Experience the Beauty, Flavors, and Spirit of Tuscany
Experience one of Italy’s most rewarding family-friendly cycling adventures on a seven-day journey through Tuscany’s rolling hills, charming villages and spectacular countryside.
From Lucca to Radicofani, follow sections of the historic Via Francigena, an ancient route winding through medieval towns rich in art, history and local culture.
Each day brings a new adventure, while your luggage and essentials travel safely in the support van, leaving you free to simply enjoy the ride.
Ride scenic dirt roads and peaceful country lanes, including sections inspired by the legendary Strade Bianche, and experience some of Tuscany’s most distinctive cycling terrain.
Away from the bike, discover the flavours of the region with Chianti wine tasting, traditional dishes and authentic local experiences along the way.
Unexpected Tuscany combines cycling, culture and food in a journey designed to be shared — an active, relaxed way to experience one of Italy’s most beautiful regions.
Thanks to Italy bike Tours! It was not just a cycling tour — but we created timeless memories with them, friendships and quite moments through out our tour which we’ll cherish for a lifetime.
An epic, and for me super challenging week cycling non elec bikes over the rolling Tuscan hills! Matteo is an excellent and patient guide aided by Andrea on water van duty. Great company, super food and left feeling super satisfied on this our second tour. Looking forward to next year!
The guys are super pros, I felt really safe at all times during the trip. John and Ivan made us feel comfortable 100% of the time, always knew the way, alternative routes, where to take us and where to stop, how difficult it would be day by day, so it was amazing. They also let us pretty relaxed to take our time and enjoy the ride. I definitely want to come back!!
10 out of 10. There is nothing to fault. Great to eat local food and drink local wine, the accommodation was always good, the scenery was picture postcard beautiful and our guides, Fausto, Giovanni and Carlo were amazing. Always cheerful and nothing was too much trouble Thank you for a wonderful experience. I highly recommend this tour.
I successfully completed this IBT tour, which more than exceeded its name. I loved it! I was very apprehensive on my first day, but hey!, it turned out I was a natural. The route was amazing, the scenery dreamlike, the organization seamless. But the biggest accolade goes to Fausto, Giovanni, and Carlo - the BEST guides ever! Ciao Marianne
This e-bike tour was an adventure of a lifetime. Our tour director and all our hosts and guides were wonderful and well organized. Almost 400km of Tuscan hills that were challenging at times, but every stop and town were wonderful to visit. We would not have seen Italy in the same way, if it weren’t for the bikes. What a fun group to travel with! I’ll cherish these memories for a long time.
Discover Tuscany from two perspectives — memorable riding through its hills and white roads, alongside the food, villages and culture that make this region so distinctive.
Explore Lucca’s historic streets and ride along the city’s remarkable Renaissance walls.
Pedal through rolling Tuscan hills, vineyards and peaceful countryside.
Ride into Siena and finish in the heart of the city at Piazza del Campo.
Ride scenic dirt roads lined with cypress trees and classic Tuscan landscapes.
Enjoy sweeping views across one of Tuscany’s most recognisable landscapes.
Discover the distinctive rolling clay hills and dramatic scenery of the Crete Senesi.
Stroll through historic streets, churches and picturesque town squares.
Stop in San Gimignano and enjoy one of Tuscany’s classic gelato breaks.
Discover Siena’s medieval centre, historic streets and Piazza del Campo.
Visit villages including Buonconvento and San Giovanni d’Asso.
Taste some of the region’s celebrated wines and discover local winemaking traditions.
Take time for a cappuccino in a traditional Tuscan café.
Follow the Via Francigena through the heart of Tuscany — from Lucca and San Gimignano to Siena, the Crete Senesi, Val d’Orcia and the final climb to Radicofani.
Your Tuscan adventure begins! One of our friendly guides will meet you at Lucca Train Station. After completing the bike setup and a short trip briefing, we set off on the first stage of the journey.
Today’s ride unfolds through the heart of Tuscany, combining gentle terrain with beautiful scenery. We begin with a ride along Lucca’s ancient city walls, surrounded by the history and character of this remarkable Tuscan city.
The day concludes in San Miniato, where rolling hills and warm hospitality provide the perfect end to our first day on the road.
San Miniato | Tuscany
A truly splendid route awaits today. Shortly after leaving San Miniato, the route follows the rolling ridges of the Val d’Elsa through classic Tuscan scenery.
The arrival in San Gimignano is unforgettable. Emerging from a quiet country road, its medieval towers rise ahead above the surrounding countryside.
Tonight, you’ll stay in a beautiful country farmhouse overlooking the golden hills of San Gimignano.
San Gimignano | Tuscany
As we leave San Gimignano, it’s impossible not to glance back for one last look at its iconic towers before they disappear behind the rolling hills.
Soon, Monteriggioni comes into view. The route towards the castle follows gentle climbs and descents, linking ancient hamlets and quiet country roads.
The arrival in Siena feels truly triumphant. We walk the final stretch to Piazza del Campo before heading to our farmhouse just outside the city.
Siena | Tuscany
The landscape changes once more as we enter the Crete Senesi, the distinctive clay hills south of Siena. Gentle valleys, white gravel roads and rows of cypress trees create one of Tuscany’s most recognisable landscapes.
We are now in the very heart of Tuscany. Tonight, we stay in a beautifully restored granary in the medieval village of Serre di Rapolano.
Rapolano | Tuscany
Between the Crete Senesi and the Val d’Orcia, San Giovanni d’Asso marks the halfway point towards Montalcino, home of the celebrated Brunello and Rosso di Montalcino wines.
Along the way, the route passes through Buonconvento, a charming walled village dating back to the fourteenth century and an ideal place to stop for some local food.
The day concludes in Montalcino with a planned dinner featuring traditional Tuscan dishes paired with the region’s famous wine.
Montalcino | Tuscany
Today we immerse ourselves in the landscapes of the Val d’Orcia, where San Quirico d’Orcia and Pienza take centre stage.
As you approach Pienza, the sweeping views across the valley reveal why this part of Tuscany is so widely celebrated.
The day ends in Montepulciano, famous for its wines, where we’ll enjoy a well-deserved evening at an organic winery.
Montepulciano | Tuscany
The final stage begins with Monticchiello, a charming medieval village surrounded by the rolling hills of southern Tuscany.
Following the historic Via Francigena, the route climbs through the Val d’Orcia, culminating in the final ascent to Radicofani, where spectacular views mark the end of our cycling journey.
From here, we’ll return to Florence by private transfer.
Breakfast, coffee and views across the hills.
Ride quiet gravel roads through classic Tuscany.
Explore hilltop towns and historic streets.
Gelato, espresso or a relaxed Tuscan lunch.
Local dishes paired with a glass of regional wine.
Choose your departure and experience Tuscany by bike — from Lucca and San Gimignano to Siena, Montalcino, Montepulciano and the spectacular landscapes of the Val d’Orcia.
Choose the bike that best suits your riding style. All three options are included for the full duration of your tour.
Explore epic landscapes! Lightweight, responsive, and adventure-ready. Perfect for gravel, touring, and thrill seekers.
Cruise in comfort with flat handlebars, smooth ride, and stylish design. Ideal for relaxed, scenic holiday cycling.
Glide through your holiday with ease; upright comfort, smooth handling, and stylish design making every ride relaxing, scenic, and unforgettable.
Looking for a different bike model? Contact us at alberto@italybiketours.com
Everything you need to know before joining Unexpected Tuscany — from what’s included and transfers to riding conditions, local food, hotels and practical tour information.
Please plan to meet us at Lucca Train Station at 12 pm. Your guides will contact you via WhatsApp 24 hours in advance to confirm the name of the staff member meeting you.
Following the conclusion of the tour, we can assist with planning and booking onward travel. We will run one transfer to Florence Train Station (Santa Maria Novella), leaving the hotel at 10.30 am.
For other destinations or departure times, please contact alberto@italybiketours.com .
Please consider eating lunch before we collect you. The transfer from Florence to Panzano in Chianti on Day 1 is approximately 1 hour.
The transfer back to Florence Train Station on the last day is approximately 1 hour 45 minutes.
Road conditions in Tuscany are generally good, and most routes are quiet with light traffic. Most roads are tarmac, but we also ride some gravel roads that are in good condition and suitable for road, gravel or e-bikes.
Roads are shared with other vehicles, so normal road awareness and safe riding practices are always important.
Tuscan cuisine is excellent, with plenty of local specialities to enjoy along the way.
Restaurants generally cater for vegetarian and vegan diets, while local wines and beers are well worth trying.
Please let us know when booking if you have any specific dietary requirements.
The hotels on this tour have pools, so we recommend bringing your swimming costume.
Hotels also have good Wi-Fi, bar service and air conditioning. Some facilities may incur an additional charge.
We welcome the opportunity to discuss a private tour for groups of six or more.
A private tour allows you to choose dates and personalise the itinerary according to your requirements.
Absolutely. Non-riding partners are always very welcome on our tours. We offer dedicated non-rider experiences, allowing them to enjoy the destination in their own way while you’re out on the bike. Get in touch with our team to discover the non-rider options available for your chosen tour.
Are you thinking about joining us? You probably have some questions. Email is the best way to contact us and we aim to reply within 24 hours.
You can also use the contact form at the bottom of this page.
If you’d like help arranging hotels or activities before or after your tour, please contact lynn@italybiketours.com .
A collection of carefully selected hotels, country houses and wineries along the Unexpected Tuscany route — from San Miniato to Montepulciano.
More unforgettable journeys through Northern Italy and Tuscany — from the serene Italian Lakes to the rolling hills of Chianti.
Discover more cycling experiences, destinations and ideas for your next Italian adventure in our latest brochure.
View Our 2026 & 2027 Brochure →If you would prefer to give us a call and talk cycling and Italy, please WhatsApp us on the number below and we will arrange a call back.
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