Tuscany Heart – From Casentino to Florence, Pisa and Lucca
An Intimate Cycling Experience
The Secret Tuscany Ride is an intimate cycling journey through the lesser-known soul of Northern Tuscany — a land of quiet forests, winding mountain passes, vineyardcovered hills, and timeless walled cities.
Beginning in the peaceful Casentino Valley and concluding within the Renaissance walls of Lucca, this experience is designed for riders who value authenticity, rhythm, and refined simplicity over crowds and spectacle.
Each day unfolds along scenic secondary roads, paired with boutique countryside stays, curated wine experiences, and the warmth of genuine Tuscan hospitality.
It is not the Tuscany everyone sees, it is the Tuscany few truly discover.
Arrival in Florence and private transfer to the peaceful Casentino Valley. Check-in at Casale Chiesina, surrounded by nature and panoramic views. Sunset aperitivo in the garden followed by a refined welcome dinner featuring seasonal Tuscan flavors.
A scenic ride through quiet secondary roads, chestnut forests, and medieval hamlets far from the crowds.
In the afternoon, enjoy a private hands-on cooking class with a local chef, followed by a convivial dinner at the villa.
Climb through forested mountain roads to Passo della Consuma before descending into Chianti’s vineyard landscapes. Private wine tasting and lunch at Tenuta Frescobaldi.
Arrival at a boutique hotel in Fiesole overlooking Florence.
A relaxed panoramic ride through olive groves and Renaissance villas surrounding Florence. Afternoon at leisure to explore the city’s art, boutiques, or cafés. Dinner at a carefully selected traditional trattoria.
Transfer to Lucca and check-in at a boutique hotel within the Renaissance walls. Enjoy an easy ride along the historic city walls and surrounding countryside. Evening free to discover Lucca’s elegant piazzas and restaurants.
Final ride through vineyards, olive groves, and the lush hills of Garfagnana framed by mountain views. Farewell countryside lunch followed by a celebratory dinner in Lucca’s historic center.
Breakfast at leisure and private transfers to Pisa or Florence.
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.
