Unexpected Tuscany
A Seven-Day Tuscany Cycling Adventure Through Vineyards, Medieval Villages, and Scenic White Roads
Experience the Beauty, Flavors, and Spirit of Tuscany
Experience the joy of Italy’s best cycling on a seven-day journey through Tuscany’s rolling hills, charming villages, and breathtaking landscapes. From Lucca to Radicofani, follow the historic Via Francigena, an ancient unpaved path that winds through medieval towns alive with art, history, and local culture.
Each day brings a new adventure, with your essentials safely in the support van while you ride scenic dirt roads and peaceful paths, including stretches that echo the legendary Strade Bianche, letting you feel the thrill of Italy’s most iconic cycling routes. Awaken your senses with every pedal stroke - Chianti wine tasting, local delicacies, and the rich flavors of Tuscany await at every stop.
Set off on a cycling adventure through Italy that will inspire you, delight your senses, and leave you with unforgettable memories.
Historic Siena
Non-Rider Welcomed
Wine Tasting
Transfers
Guided Rides
Sunrise Ride
Guest Reviews
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!
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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!!
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I had an unforgettable experience with Italy Bike Tours team - Unexpected Tuscany on a multi-day cycling tour through some of the most beautiful towns in the region: San Miniato, San Gimignano, Siena, Montalcino, and Montepulciano. Each ride was about 50 - 60 km, taking us through stunning Tuscan landscapes filled with vineyards, rolling hills, and quiet countryside roads.This wasn’t just a tour; it was a deeply memorable way to experience the heart of Tuscany. Beautiful routes, great company, delicious food and wine, and top-notch guidance. Highly recommended!
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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.
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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
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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.
Read moreIn the Saddle
WHAT TO LOOK FORWARD to on-bike
- Explore Lucca’s historic city streets and walls
- Pedal the rolling hills of Val d’Elsa
- Enter Siena triumphantly at Piazza del Campo
- Ride scenic dirt roads lined with cypress trees
- Enjoy sweeping views of the Val d’Orcia
- Discover the otherworldly Crete Senesi landscapes
beyond the ride
What to look forward to off-bike
- Stroll charming streets, historic churches, and picturesque squares
- Savor the best gelato in San Gimignano
- Explore Siena
- Visit quaint villages like Buonconvento and San Giovanni d’Asso
- Taste Tuscany’s finest wines
- Sip the best cappuccino at cozy local cafés
Itinerary
49 km | 300 m
Your Tuscan adventure begins! One of our friendly guides will meet you at Firenze Train Station to begin your cycling adventure. 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 breathtaking scenery. We’ll start with a beautiful cycle along the ancient walls of Lucca, a city brimming with charm and history.
The day concludes in San Miniato, where rolling hills and warm hospitality create the perfect end to an unforgettable first day on the road.
San Miniato | Tuscany
52 km | 810 m
A truly splendid route awaits today. Shortly after leaving San Miniato, the path unfolds along the rolling ridges of the Val d’Elsa, enchanting every rider with its extraordinary beauty.
The arrival in San Gimignano is nothing short of magical - emerging from a quiet country road, the medieval towers rise before you in all their timeless charm. Take time to wander through the cobbled streets and soak in the village’s unique atmosphere.
Tonight, you’ll stay in a beautiful country farmhouse overlooking the golden hills of San Gimignano, the perfect setting to relax and reflect on the day’s ride.
San Gimignano | Tuscany
62 km | 820 m
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 winds through gentle ups and downs, linking ancient hamlets where time seems to stand still.
The arrival in Siena feels truly triumphant - we walk the final stretch to Piazza del Campo, savoring every moment of this unforgettable conquest. Tonight’s stay is in a charming farmhouse just outside Siena, surrounded by the peace of the Tuscan countryside.
Siena | Tuscany
51 km | 690 m
The landscape changes once more as we enter the Crete Senesi, the “clays of Siena,” often compared to the surface of the moon. Gentle valleys, white gravel roads, and elegant rows of cypress trees create a landscape of pure beauty.
We are now in the very heart of Tuscany. Tonight, we’ll stay in a beautifully restored granary in the medieval village of Serre di Rapolano, surrounded by timeless charm.
Rapolano | Tuscany
59 km | 990 m
Between the striking Crete Senesi and the breathtaking Val d’Orcia, San Giovanni d’Asso marks the halfway point to Montalcino - once a medieval stronghold and now the home of two world-famous wines, Brunello and Rosso di Montalcino
Along the way, the route passes through Buonconvento, a charming walled village dating back to 1383. Its name, from the Latin Bonus Conventus meaning “happy, lucky place,” makes it the perfect stop to rest and enjoy some delicious local food.
The day concludes in Montalcino with a planned dinner where you will enjoy traditional Tuscan dishes paired with the region’s iconic, world-renowned wine.
Montalcino | Tuscany
53 km | 910 m
The time has come to immerse yourself in the breathtaking landscapes of the Val d’Orcia, where San Quirico and Pienza take center stage. The beautiful hilltop town of San Quirico d’Orcia dates back to ancient times and even appears in the Liber Linteus Zagrabiensis (300 BC), the oldest known book in Western Europe.
As you approach the UNESCO World Heritage Site of Pienza, you’ll understand why it’s often described as the embodiment of perfect beauty.
The day ends in Montepulciano, world-famous for its fine wines, where we’ll enjoy a well-deserved evening at an organic winery.
Montepulciano | Tuscany
40 km | 890 m
The final stage of our journey is full of unforgettable sights. Monticchiello, a charming medieval village, welcomes us amidst the rolling hills of the Sienese countryside.
Following the historic Via Francigena, the route ascends the hills of the Val d’Orcia, culminating in the last climb to Radicofani, where spectacular panoramas mark the grand finale of this incredible cycling adventure.
From here, we’ll return to Florence by private transfer.
Dates & Prices
| Dates | Price | Availability | ||
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| Sun 05 Apr - Sat 11 Apr | From €2999 |
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| Sun 19 Apr - Sat 25 Apr | From €3499 |
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| Sun 10 May - Sat 16 May | From €3499 |
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| Sun 31 May - Sat 06 Jun | From €3699 |
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| Sun 14 Jun - Sat 20 Jun | From €3699 |
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| Sun 28 Jun - Sat 04 Jul | From €3699 |
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| Sun 30 Aug - Sat 05 Sep | From €3699 |
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| Sun 13 Sep - Sat 19 Sep | From €3699 |
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| Sun 27 Sep - Sat 03 Oct | From €3499 |
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| Sun 18 Oct - Sat 24 Oct | From €2999 |
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Ridley Bikes & Gear
Ridley ASTR GRX600 – Explore epic landscapes! Lightweight, responsive, and adventure-ready. Perfect for gravel, touring, and thrill seekers.
Ridley Kalazy – Cruise in comfort with flat handlebars, smooth ride, and stylish design. Ideal for relaxed, scenic holiday cycling.
Ridley Urbx Mixte E-Bike – Glide through your holiday with ease; upright comfort, smooth handling, and stylish design making every ride relaxing, scenic, and unforgettable.
COLNAGO V3
COMPONENTS:
- Shimano 105 12 Speed Di2 Drivetrain (50/34 Chainset and 11-34 Cassette)
- Fulcrum Racing 600 Wheelset
- Pirelli P7 Sport 28mm Tyres
- Shimano 105 Hydraulic Disc Brakes (160mm rotors)
- Selle Italia Novus Boost Evo Flow saddle
- (Sizes: XXS(42S), XS(45S), S(48S), M(50S), L(52S), XL(54S), XXL(56S), XXXL(58S))
3T ULTRA
COMPONENTS:
- Shimano GRX 822 1x - 40T 1x Chainset, 12 Speed 10-51T Cassette
- Fulcrum Rapid Red 900 Wheelset
- Shimano GRX Hydraulic Disc Brakes (160mm rotors)
- Selle Italia Model X Superflow
- Sizes: 48 - 61
The nuts and Bolts
What's Included?
- 6 nights' 3* or 4* accommodation
- Transfers (from specified airport/train location)
- All breakfasts
- 4 dinners
- Bike hire & helmet
- Water and coffee are complimentary during meals that are included in the package
- Beautifully planned rides
- Experienced team of local professionals
- GPX Routes
- Van and mechanical support with snacks and water
- Wine tour & tasting
- Bike cleaning service
- IBT cycling jersey
- IBT water bottle
- City taxes
What's Not Included?
- Travel insurance (must be purchased before the tour)
- Flights
- Beverages
- Lunches
- Nutrition
- Tips and gratuities
At a Glance
- Level: Perfect for casual cyclists and e-bike enthusiasts who want to enjoy relaxed rides while soaking up the Tuscan lifestyle.
- Total Kilometres: Around 366 km (227 miles) of scenic rides through Chianti vineyards, medieval towns, and the UNESCO-listed Val d’Orcia.
- When: April to October – ideal for mild weather and beautiful Tuscan landscapes.
- Start: Panzano in Chianti.
- Finish: Pienza, in the beautiful Val d'Orcia.
- Nearest Airport: We recommend looking into flights in Florence or Bologna.
- Top Tip: Italians... dine late! Refuel with a gelato mid-ride and enjoy dinner after sunset like a local.
- Average Age of Guest:Average age around 55, with a welcoming mix of couples, solo travelers, and women’s friend groups.
- Male vs Female %: Approximately 60% female participation, though perfect for mixed or small private groups.
| Where to Meet | Please plan to meet us at Lucca Train Station (Santa Maria Novella) at 12pm. Your guides will contact you via WhatsApp 24 hours in advance to confirm the name of the staff member meeting you. |
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| Drop off Location | Following the conclusion of the tour we will assist you with planning and booking of 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 us at alberto@italybiketours.com |
| Transfer Time | Please consider eating lunch before we collect you from Florence. The transfer time from Florence to Panzano in Chianti on Day 1 is approximately 1 hour. Transfer back to Florence train station on the last day is around 1h45. |
| Riding in Tuscany | The general road conditions in Tuscany are good, and most routes are quiet with light traffic. The majority of roads are tarmac, but we will also be riding on some gravel roads — they are in good condition and suitable for road, gravel, or E-bikes. |
| Cuisine | The food in Tuscany is excellent, with many local specialties to look forward to. Restaurants cater for both vegan and vegetarian diets. Homemade local wines and beers are a must-try. |
| Hotel Facilities | The hotels on this tour have pools, so we recommend bringing swimming costumes. Hotels also have good Wi-Fi and bar service, and all have air conditioning. Some facilities may incur an additional charge. |
| Private Tours & Groups | We welcome the opportunity to discuss a private tour with you should you be in a group of six or more. A private tour allows you to choose dates and personalize the itinerary according to your requirements. |
| Weather | The weather in Tuscany is excellent for most of the year. It can be hot in July and August, so those who prefer cooler conditions should consider joining us in April, May, September, or October. Ride times may be adjusted to take into account extreme weather events. |
| What Happens Next? | Are you thinking about joining us? You probably have some questions! The best way to contact us is by email — we will reply within 24 hours. Please check your SPAM/JUNK folder if you have not received a response. You can also find a contact form at the bottom of this page! |
Hotels
HOTEL MIRAVALLE ★★★★
IL CASTAGNOLO COUNTRY B&B ★★★★
CHIOSTRO DEL CARMINE ★★★★
ANTICO GRANAIONE B&B ★★★★
HOTEL VECCHIA OLIVIERA ★★★★
SALCHETO ORGANIC WINERY ★★★★
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Get In Touch
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!
ITA: +39 320 638 4713
Or you can chat to us online by clicking the button at bottom right of page.
Drop us a direct email to: info@italybiketours.com
