Cycling Holiday Tuscany
Discover the Ultimate Tuscany Cycling Holiday
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.
Premium Tuscany cycling holidays
Tuscany, a land of beauty, elegance, and dreams. Where the colours of the landscape, the great scenery of the Tuscan hills, and the flavours of 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 holidays surrounded by incredible panoramic views of rolling hills, olive groves, cypress trees, vineyards, and medieval hilltop towns, all while embracing the winding quiet roads, challenging climbs, and exhilarating descents on two wheels.
Rediscover your taste for adventure on our Tuscany cycling holiday as you pedal along quiet 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 favorite 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 Cycling Tour
Immerse yourself in the Tuscan landscape with daily cycling tours across 7 consecutive days through the Chianti hills, the undulating hills of Val d’Orcia, and the idyllic San Gimignano (a UNESCO World Heritage site) area. Our carefully selected accommodations offer ample free time to relax and savor the beauty of your surroundings post ride. Our tours also have meals included and an active program for non-riding partners.
Welcome to ChiantiFollowing 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: 35.9km
Elevation: 719m
To Siena & BeyondIt’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: 89.6km
Elevation: 1601m
Climbers ParadiseToday you explore the beauty and challenge of the Chianti hills, with the ride including more sustained climbing with 5 distinct climbs as we traverse through some of the most iconic vlilages between Siena and Florence.
Highlight: The free flowing descents that follow the 5 climbs.
Distance: 75km
Elevation: 1733m
South of SienaToday’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: 82.6km
Elevation: 1662m
A Renaissance adventureToday you set off in the direction of Umbria, in true L’Eroica style you take to the ancient Roman roads (affectionately
known as the Strade Bianche) as you traverse through this postcard perfect landscape and pretty villages, before reaching one of Tuscany’s prettiest towns, Montelpuciano.
Highlight: The open rolling hills of the Val d’Orcia
Distance: 67.2km
Elevation: 1354m
Into Brunello CountryYour 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: 68.1km
Elevation: 1286m
Our Tuscany bike tour takes you to the town of 14 towersThis 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: 105.3km
Elevation: 1631m
Pricing & Dates
Join Us for an Unforgettable Cycling Adventure
Ready to explore the spectacular landscapes of Tuscany, Italy? Book your cycling tour with us today and experience the perfect blend of challenging riding, adventure, reward and cultural immersion. Discover why Tuscany is one of the world’s most sought-after cycling destinations.
7595
per person twin share / Maximum 14 guests
Show Price As
2025
2026
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
Everything you need for a perfect cycling holiday.
Accommodation & Meals
- We offer 7 nights' accommodation with private bathroom
- Twin-share rooms, with single occupancy options available (please enquire at booking)
- Daily breakfast
- Lunch while cycling
- A Tuscan dinner each evening at a selection of our favourite local restaurants and osterias, accompanied by local wines*
- *Please note: Wine provided at dinner complements your meal. Additional beverages ordered by guests will incur extra charges.
Ride Support
- Our professional bilingual ride guides bring extensive cycling expertise, local knowledge, and first aid skills to ensure your rides are authentically local, exploring hidden back roads and the rolling hills of this stunning and diverse region.
- On tour, we provide unique GPS routes as part of our Tuscany bike tours.
- We have a support van that accompanies daily rides, offering mechanical assistance and prioritising your safety. Nutritious snacks and water are also provided throughout your rides each day.
Transfers & Activities
- All ground transportation from your pick-up location to your drop-off point is included. This covers both you and your luggage, as well as bike transport if applicable.
- For non-riding companions, entrance fees to all included sites and tours are covered.
Ride Kit
- Experience the ultimate cycling comfort with our 2-piece Italian-made A'QTO Cycling Kit, featuring a high-performance jersey and bib shorts.
- Convenient laundry service for your cycling gear is also provided.
Not Included
- Bike hire
- Airfare
- Travel and international medical insurance
- Guide gratuities
- Certain energy bars and gels
Bike Hire & Gear
Wilier Cento10 SL Carbon Road Bike with Electronic Shifting
You can choose to hire a Wilier Cento10 SL carbon road bike with Sram Rival Etap, a compact crankset, with a 32 rear cassette & disc brakes.
Carbon Road Bike with Mechanical Shifting
You can choose to hire a Bianchi Sprint with mechanical Shimano Ultegra groupset, a compact crankset, with a 32 rear cassette & disc brakes.
Non-Riding Partners
As part of our cycling holiday in 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 it’s guided walks in the hills of Chianti and the Val d’Orcia, visits to beautiful castles and hilltop towns, including Siena’s iconic Piazza del Campo or medieval villages like San Quirico d’Orcia, meet-the-producer experiences, or cooking classes and visits to local artisans, non-riding partners experience the beauty and uniqueness of each area we visit. Each itinerary is closely curated by Nancy and delivered together with a range of partners and guides she personally selects, so 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.
Accommodation
Enjoy our hand-picked selection of boutique hotels and family-run villas across Tuscany that reflect the true character of the region and its beautiful, warm, and open people with whom we’ll share our experience. We ensure each accommodation we partner with is secure, comfortable and clean, and has the right ambience for an authentic cycling holiday in Tuscany.
Our accommodations are situated in stunning locations, with some offering panoramic views of the Tuscan countryside and some located within the vibrant atmosphere of an old town, providing easy access to local shops, restaurants and cultural attractions.
Food & Wine
Together, we’ll enjoy culinary delights and wines from the different areas of Tuscany.
The lure of the Tuscan table is immense — characterised by its close association with the land, Tuscan cuisine is earthy, simple, and reflective of the region’s changing seasons. We will take you on a culinary journey of Tuscany that takes in all the very best it has to offer, from simple organic produce grown on our hosts’ properties to exquisite gastronomic delights such as Pecorino cheese, truffle and freshly pressed olive oil at selected family-run osterias and restaurants, located in small villages and in the tiny backstreets of hilltop towns.
Our culinary journey will see you taste delicious food from diverse regions of Tuscany and include the option to indulge in a truly authentic wine tasting. Every meal is an opportunity to connect with the heart of Tuscany as you enjoy delicious cuisine and the warmth of our hosts which will surely leave an indelible impression on you as you enjoy the rewards of your cycling holiday in Tuscany.
Testimonials
THOUGHTFULLY PLANNED & SEAMLESSLY EXECUTED
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. The atmosphere throughout the tour was warm, friendly and inclusive and there was a good balance between riding/activities and free time. The accommodation was exceptional, with locations appropriately chosen to make the most of the beautiful Tuscan landscapes and the hosts were warm and friendly, making you feel as though you were part of their family.
Frequently Asked Questions
To prepare for a cycling tour, it’s recommended to engage in consistent training for about 8 to 12 weeks prior to the tour. Aim for 3 to 5 rides per week, gradually increasing your distance and intensity. Focus on building endurance with longer weekend rides and incorporate hill training if the tour includes mountainous terrain. Additionally, strength training and core exercises can help improve your overall cycling performance and stamina. Adjust your training based on your current fitness level and the difficulty of the tour.
We can offer e-road bikes for experienced riders on our cycling tours in Italy. While nearly all riders on our cycling tours use traditional road bikes, there are circumstances where we accommodate e-road bikes.
Want to learn more about our Tuscany cycling tour?
- Check out our FAQ section.
