Umbria to Tuscany: Bartali’s Legendary Route
Itinerary
Embark on an unforgettable cycling journey from Assisi to Florence, tracing the heroic path of Gino Bartali. This adventure blends Italy's rich history, breathtaking landscapes, and exceptional cuisine, making it perfect for cycling enthusiasts and history lovers alike.
Start in Assisi, pedaling through Umbria's rolling hills and peaceful backroads into the picturesque Tiber Valley. Continue past olive groves and vineyards to the serene shores of Lake Trasimeno before reaching Cortona, a Tuscan hilltop gem known for its medieval streets and authentic local cuisine.
From Cortona, ride deeper into Tuscany through the famed Chianti region, with its cypress-lined roads and sprawling vineyards, before arriving in Gaiole in Chianti for a relaxing evening of fine wines and Tuscan flavors. Conclude your journey in Florence, climbing to Piazzale Michelangelo for a breathtaking view of the city before celebrating its art, history, and culture.
Highlights
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Ride the legendary route of Gino Bartali
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Cross two iconic regions: Umbria and Tuscany
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Explore hidden gems like Cortona and Gaiole in Chianti, steeped in history and authenticity
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Savor Italy’s finest flavors with farm-to-table meals, Chianti wines, and local specialties along the way
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Finish with a panoramic climb to Piazzale Michelangelo, descending into the heart of the Renaissance
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Cycle through rolling hills, olive groves, and vineyard-lined roads, experiencing Italy’s landscapes, culture, and cycling heritage
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Day 1 – Warm-Up Ride & Assisi Discovery
Today’s ride is a gentle warm-up through the Umbrian countryside, starting from the Hotel Valle di Assisi and heading toward the charming town of Spello. The route winds through flat plains and olive groves, with some scenic gravel sections, before continuing toward Assisi. Along the way, enjoy a coffee break in Spello and take in its stunning hilltop views.
As you approach Assisi, admire the distant silhouette of the Basilica of San Francesco before returning through the valley to Santa Maria degli Angeli and back to the hotel.
In the late afternoon, join a private guided visit to the Basilica of Saint Francis of Assisi, where you’ll explore one of Italy’s most sacred sites and discover its extraordinary frescoes and spiritual atmosphere.
The evening is yours to relax at the hotel and reflect on your first day of adventure in Umbria.
Valle di Assisi Hotel Resort & SPA
Level 1 - Very easy
35Km
Activity
BikingDay 2 - Assisi to Cortona
Today’s ride takes you deep into the heart of Umbria, along peaceful backroads lined with vineyards, olive groves, and rolling hills. After leaving Assisi, enjoy gentle climbs and scenic descents, pausing in quiet villages for a coffee break and a taste of local life.
As you approach Lake Trasimeno, the landscape opens to stunning views where history and beauty meet — the site of Hannibal’s legendary victory. Ride along tranquil shoreline paths and stop for a lakeside lunch before continuing toward Passignano sul Trasimeno and Terontola, where a monument honors cycling hero Gino Bartali.
The day concludes with the iconic climb to Cortona — a rewarding ascent leading to one of Tuscany’s most charming hilltop towns. Explore its medieval streets, soak in the views, and celebrate a day filled with nature, history, and cycling passion.
Hotel San Luca
Level 4 - Challenging
87Km
Activity
Biking
Day 3 - Cortona to Gaiole
Today’s stage is the most demanding and exhilarating of the journey — a true cyclist’s dream through Tuscany’s rolling landscapes. The day begins with a sweeping descent from Cortona into tranquil countryside and canal paths before the terrain gradually rises again.
A long, scenic climb leads you back into Tuscany at Palazzolo, followed by a rewarding descent and a traditional lunch stop in a classic trattoria. The challenge continues as you enter the Chianti region, where winding roads lined with vineyards and cypress trees capture the essence of Tuscany.
Passing Castelnuovo Berardenga, you’ll reach Madonna di Brolio and the legendary Eroica Bar, a symbolic stop for cycling enthusiasts. A final gentle descent brings you to Gaiole in Chianti, birthplace of the Eroica ride — the perfect place to rest and celebrate a day of effort, beauty, and cycling heritage.
Paradiso in Chianti
Level 4 - Challenging
82Km
Activity
BikingDay 4 - Gaiole to Florence
Your final ride leads you through the heart of the Chianti region and into the cradle of the Renaissance, Florence. Pedal along rolling vineyard-lined hills and pass through charming villages like Radda, Panzano, and Greve in Chianti, perfect for a scenic pause or a coffee in a sunlit piazza.
After a final climb to Impruneta, the landscape shifts as you approach Florence. The route winds past elegant villas and stone walls, culminating at Piazzale Michelangelo, where breathtaking views of the Duomo and Arno River mark your triumphant arrival.
A celebratory descent into the city’s historic center brings your unforgettable Tuscan cycling adventure to a perfect close.
Torre dei Lari
Level 3 - Moderate
64Km
Activity
Biking
Day 5 - Arrivederci Tuscany!
Start your day in Florence with a relaxed breakfast at your hotel, taking in the early morning atmosphere of this Renaissance city. Once refreshed, step outside and enjoy a leisurely stroll through the charming streets of Florence. From world-famous landmarks to tucked-away corners, the city invites you to explore its rich history, art, and architecture at your own pace.
When it’s time for lunch, choose a local restaurant that catches your eye—Florence is known for its exceptional cuisine, from traditional Tuscan dishes to contemporary Italian flavors. Savor the experience and reflect on the beauty of the city around you.
As the afternoon unfolds, it will soon be time to say goodbye to Florence, carrying with you memories of its timeless elegance and vibrant culture.
Level 1 - Very easy
Activity
Relax & DiscoverTrip wows
Get ready for a journey filled with unforgettable highlights. From historic routes and scenic landscapes to exceptional cuisine and iconic destinations, these Trip Wows capture the essence of what makes this cycling adventure from Assisi to Florence truly extraordinary.
Ride in the Tracks of a Legend
Follow the heroic route of Gino Bartali, the Tour de France champion and World War II resistance figure who secretly transported documents to save lives—experience history with every turn of the pedal.
Tuscany’s Greatest Hits on Two Wheels
Cycle through postcard-perfect landscapes, from the golden hills of Umbria to the vine-draped slopes of Chianti—cypress-lined roads, medieval towns, and serene lake shores included.
A Culinary Ride Through Italy
Savor the flavors of Italy at every stop—Umbrian truffle dishes, Cortona’s rustic fare, Chianti’s celebrated wines, and a Florentine finale rich in both cuisine and culture.
The Grand Florence Finale
End your adventure with a climb to Piazzale Michelangelo for sweeping views over Florence’s skyline—an unforgettable moment that perfectly blends achievement, beauty, and history.
hotels
Please note that accommodations may vary based on availability.
Valle di Assisi Hotel Resort & SPA
Set in the heart of the Umbrian countryside just minutes from Assisi, Hotel Valle di Assisi is a welcoming 4-star resort offering beautiful panoramic views of Monte Subasio and the surrounding valley. Elegant rooms feature classic style, modern comforts, and many include terraces or private wellness areas. Guests can enjoy a scenic breakfast, relax at the spa, and explore the spacious grounds. With its peaceful setting and genuine hospitality, Hotel Valle di Assisi is the perfect base for discovering Umbria.
Hotel level
Premium
Plus
SPA, Pool, Parking, Gym
Hotel San Luca
Set just steps from Cortona’s historic center, Hotel San Luca is a welcoming 4-star retreat offering stunning panoramic views over the Valdichiana Valley and Lake Trasimeno. Elegant rooms feature classic decor, modern comforts, and many include balconies or spa baths. Guests can enjoy a rooftop breakfast and secure bike storage. With its central location and warm hospitality, Hotel San Luca is the perfect base for exploring Tuscany!
Hotel level
Quality
Plus
Parking, Gym
Paradiso in Chianti
Paradiso in Chianti is an elegant, family‑run hotel nestled in the heart of Gaiole in Chianti, Tuscany. Housed in a recently renovated historic palazzo, it blends traditional Tuscan charm with contemporary comfort . The property overlooks the town square and is just steps from local cafés, wine bars, and restaurants — yet offers a peaceful retreat. Paradiso in Chianti is a favorite spot for cyclists on the famed Eroica route!
Hotel level
Quality
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
- 5 nights accommodation in charming hotels or guesthouses (double occupancy)
- 5 breakfasts, 1 lunch, 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
- Access to the Ride with GPS navigation app
- Welcome briefing and orientation by a local representative
- Emergency phone support during the tour
- Secure bike storage at each overnight location
- E-bike or premium road bike rental for the entire tour (feel free to bring your own bike if you prefer)
- Guided tour of the Basilica of Assisi, with round-trip transportation from your hotel
- Wine tasting at a selected winery in Cortona
- Cooking class at a renowned cooking school in the Chianti region, with round-trip hotel transportation
- Heart of Florence walking tour with a licensed local guide (shared tour — private option available on request)
- 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
- 5 nights accommodation in charming hotels or guesthouses (double occupancy)
- 5 breakfasts, 1 lunch, 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
- Access to the Ride with GPS navigation app
- Welcome briefing and orientation by a local representative
- Emergency phone support during the tour
- Secure bike storage at each overnight location
- E-bike or premium road bike rental for the entire tour (feel free to bring your own bike if you prefer)
- Guided tour of the Basilica of Assisi, with round-trip transportation from your hotel
- Wine tasting at a selected winery in Cortona
- Cooking class at a renowned cooking school in the Chianti region, with round-trip hotel transportation
- Heart of Florence walking tour with a licensed local guide (shared tour — private option available on request)
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
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 range from easy to moderate and are suitable for a wide range of fitness levels. You don’t need to be an athlete, whether you’re a beginner or a more experienced cyclist or hiker, we have options tailored to your ability and pace. E-bike rentals are also available for extra comfort on selected routes. Not sure which adventure suits you best? Check out our Activity Levels to find your perfect fit.
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.
Trips can be booked exclusively by contacting our team directly. We’re happy to assist you via email or phone and will guide you through every step of the booking process.
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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.