Tuscan Treasures: A Cycling Journey from Florence to Siena
Itinerary
Discover Tuscany’s rich tapestry of art, history, and flavor on a three-day ride from Florence to Siena. Pedal through Chianti vineyards, medieval villages, and the surreal Crete Senesi, where every mile blends Renaissance beauty with authentic Tuscan charm. A journey of iconic cities, hidden gems, and unforgettable experiences.
Highlights
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Pedal from Renaissance Florence to the medieval heart of Siena
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Explore charming Chianti villages and world-famous vineyards
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Discover the iconic Towers of Monteriggioni
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Marvel at Siena’s stunning Piazza del Campo
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Ride across the surreal landscapes of the Crete Senesi
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Conquer legendary climbs from Brolio Castle to Montalcino, immersing yourself in Tuscany’s art, history, and flavors
Day 1 - Welcome to Florence
Upon arrival in Florence, check in at your hotel and take some time to soak in the beauty of the Renaissance city. Wander through its charming streets, admire its iconic landmarks, and enjoy the vibrant atmosphere before beginning your cycling adventure. As part of your stay, you will also have tickets included for an independent visit to the world-famous Uffizi Gallery, where you can marvel at masterpieces by Botticelli, Leonardo da Vinci, Michelangelo, and many other great artists.
Torre dei Lari
Level 1 - Very easy
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Activity
Relax & DiscoverDay 2 - Florence to Radda in Chianti
Start your journey in the heart of Florence, surrounded by iconic Renaissance landmarks. As you leave the city, the scenic Chianti region unfolds with its rolling vineyards, medieval villages, and historic sites like the Certosa di Galluzzo monastery. Along the way, visit charming towns such as Greve and Panzano—famous for their authentic atmosphere, exceptional wines, and renowned culinary traditions. The day ends in Radda in Chianti, a medieval gem and the historic center of Chianti Classico wine production. Relax at your hotel with a glass of local Chianti wine, soaking in the timeless beauty and rich heritage of Tuscany. This is a journey that blends history, culture, and unforgettable flavors.
Palazzo Leopoldo Dimora Storica & Spa
Level 2 - Easy
56Km
Activity
Biking
Day 3 - Radda in Chianti to Siena
This unforgettable day of cycling takes you deep into the cultural and historical heart of Tuscany. Begin your journey among the medieval charm of Chianti, where hilltop villages like Castellina echo with centuries of Etruscan and Renaissance history. As you ride through sweeping vineyards and scenic landscapes, the region’s winemaking legacy and timeless beauty unfold around you. You'll pass through towns steeped in heritage, including Colle Val d’Elsa, famed for its crystal-making tradition, and Monteriggioni, a perfectly preserved 13th-century fortress that rises from the hills like a stone crown—unchanged since the days it inspired Dante.The day ends in Siena, one of Italy’s most iconic cities. With its Gothic architecture, winding alleys, and the striking Piazza del Campo, Siena offers the perfect finale—a place to unwind, explore, and reflect on a day filled with history, beauty, and the soul of Tuscany.
Hotel Athena
Level 3 - Moderate
70Km
Activity
BikingDay 4 - Siena Loop
Your final day begins in the heart of Siena, at the breathtaking Piazza del Campo—an architectural masterpiece and the iconic stage of the Palio horse race. Surrounded by Gothic splendor, the square sets the tone for a journey steeped in history and beauty. As you venture into the countryside, the echoes of Tuscany’s past accompany you—from the legendary 1260 Battle of Montaperti, immortalized by Dante, to the elegant charm of Castelnuovo Berardenga, the final outpost of Chianti Classico. The experience continues through serene villages and timeless landscapes, revealing hidden gems like Rapolano Terme, famed for its Roman-era thermal waters, and Asciano, a beautifully preserved medieval town rich in art and tradition. The day’s highlight is the stunning Crete Senesi—a dreamlike terrain of sculpted clay hills, winding ridgelines, and solitary cypress trees, offering one of Tuscany’s most iconic and surreal vistas. As you return to Siena, there's a moment to reflect on the beauty, heritage, and emotion of this three-day cycling adventure. The evening concludes with a celebratory dinner featuring classic Sienese dishes and local wines—an authentic taste of Tuscany to end an unforgettable journey.
Hotel Athena
Level 4 - Challenging
75Km
Activity
Biking
Day 5 - Arrivederci Siena!
Your journey ends in the stunning medieval city of Siena. After check-out, enjoy a last stroll through its winding alleys or a coffee in the famous Piazza del Campo before departing, taking home unforgettable memories of Tuscany.
Level 1 - Very easy
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Activity
Relax & DiscoverTrip wows
Set off on a three-day cycling adventure through Tuscany, from the artistic wonders of Renaissance Florence to the medieval beauty of Siena. Ride through vineyards, historic villages, and rolling hills, while discovering the region’s rich history, world-class wines, and timeless cultural experiences.
Cycling Through Florence’s Renaissance Icons
Embark on an unforgettable ride through Renaissance Florence, where you'll pedal past iconic landmarks like Brunelleschi’s magnificent dome, the Baptistery’s golden doors, and other historic treasures that define this timeless city!
Taste the Flavors of Tuscany
Immerse yourself in the heart of Tuscany’s rich culinary heritage, where every meal, vineyard visit, and village stop is an opportunity to savor the region’s exceptional flavors, from traditional dishes to world-renowned wines, all steeped in centuries of history and local tradition.
Monteriggioni & Siena: Timeless Architectural Marvels
Wander through the enchanting medieval streets of Monteriggioni, a town famed for its striking towered walls that have inspired poets like Dante across the centuries. From there, journey onward to the magnificent city of Siena, where the breathtaking beauty of Piazza del Campo awaits—an architectural gem that has stood the test of time, embodying the city’s deep historical roots and offering a remarkable fusion of art, culture, and enduring elegance in a truly unforgettable setting.
Discover the Enchanting Chianti Region
Set off on a scenic adventure through the legendary Chianti region, cycling along cypress-lined roads that weave through lush vineyards, sprawling olive groves, and charming medieval villages like Greve and Panzano, each offering a unique glimpse into Tuscany's rich heritage and breathtaking landscapes!
hotels
Please note that accommodations may vary based on availability.
Torre dei Lari
Torre dei Lari Residenza d’Epoca is a historic villa nestled in the peaceful hills near Florence, offering a perfect retreat for cycling enthusiasts. Guests can relax in elegantly furnished rooms, enjoy the outdoor pool and garden, and recharge before exploring the scenic Tuscan countryside by bike.
Hotel level
Premium
Plus
Pool, Restaurant, Parking
Palazzo Leopoldo Dimora Storica & Spa
Palazzo Leopoldo is a historic hotel nestled in the heart of Radda in Chianti. Housed in a 13th-century noble residence once frequented by Grand Duke Leopold II, it seamlessly blends medieval charm with modern luxury. Guests can unwind in elegantly appointed rooms featuring original frescoes and terracotta floors, indulge in traditional Tuscan cuisine at the renowned La Perla del Palazzo restaurant, and rejuvenate at the exclusive Spa Vignavecchia. Whether you're savoring local wines on the panoramic terrace or exploring the picturesque Chianti hills, Palazzo Leopoldo offers an unforgettable Tuscan retreat.
Hotel level
Premium
Plus
SPA, Pool, Restaurant
Hotel Athena
A charming 4-star hotel nestled within the historic walls of Siena, just a short walk from the iconic Piazza del Campo. Offering panoramic views of the Tuscan countryside, the hotel combines modern comfort with traditional Tuscan hospitality. Guests can enjoy elegantly furnished rooms, a rooftop terrace, and a renowned restaurant serving local cuisine. Hotel Athena provides a welcoming base for exploring the heart of Tuscany.
Hotel level
Quality
Plus
Restaurant, ParkingImportant info
- 4 nights accommodation in charming hotels or guesthouses (double occupancy)
- 4 breakfasts and 1 dinner featuring local cuisine
- Living Roads Kit: cycling cap and water bottle
- Helmet, Pedals and all necessary chargers and pump
- Daily luggage transfer between accommodations
- Detailed GPS routes
- Welcome briefing and orientation by a local representative
- Emergency phone support during the tour
- Secure bike storage at each overnight location
- Access to the Ride with GPS navigation app
- E-bike or premium road bike rental included for the entire tour (feel free to bring your own bike if you prefer)
- Uffizi Gallery ticket (one per person)
- Wine tasting experience with local Tuscan labels in an exclusive historic setting in Radda in Chianti
- Private Siena Guided Walking Tour with a licensed local guide
- Private guide for the entire duration of the tour
- Single room supplement
- E-Bikes supplement
- Additional gears
- Travel insurance (highly recommended). See our protection plan here.
- Airfare or transportation to/from the tour start and end locations
- Private transfer on first and last day from/to the nearest train station or airport
- Lunches and dinners not specified in the inclusions
- Personal expenses (e.g., souvenirs, drinks, snacks)
- Optional activities or excursions not mentioned in the itinerary
- Gratuities for drivers or hotel staff
- Additional nights of accommodation before or after the tour dates
Included
- 4 nights accommodation in charming hotels or guesthouses (double occupancy)
- 4 breakfasts and 1 dinner featuring local cuisine
- Living Roads Kit: cycling cap and water bottle
- Helmet, Pedals and all necessary chargers and pump
- Daily luggage transfer between accommodations
- Detailed GPS routes
- Welcome briefing and orientation by a local representative
- Emergency phone support during the tour
- Secure bike storage at each overnight location
- Access to the Ride with GPS navigation app
- E-bike or premium road bike rental included for the entire tour (feel free to bring your own bike if you prefer)
- Uffizi Gallery ticket (one per person)
- Wine tasting experience with local Tuscan labels in an exclusive historic setting in Radda in Chianti
- Private Siena Guided Walking Tour with a licensed local guide
Not included
- Private guide for the entire duration of the tour
- Single room supplement
- E-Bikes supplement
- Additional gears
- Travel insurance (highly recommended). See our protection plan here.
- Airfare or transportation to/from the tour start and end locations
- Private transfer on first and last day from/to the nearest train station or airport
- Lunches and dinners not specified in the inclusions
- Personal expenses (e.g., souvenirs, drinks, snacks)
- Optional activities or excursions not mentioned in the itinerary
- Gratuities for drivers or hotel staff
- Additional nights of accommodation before or after the tour dates
Definitely. If you prefer to ride with your own pedals (e.g., SPD, Look, flat), saddle, or helmet, just let us know when booking. We’ll have your bike ready to accommodate your personal gear upon arrival.
Yes, you’re welcome to use your own GPS device. Most of our bikes are compatible with GPS mounts. If you'd like to have a mount installed, please let us know in advance, mounts are available upon request for an additional fee. We’ll make sure it’s properly set up so you're ready to navigate with confidence.
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Why Living Roads?
OUR LOCAL TOUCH
As locals, we create journeys inspired by the way we live. Enjoy the best of Italian Roads and Hospitality with our expertise of more than 50 years as a tour operator.
FOR EVERYONE
Our tours are open to everyone, with different levels of difficulty. They’re never meant to be a race, but rather a chance to embrace the slow joy of discovery.
Culture you can taste
Cycling means earning every view and every bite. Our tours include regional wine tastings, cooking class, countryside dinners, and food experiences you’ll remember forever.
CURATED ACCOMODATIONS
Our selection of hotels is guided by the desire to promote local businesses and historic palaces or buildings, creating the perfect blend of authenticity and charm.
ASSISTANCE
You’ll never be alone on the road. You can always count on our remote support during the Self-Guided tours, or on the expertise of our local guides during the guided or joinable tours.
Meaningful miles
We ride slow and smart: our tours are designed to support local communities and reduce environmental impact for a way of traveling that feels as good as it looks.