Luxury Tuscany & Vineyards
The very best of Tuscany can be discovered when going beyond the guidebook.
A Luxury Ride Through Tuscany’s Gems and Chianti Vineyards
Join us on an unforgettable bike tour through the heart of Tuscany, where every pedal stroke leads you to sun-kissed, ancient towns like Florence, Siena, Pisa, Pienza, San Gimignano, and Montecatini Terme - all proud UNESCO World Heritage Sites.
Cycle through breathtaking landscapes that seem straight out of a storybook, with routes thoughtfully designed for riders of all levels. Along the way, savor authentic Chianti wines as you relax in charming, family-run vineyards and truly discover what Chianti wine tastes like.
Throughout the tour, we’ll share insider tips on how to experience the iconic Strade Bianche - whether watching the race or riding its legendary routes yourself. New to cycling in Tuscany or a seasoned rider, you’ll find a journey that seamlessly combines culture, adventure, and the vibrant tastes of this remarkable region for an unforgettable experience.
Guided Rides
Non-Rider Welcomed
Wine Tasting
Transfers
Walking Tour of Siena
Truffle Hunting
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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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
- Ride through Chianti vineyards to charming Greve
- Climb to Castellina and its hilltop history
- Conquer the legendary Strade Bianche
- Discover towers of San Gimignano and Monteriggioni
- Cross the lunar hills of the Crete Senesi
- End with a scenic spin to Montepulciano
Itinerary
32 km | 570 m
Your Tuscan adventure begins! Upon arrival, you'll meet your friendly guide and head straight to your hotel where, once settled, we'll ensure you're perfectly set up with a professional bike fit.
With your bike ready, we ignite your imagination with a captivating welcome ride toward Greve in Chianti. This quintessential town hosts the Chianti Classico wine festival and sits near the magnificent Villa Vignamaggio, a historic villa belonged to the family of Mona Lisa Gherardini, immortalized by famous painter the Leonardo Da Vinci.
This first spin isn't just about "getting from A to B"; it's your first deep breath of the region - an immersion into the history, beauty, and Chianti wine culture that makes Tuscany unforgettable.
Hotel Villa Le Barone | Panzano in Chianti
54 km | 870 m
Prepare to climb deep into the heart of the Chianti Classico region. Our route takes on the area's iconic, rolling Chianti Hills, which are crowned with majestic medieval towns, still enclosed by their original seven-century-old stone walls.
Our destination and well-earned reward is the stunning hilltop fortress of Castellina in Chianti. Take a moment here to soak in the serene beauty, a peaceful contrast to the historic conflicts between Siena and Florence that defined this land.
But the real highlight awaits: a perfect, well-deserved Italian gelato to celebrate the climb before we return to the hotel!
Hotel Villa Le Barone | Panzano in Chianti
62 km | 1050 m
Our journey continues as we descend from the fortified hilltop village of Radda in Chianti toward the picturesque town of Gaiole in Chianti.
Gaiole is the gateway to some of Tuscany’s most legendary cycling. It is the birthplace of the famous Strade Bianche race, which follows the rustic, white gravel farm routes that dramatically crisscross the Tuscan panorama. Near here also stands the stunning Brolio Castle, a symbol of the region’s enduring history.
As the spires of Siena come into view, prepare to be completely overwhelmed by its medieval sublime. The grand finale of this leg is one of Italy's most beautiful, historic cities.
Hotel Belvedere di San Leonino | Castellina in Chianti
47 km | 680 m
Prepare for an astonishing and unforgettable day of cycling through history, castles, and medieval skyscrapers!
After a good breakfast, today's ride first brings us to the storybook castle of Monteriggioni. This entire fortified town, famously featured in the movie Gladiator, is completely encircled by a crown of imposing walls - a breathtaking sight that truly transports you back in time.
Next, we head to San Gimignano, a magnificent UNESCO World Heritage Site. Known as the "Medieval Manhattan," San Gimignano's noble families once competed to build the tallest towers, with 72 rising above the town in the 13th century. Today, fourteen of these magnificent towers still dominate the sky.
Hotel Belvedere di San Leonino | Castellina in Chianti
55 km | 970 m
Prepare for a truly unique cycling experience across the Crete Senesi, the "clays of Siena." You will ride over what was, for two million years, an ancient ocean seabed. Today, this land of grey-blue clay, chalk, and rock salt creates an otherworldly landscape, often compared to the surface of the moon.
Our cultural ride visits historic villages: Asciano, a 13th-century Sienese stronghold, and Buonconvento, showcasing Sienese landscape painters.
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, Brunello di Montalcino.
Hotel Relais il Chiostro di Pienza | Val d'Orcia
30 km | 540 m
We start the morning early, setting off toward Montepulciano, one of Tuscany’s most famous and charming hilltop towns. Enjoy a leisurely ride through rolling landscapes, culminating in a stop for a well-deserved coffee in the heart of this iconic village.
After soaking in the sweeping views and unforgettable atmosphere, we return to the hotel for check-out. It’s time to say arrivederci to Tuscany after an truly unforgettable cycling experience.
Dates & Prices
| Dates | Price | Availability | ||
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| Sun 12 Apr - Fri 17 Apr | From €3399 |
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| Sun 26 Apr - Fri 01 May | From €3699 |
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| Sun 10 May - Fri 15 May | From €3799 |
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| Sun 24 May - Fri 29 May | From €4099 |
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| Sun 07 Jun - Fri 12 Jun | From €4099 |
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| Sun 21 Jun - Fri 26 Jun | From €4099 |
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| Sun 30 Aug - Fri 04 Sep | From €4099 |
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| Sun 13 Sep - Fri 18 Sep | From €4099 |
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| Sun 27 Sep - Fri 02 Oct | From €3799 |
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| Sun 11 Oct - Fri 16 Oct | From €3699 |
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| Sun 25 Oct - Fri 30 Oct | From €3499 |
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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?
- 5 nights' in a 4* accommodation
- Transfers (from specified airport/train location)
- All breakfasts
- 3 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
- Truffle hunting
- 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 looking to enjoy a leisurely ride while savoring the "bella vita".
- Total Kilometres: Approx. 250 km (155 miles) of scenic, moderate rides through Chianti vineyards, medieval hill towns, and UNESCO landscapes.
- When: April to October offers ideal temperatures for cycling and savoring Tuscany
- Start: Florence Train Station - easily accessible from major European hubs.
- Finish:Val d’Orcia (Pienza) - transfer back to Florence Train Station included.
- 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 Florence Train Station (Santa Maria Novella) at 2pm. 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 alternative 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 the first hotel is approximately 1 hour. Transfer back to Florence train station on the last day takes around 2 hours. |
| Riding in Tuscany | The general road conditions in Tuscany are good, and most roads are quiet with light traffic. The majority of the roads are tarmac, but we will also be riding on some gravel roads - these are well maintained and enjoyable whether you’re on a road, gravel, or E-bike. |
| Cuisine | The food in Tuscany is exceptional, with a variety of local specialties to enjoy. Restaurants now cater for both vegan and vegetarian diets. Homemade local red wines like Brunello and Chianti are a must-try! |
| Hotel Facilities | The hotels on this tour have pools, so we recommend bringing swimming costumes. Hotels also provide good Wi-Fi, bar service, and air conditioning. Some facilities may incur an extra charge. |
| Private Tours & Groups | We welcome the opportunity to discuss a private tour with you if you are in a group of six or more. A private tour allows you to choose dates and personalize the itinerary according to your preferences. |
| Weather | The weather in Tuscany is excellent during the spring and autumn months. It can be hot in July and August, so those who prefer cooler riding conditions should consider joining us in April, May, September, or October. Ride times may be adjusted to account for 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 do not receive a response. You can also find a contact form at the bottom of this page. If you’d like help arranging any hotels or activities before or after your tour, please contact lynn@italybiketours.com. |
Hotels
HOTEL VILLA LE BARONE ★★★★
HOTEL BELVEDERE SAN LEONINO ★★★★
RELAIS IL CHIOSTRO DI PIENZA ★★★★
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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
