Renaissance Ride: from Siena to the Heart of Florence
Itinerary
Cycle from the medieval beauty of Siena to the Renaissance heart of Florence on a four-day journey through Tuscany’s most iconic landscapes. Ride through the rolling hills of Chianti, explore historic wine estates and hilltop villages, and immerse yourself in the rich culture, cuisine, and heritage of the region. More than a cycling tour, this is a ride through centuries of art, tradition, and timeless beauty—Tuscany at its most authentic.
Highlights
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Pedal from Siena to Florence through the Heart of Tuscany
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Ride Cypress-Lined Roads Across the Vineyards of Chianti
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Discover the Legendary L’Eroica Heritage in Gaiole in Chianti
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Explore Medieval Villages and Tuscany’s Timeless Landscapes
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Climb to Florence’s Panoramic Heights for a Grand Finale
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Immerse Yourself in Tuscany’s Culture, Cuisine, and Timeless Beauty
Day 1 - Siena Warm Up
Our journey begins in the captivating city of Siena, a medieval masterpiece and UNESCO World Heritage site. Renowned for its 17 historic Contrade and its enduring rivalry with Florence, Siena offers a powerful introduction to the soul of Tuscany. From the heart of the city, we step into the iconic Piazza del Campo, one of the most beautiful medieval squares in the world and home to the legendary Palio horse race. Surrounded by the graceful lines of the Palazzo Pubblico and the soaring Torre del Mangia, the square evokes centuries of civic pride and tradition. Enjoy a guided tour of Siena, exploring its rich history, hidden corners, and timeless landmarks with a local expert. As we leave Siena behind, the landscape opens into the rolling hills and quiet beauty of the Sienese countryside. This region is steeped in history, from the medieval legacy of rival city-states to the timeless rhythm of rural life. Every vista and village speaks to Tuscany’s rich cultural tapestry, offering a perfect prologue to the days ahead.
Hotel Athena
Level 1 - Very easy
30Km
Activity
BikingDay 2 - Siena to Radda in Chianti
Our second day begins with a final glimpse of Siena’s medieval beauty before we roll into the open countryside. In Montaperti, the landscape whispers tales of ancient battles, while Castelnuovo Berardenga welcomes us with its peaceful charm and deep Sienese roots. As we enter Chianti, the landscape becomes a painter’s dream...rolling hills, olive groves, cypress-lined roads, and endless rows of vineyards. Each turn reveals a new vista, each village a story. A highlight of the day is our stop at Caffè Eroica, a beloved landmark for cyclists around the world. From there, we continue through the wine-rich lands of Madonna a Brolio and Gaiole in Chianti, where the spirit of L’Eroica lives on. The final ascent to the hilltop abbey of Badia a Coltibuono is both challenging and unforgettable. The day concludes in Radda in Chianti, a charming medieval town in the heart of the region. In the evening, take part in a hands-on cooking class, discovering the secrets of traditional Tuscan cuisine before enjoying a delightful dinner featuring your own creations.
Palazzo Leopoldo Dimora Storica & Spa
Level 2 - Easy
55Km
Activity
Biking.webp)
Day 3 - Radda in Chianti Loop
Today’s journey immerses you in the heart of Chianti Classico, beginning in the medieval town of Radda. As you ride through this iconic wine region, you’ll explore ancient hilltop villages like Castellina in Chianti, once an Etruscan stronghold and now famed for its fortress and atmospheric stone tunnels. The route winds through a landscape of vineyards and woodlands shaped by the historic Pesa River, revealing the agricultural soul of Chianti. A highlight of the day is the celebrated village of Panzano, home to the legendary butcher Dario Cecchini—an icon of Tuscan culinary tradition whose passion for meat and theatrics has gained worldwide fame. From there, you'll discover Montefioralle, one of Tuscany’s most beautiful medieval hamlets, perfectly preserved and perched above the Chianti hills. With its cobbled lanes and panoramic views, it feels like stepping into a Renaissance painting. The day continues in Greve in Chianti, a lively market town with a distinctive triangular piazza, ideal for enjoying local flavors and artisanal culture. Rich in history, tradition, and unforgettable scenery, this stage of the Renaissance Ride offers a full immersion into the essence of Tuscany. Back at the hotel, unwind with a wine tasting featuring local Chianti vintages—a perfect way to toast your day’s ride.
Palazzo Leopoldo Dimora Storica & Spa
Level 3 - Moderate
65Km
Activity
BikingDay 4 - Radda in Chianti to Florence
As the journey continues through the heart of Chianti, the landscape evolves into a rich tapestry of vineyards, valleys, and timeless hilltop towns. Along the way, you’ll encounter charming villages that blend rustic beauty with authentic Tuscan character—perfect for a pause to savor a local coffee or simply take in the surroundings. The day’s highlight is a rewarding ascent to Impruneta, a town steeped in history and famed for its terracotta artistry that has shaped some of Florence’s most iconic architecture. This climb is not just a physical challenge, but a symbolic gateway to the grandeur that awaits. Approaching Florence, the scenery subtly shifts—ancient villas, olive groves, and Renaissance echoes mark your entry into one of the world’s most culturally rich cities. The journey reaches its spectacular crescendo at Piazzale Michelangelo, where sweeping views of Florence, the Arno River, and Brunelleschi’s dome unfold beneath you. This is more than a finish line—it’s a celebration of everything the Renaissance Ride embodies: history, effort, beauty, and the enduring magic of Tuscany.
Torre dei Lari
Level 2 - Easy
55Km
Activity
Biking
Day 5 – The Last Sip: A Day to Savor the Journey
Your final day begins with a private guided visit to Florence’s Galleria dell’Accademia, where you’ll stand before Michelangelo’s David and explore other masterpieces of the Renaissance in an intimate, inspiring setting. It’s a moment to immerse yourself in Florence’s artistic soul before the day unfolds.
Afterward, enjoy a gentle pause — no bikes, no rush, just time to soak in the spirit of Tuscany. Bask in the sun and look back on the rolling hills, historic villages, and unforgettable moments you’ve experienced.
It’s the perfect way to let the journey sink in before you say goodbye.
Level 1 - Very easy
Activity
Relax & DiscoverTrip wows
Ride through Tuscany’s soul on a four-day journey from Siena to Florence, where every turn reveals medieval towns, vineyard-covered hills, and centuries of art and culture. From the iconic Piazza del Campo to the panoramic heights of Piazzale Michelangelo, The Renaissance Ride blends world-class cycling with unforgettable Tuscan flavors, heritage, and scenery.
Cycle from Siena’s Piazza del Campo to Florence’s Piazzale Michelangelo
Begin your ride in the heart of Siena’s historic center and finish with panoramic views over Florence — a journey between two of Italy’s most iconic cities.
Ride through the iconic vineyards and villages of Chianti Classico
Pedal through the postcard-perfect hills of Chianti, passing terraced vineyards, olive groves, and centuries-old villages rich in character and charm.
Discover the cycling legacy of L’Eroica in Gaiole in Chianti
Feel the spirit of vintage cycling on the white roads of Gaiole, birthplace of L’Eroica and a symbol of Tuscany’s deep-rooted passion for the sport.
Explore medieval gems like Montefioralle, Radda, and Castellina in Chianti
Wander cobbled streets, admire stone towers, and enjoy sweeping views in some of Tuscany’s most authentic and picturesque hilltop towns.
Taste world-class wines and traditional Tuscan cuisine at historic estates
Savor the best of Chianti Classico with tastings at family-run wineries and meals featuring local specialties rooted in Tuscan tradition.
Experience the artistic grandeur of Florence and its Renaissance skyline
Arrive in Florence in true style, with a breathtaking descent into the city’s artistic heart—home to Michelangelo, Brunelleschi, and timeless masterpieces.
hotels
Please note that accommodations may vary based on availability.
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, 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
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, ParkingImportant info
- 4 nights accommodation in charming hotels or guesthouses (double occupancy)
- 4 breakfasts, 1 lunch and 2 dinners 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)
- Private Siena Guided Visit with a professional guide
- Wine tasting experience with local Tuscan labels in an exclusive historic setting in Radda in Chianti
- Cooking class at a renowned cooking school in the Chianti region, with round-trip hotel transportation
- Private Accademia Gallery Guided Visit with a professional 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 (if applicable)
- 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, 1 lunch and 2 dinners 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)
- Private Siena Guided Visit with a professional guide
- Wine tasting experience with local Tuscan labels in an exclusive historic setting in Radda in Chianti
- Cooking class at a renowned cooking school in the Chianti region, with round-trip hotel transportation
- Private Accademia Gallery Guided Visit with a professional 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 (if applicable)
- 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
You’ll receive detailed GPS routes, accommodation info, and remote support. Follow the route at your own pace, with full independence but peace of mind.
Our tours, both Self-Guided and Full Supported, are ideal for solo travelers.If you choose a Self-Guided experience, you’ll enjoy the freedom of independent travel with the reassurance of our reliable remote support whenever you need it.
Prefer a Full Supported tour? You’ll join a welcoming group of like-minded travelers and be accompanied by expert local guides ready to assist you throughout the journey. Whether you’re riding, hiking, or sharing a meal, you’ll always find connection and shared moments.Traveling solo doesn’t mean being alone, it means choosing your own pace while being part of something meaningful.
Yes, you’re welcome to use your own bike. It must be in excellent mechanical condition and suitable for the route you’ve chosen. For safety and logistical reasons, we kindly ask you to contact us in advance to confirm whether we can accommodate the transport and storage of your bike before completing your booking.
Yes. Before your tour, we’ll request your sizing details (height, inseam, etc.) to prepare your bike. Upon arrival, we’ll make final adjustments to ensure an optimal and comfortable fit for your multi-day ride.
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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.