and Cypress trees that fill this unmistakable region to the south of Siena have been immortalized through millions of photographs, as well as films such as Gladiator and The English Patient. No doubt you will enjoy a few photo ops along the way yourself before we eventually arrive back in San Quirico in time for an afternoon visit to Bagno Vignoni for a dip in the natural hot springs here first discovered by the Etruscans

    • Ride details: 65km, 900m climbing
    • Shorter option: 35km, 500m climbing
    • Longer option: 80km, 1500m climbing

It’s time for us to depart the Val d’Orcia this morning as we continue onto our final destination of this tour, the world famous Chianti region. Riding out of San Quirico, we’ll soon pass through the Crete Senesi and witness the lunar appearance of the landscape in this region caused by the distinctive grey colouration of the clay earth. Further north in Gaiole, a visit to the birthplace of the Chianti Classico DOCG awaits at Italy’s oldest winery Castello di Brolio, before we continue to our finish in Radda in Chianti, a typical Tuscan town dotted with a sea of vineyards.

    • Ride details: 70km, 1100m climbing
    • Shorter option: 50km, 700m climbing
    • Longer option: 86km, 1400m climbing

Watch the morning fog lift out of the valley while enjoying coffee and croissants before we dive into the luscious, rolling chain of Chianti hills on our ride to Monteriggioni. This tiny medieval city, perched idyllically on a hill-top and perfectly wrapped inside a 570m perimeter wall with 14 towers, is arguably one of the most beautiful towns in all of Italy and our destination for coffee on today’s ride. This afternoon, we’ll visit one of Castellina’s best wineries Poggio Amorelli, owned and operated by the Mazerrini family, who will guide us through a tasting of their homegrown Sangiovese, Super Tuscan and other notable blends, matched with typical Tuscan flavours from the kitchen.

    • Ride details: 62km, 1100m climbing
    • Shorter option: 36km, 600m climbing
    • Longer option: 93km, 1650m climbing

No trip to Tuscany would be complete without navigating the iconic ‘Chiantigiana’. This scenic tourist route, linking Florence and Siena, takes in Chianti’s best destinations Greve, Panzano and Castellina, whilst offering endless views of hills, vineyards, olive groves, villages and castles. This afternoon, you’re free to wander the tiny streets of Radda before we regroup for a farewell dinner at Bar Ucci in nearby Volpaia, where owner Paola will explain the history of this cattle-shed turned wine bar over a selection of hearty local dishes. 

    • Ride details: 67km, 1200m
    • Shorter option: 50km, 950m
    • Longer option: 90km, 1550m climbing

Friday 22nd May – Trip concludes at Florence Airport
Tuscany Cycling Tour! It’s always sad to say goodbye, but like all good things the trip must come to an end. Following breakfast at the hotel, we will arrange private transfers to Florence Airport & Train Station, where the trip will conclude. Enjoy the rest of your travels and we look forward to seeing you on a Lifecycles Travel trip again soon.

Some of the Hotels & Restaurants You'll experience on tour

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Take a look!

Find out where we’ll be staying, see the ride maps and the day by day details of this amazing holiday…