From Hidden Corners of Tuscany to the Eternal City
Tuscany Heart is a curated cycling journey through the most evocative landscapes of Central Italy — a seamless blend of hidden countryside, Renaissance cities, world-class wines, and timeless culture.
From the quiet forests of the Casentino Valley to the vineyard-covered hills of Chianti, from Siena’s medieval grandeur to the ancient stones of the Appian Way, this experience is designed for travelers who seek more than distance and elevation.
Each day balances scenic riding with refined hospitality, immersive food and wine experiences, and boutique accommodations carefully selected for character and comfort.
It is not simply a route from Tuscany to Rome, it is an elegant progression through the very soul of Italy.
Arrive in Florence and enjoy a private transfer to the peaceful Casentino Valley. Check-in at Casale Chiesina and time to unwind in a serene countryside setting. A sunset aperitivo in the garden is followed by a refined welcome dinner, introducing the authentic flavors and spirit of Tuscany.
A scenic ride through quiet forest roads and timeless medieval villages in one of Tuscany’s most authentic regions. Afternoon at leisure, followed by a private hands-on cooking experience and a convivial dinner at the villa.
A rewarding climb through dramatic mountain landscapes to Passo della Consuma, followed by a sweeping descent into the rolling vineyards of Chianti. Private wine tasting and refined lunch at Tenuta Frescobaldi. Arrival in Fiesole, overlooking the timeless skyline of Florence.
A relaxed panoramic ride through olive groves and Renaissance villas, with sweeping views over Florence and its iconic skyline. Afternoon at leisure to explore the city at your own pace, wandering through art filled streets, refined boutiques, and historic cafés.
A point-to-point ride through the heart of Chianti, along vineyard-covered hills and cypress-lined roads.
Lunch in Certaldo, followed by a magical approach to the medieval towers of San Gimignano rising on the horizon. Overnight in a refined countryside estate, surrounded by timeless Tuscan landscapes.
Ride selected sections of the iconic white gravel roads made legendary by L’Eroica, immersed in the pure essence of Tuscan cycling heritage. Pause in Monteriggioni and Siena before a private wine experience and refined lunch at Castello di Brolio. A true celebration of Tuscany’s timeless cycling culture.
After several rewarding days across Tuscany’s forests, hills and legendary Strade Bianche,
today offers a refined pause in the heart of Siena.
No scheduled ride.
A scenic transition south toward the Eternal City. Arrival in Rome and check-in at a refined boutique hotel in the historic center. Evening at leisure to immerse yourself in the timeless Roman atmosphere, among illuminated monuments and elegant piazzas.
Ride along the ancient Appian Way, surrounded by Roman ruins and open countryside landscapes. Continue into the rolling hills of the Castelli Romani and enjoy a refined farewell lunch in Castel Gandolfo. Conclude your journey with a celebratory dinner in Rome — a fitting finale to an unforgettable Italian adventure.
Breakfast at leisure, savoring the final moments of your Italian journey. Private transfer to Rome airport or train station for your onward travels.
Guests may choose to skip any scheduled ride while continuing to enjoy the full program of the day.
This includes:
• Travel with the support vehicle
• Participation in all planned experiences (wine tastings, lunches, cultural visits)
• Arrival at the hotel together with the group
• Full access to property amenities
This option allows guests to recover physically without missing any of the curated lifestyle
experiences. Available on any riding day.
Guests may shorten the daily ride distance by using the support vehicle at any time.
This option offers:
• Flexible pick-up during the route
• Partial ride segments
• Customized distance adjustments
• Full participation in all scheduled activities
Ideal for guests who prefer a lighter effort on specific days.
In Florence and Siena, guests may choose a fully curated non-riding day.
Instead of cycling, guests may enjoy:
• Private guided cultural visits
• Museum fast-track entry
• Artisan workshops
• Cooking classes
• Spa and wellness time
• Private shopping experiences
• Extended relaxation at the hotel
All experiences are arranged to ensure reconnection with the group for evening activities.
This option transforms a rest day into a refined lifestyle experience.
This too fantastic Bike Tour can also be done on our exceptional Gravel bikes, classic or electric!
Our gravel bikes are ideal for navigating the diverse terrain of Casentino. Whether it’s paved roads, dirt trails, or hilly routes, gravel bikes offer the versatility and durability needed to enjoy every mile of our tour. With their sturdy construction and comfortable design, you’ll tackle every challenge with ease and style.
• Accommodation at Casale Chiesina
• All meals & beverages*
• One day Tuscany school cooking
• Personalized Castelli InGIRO jersey
• Rudy Project helmets
• Traditional, E-bikes, Gravel & E-Gravel bikes
• Support vans & private shuttles
• Laundry service for cycling clothing
• Bike mechanic & washing service
• Local expert trip leaders
• Daily planning & briefings
• Private guided visits (museums, wineries, historic sites),
• Special events as mentioned in the bike tour program.
• Hiking guides
*Extra drinks outside group activities or menus may incur additional charges.
