Luxury Palio di Siena
Immerse Yourself in the Authentic Palio di Siena Experience:
Exclusive Access, Luxury Accommodations, and the Timeless Magic of Tuscany’s Most Iconic Horse Race
A Journey Through Tradition and Beauty
Step into the heart of Tuscany on a truly exclusive cycling adventure, where history, culture, and authentic experiences come together in perfect harmony. Your journey begins in Siena, a city steeped in tradition, where you will witness the legendary Palio horse race in the iconic Piazza del Campo - a centuries-old celebration of community, passion, and skill.
Pedal through the rolling Chianti hills, where vineyards, olive groves, and picturesque villages like Radda and Castellina reveal the timeless beauty of the Tuscan countryside. Ride along the famous Strade Bianche white gravel roads, taking in sweeping vistas of medieval towns and sun-drenched landscapes that few get to see. Explore the medieval towers of San Gimignano, wander its charming streets, and immerse yourself in the region’s history. Delight in hands-on experiences such as truffle hunting with local experts, and savor authentic Tuscan cuisine and fine regional wines in intimate, welcoming settings. Each evening, relax in carefully selected hotels tucked into stunning landscapes, sharing stories and laughter with fellow cyclists and your dedicated IBT guides.
This is Tuscany like no other - immersive, authentic, and unforgettable, with every moment crafted to inspire and delight.
Guided Rides
Non-Rider Welcomed
Wine Tasting
Transfers
Superb Hotels
VIP Entry Palio di Siena
Truffle Hunting
In the Saddle
WHAT TO LOOK FORWARD to on-bike
- Experience the Strade Bianche, Tuscany’s famous white gravel roads.
- Pedal through San Gimignano’s historic climbs.
- Cycle through vineyards, olive groves, and charming villages.
- Enjoy gentle rides through the rolling Chianti hills.
- Challenge yourself across varied terrain, from smooth roads to rolling gravel paths.
beyond the ride
What to look forward to off-bike
- Witness the Palio, one of the most thrilling and historic horse races in the world.
- Visit a local Contrada’s ceremonial space and museum.
- Join a traditional Contrada dinner the evening before the race.
- Stroll through San Gimignano, wander the “Town of Fine Towers".
- Go truffle hunting in Chianti forests with an expert and their trained dog.
Itinerary
32km | 560
Welcome to Italy and the start of an amazing adventure on and off the bike! The IBT team will be there to greet you and whisk you away to your charming hotel, tucked into the stunning Chianti hills.
Take a moment to relax while we get your bike ready for the week ahead. Then, join us for a gentle ride to shake off the travel and soak in your first taste of Italy, finishing with a lively aperitivo.
Enjoy dinner and local wines, meet fellow guests, and glimpse the week ahead in Tuscany.
Hotel Belvedere di Sanleonino | Castellina in Chianti
83 km | 1390 m
Today’s ride takes you to the stunning hilltop city of San Gimignano, a UNESCO World Heritage site. As a well-deserved reward for your climb, we’ll pause for a gelato in the “Town of Fine Towers,” soaking up the charm and history of this medieval gem.
Back at the hotel, unwind with a shower and some relaxation before enjoying a delicious regional dinner with the team, recharging for tomorrow’s scenic loop.
Hotel Belvedere di Sanleonino | Castellina in Chianti
63 km | 960 m
Today we ride to Siena, a city of quiet beauty and timeless charm. You’ll experience one of cycling’s most iconic roads - the Strade Bianche, Tuscany’s famous white gravel routes.
Roll through the stunning hills lined with cypress trees, soaking in the sweeping, majestic landscape as you ride.
In the evening, enjoy dinner in Siena with a local Contrada (community team), immersing yourself in the excitement and tradition of tomorrow’s Palio horse race - a once-in-a-lifetime adventure all in one trip.
Hotel Belvedere di Sanleonino | Castellina in Chianti
40 km | 250 m
Today offers a truly unforgettable experience as the contradas, tradition, and individual courage come together in Siena’s extraordinary medieval ritual - the Palio horse race.
This is no ordinary race; it’s a dramatic test of skill, strength, and community spirit, where both horse and rider face an astonishingly challenging course.
After the race, you’ll visit one contrada’s ceremonial space and museum, gaining an up-close look at the vibrant history and living traditions of the Palio.
Hotel Belvedere di Sanleonino | Castellina in Chianti
55 km | 850 m
Your day begins with a scenic Chianti loop by bike, winding through rolling hills, vineyards, and iconic cypress-lined roads. As you pedal through charming villages like Radda and Castellina in Chianti, you’ll soak in the stunning landscapes and the true essence of Tuscany.
In the afternoon, trade your bike for an unforgettable truffle-hunting adventure, guided by an expert and their trained dog. Stroll through fragrant oak forests, discover the secrets of this prized delicacy, and finish the day with a tasting of freshly foraged truffles paired with exquisite local wines.
Hotel Belvedere di Sanleonino | Castellina in Chianti
All good things must come to an end, and after an incredible few days of cycling, discovery, and unforgettable experiences, it’s time to bid farewell to Tuscany. Our team will be on hand to ensure a smooth departure, helping you with transfers and onward travel so you can leave with ease and comfort.
Dates & Prices
| Dates | Price | Availability | ||
|---|---|---|---|---|
| Mon 29 June - Sat 4 July | From €4999 |
|
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.
The nuts and Bolts
What's Included?
- 5 nights' in a 4* accommodation
- Transfer from/to Firenze Santa Maria Novella Train Station
- All breakfasts
- 2 dinners
- Water and coffee are complimentary during meals that are included in the package
- Vineyard tour and wine tasting
- VIP seating for the Palio di Siena
- Cerimonial dinner with Contrada
- Supported rides with snacks and water
- Bike Hire
- Truffle hunting
- Strade Bianche day
- IBT Gift Bundle
- GPX routes
- Bike cleaning service
- 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 cycling enthusiasts seeking an authentic Italian cultural experience.
- Total Kilometres: Approximately 270 km (167 miles) of scenic cycling through rolling hills, gravel roads, and charming towns.
- When: From 29th June to 4th July 2026.
- Start: The journey begins in Florence, with a transfer to our hotel Castellina in Chianti.
- Finish: From Castellina, a transfer will be arranged to take you back to Florence.
- Nearest Airport: We recommend looking into flights to Florence Airport (FLR), Bologna Airport (BLQ) or Roma Airport (FCO).
- Top Tip: Spaces are limited, so book early to secure your spot and guarantee access to this one-of-a-kind experience!
- Average Age of Guest:Age is no barrier - every cycling enthusiast eager for a new and authentic experience is welcome./li>
- Male vs Female %: Male and female participants are well balanced, making this tour ideal for friends, couples, and families.
| Where to Meet |
Please arrange to meet us at Florence Train Station (Santa Maria Novella) at 2 pm on day 1. We will contact you via WhatsApp in the days leading up to the start of your tour to confirm your transfer and the name of the staff member collecting you. |
|---|---|
| Drop off Location |
We can assist you with planning and booking of onward travel following the conclusion of your tour. We will run a morning transfer to Florence Train Station, 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 the train station to the hotel is around 45 minutes. |
| Road Conditions |
The general road conditions in Tuscany are very good. With a mix of smooth asphalt and rugged strade bianche, plus terrain from gentle slopes to challenging hills, the region offers stunning views and rewarding rides at every turn. |
| Cuisine |
Tuscany’s cuisine is a celebration of simple, fresh ingredients and traditional flavours. Known for its rustic dishes. Local produce, such as olive oil, truffles, and Pecorino cheese, play a key role, along with Tuscany’s famous Chianti wines. |
| Hotel Facilities |
The hotel on this tour have pool and we recommend bringing your swimming costume. Hotels also have laundry service, good WiFi and bar service. Hotels may charge extra to use some of these facilities. |
| Weather |
Our highly experienced local guides check the weather on a daily basis and amend rides accordingly - should there be a need. The average summer temperature in Tuscany can range from 20°C - 30°C (68°F - 86°F). |
| What Happens Next? |
Are you thinking about joining us? You probably have some questions! There are a number of ways to contact us. Email is best - we will reply within 24 hours. Please check your SPAM/JUNK folder should you not have received an email in this time. 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. |
Hotel
HOTEL BELVEDERE DI SAN LEONINO ★★★★
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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
