Tuscany and Umbria on Two Wheels: An Epic Gravel Bike Adventure

Discover Italy on two wheels, your gravel paradise is awaiting for you!

Imagine pedaling through the heart of Italy, where ancient history, breathtaking landscapes, and culinary delights converge into an unforgettable journey. At Out of the Box Florence, we pride ourselves on creating bike tours that break away from the conventional—offering you an experience as unique and adventurous as the landscapes you traverse. Our latest gravel bike itinerary connects the legendary towns of Florence, Siena, Cortona, Perugia, and Assisi, all while riding on scenic gravel roads and quiet secondary paths that reveal the true soul of Tuscany and Umbria.

A Journey Designed for Every Adventurer

This route was crafted to challenge even the most seasoned cyclists while welcoming those who appreciate a more relaxed pace. Our adventure was successfully completed as a dynamic 3-day tour for riders with a robust level of fitness. For those who prefer a leisurely exploration of Italy’s hidden gems, we offer an adaptable version that stretches to 5 days or more—allowing you ample time to pause, savor local flavors, and truly soak in the beauty of every stop.

The Itinerary: A Tale of History, Culture, and Culinary Wonders

Day 1: From Florence to Siena

Your journey begins in the enchanting city of Florence, a melting pot of art, culture, and Renaissance marvels. As you leave behind the urban buzz, you’ll ride through rolling hills, olive groves, and sunlit vineyards that epitomize the Tuscan countryside.

• Culinary Highlight: Enjoy a hearty start with a traditional Florentine breakfast and later indulge in the region’s famed dishes—think rich pasta sauces and a glass of Tuscan red wine.

Day 2: Siena and the Evening Charm of Cortona

Departing from Siena, known for its medieval streets and vibrant local life, your ride continues along ancient roads that trace centuries of history. As the day unfolds, you’ll be treated to panoramic views of rustic farmlands and historic villages.

• Evening Stop – Cortona: As day 2 winds down, the itinerary leads you to Cortona—a hidden gem tucked away in the rolling hills of Tuscany. Here, you can enjoy the town’s timeless charm, wander its quaint streets, and witness a beautiful sunset over the landscape.

Day 3: A Scenic Passage Through Perugia to Assisi

Your final day is the crescendo of this epic adventure. Departing from Cortona in the morning, you set off on the final stretch of your journey.

• Perugia – A Quick Glimpse: As you ride, you will pass through Perugia. Rather than a full stop in the old town, this leg of the route offers a fleeting glimpse of Perugia’s vibrant surroundings, allowing you to experience its energy without the detour into its historic center.
• Destination – Assisi: The ride culminates in the serene town of Assisi, a place renowned for its spiritual heritage and artistic splendor. Here, you can relax, reflect on your journey, and savor a final meal featuring Umbrian culinary traditions paired with exquisite local wines.
• Culinary Highlight: Throughout the day, each region offers you a taste of its signature dishes—from artisanal cheeses and cured meats to fresh, handcrafted pastas—each complemented by the finest local vintages.

Tailored to Your Pace and Passion

At Out of the Box Florence, we understand that every rider’s journey is personal. Whether you opt for the energetic 3-day tour or choose to extend your adventure over 5 days or more, our itinerary is designed with flexibility in mind:

• 3-Day Adventure: Perfect for thrill-seekers eager to experience a fast-paced, immersive journey.
• Extended Itinerary (5+ Days): Ideal for those who wish to linger over each destination, explore additional local attractions, and truly savor the culinary and cultural delights along the way.

Our carefully curated routes and flexible scheduling ensure that every cyclist, regardless of fitness level or pace, will discover joy and wonder on these historic roads.

The Local Experience: More Than Just a Bike Tour

Beyond the thrill of the ride, our tour is a celebration of the region’s rich cultural and gastronomic heritage:

• Expert Guides: Our local guides are passionate about sharing insider knowledge of Tuscany and Umbria. Their expertise will enhance your experience with fascinating stories, local legends, and hidden spots off the beaten path.
• Quality Bike Rentals & Accommodations: Forget the hassle of logistics. We offer top-of-the-line bike rentals and handpicked accommodations—from charming bed and breakfasts to boutique hotels—that provide comfort and local flair.
• Culinary & Wine Delights: Along every stretch of your journey, indulge in authentic Italian cuisine. Sample local dishes and raise a glass of fine wine at each stop, ensuring your journey is as delightful to the palate as it is exhilarating for the soul.

Embrace the Adventure with Out of the Box Florence

This gravel bike adventure is more than just a ride—it’s a journey into the very heart of Italy. With each pedal stroke, you’re not only covering miles but also uncovering layers of history, culture, and culinary excellence. From the Renaissance allure of Florence to the sacred serenity of Assisi, this tour is your passport to an experience that is as enriching as it is unforgettable.

Are you ready to redefine your idea of adventure? Explore our detailed itinerary and discover more unique bike tours at Out of the Box Florence. For further inquiries or to book your next adventure, please visit our Contact Page.

Curious to see the full collection of routes and inspiring details? Check out our meticulously crafted route collection on Komoot: Florence to Assisi – Passing by Siena and Cortona.

Embrace the challenge, indulge in the flavors, and experience Italy like never before—one gravel road at a time.