A Curated Cycling Journey
Tuscany Heart is a refined cycling journey through the most authentic and iconic landscapes of Tuscany — from the silent forests of the Casentino Valley to the Renaissance beauty of Florence and the timeless elegance of Siena.
Designed for travelers who seek depth over distance, this experience blends scenic riding with curated wine estates, medieval hill towns, and boutique countryside hospitality.
Each stage reveals a different soul of Tuscany: hidden mountain roads, vineyard-covered hills, historic piazzas, and legendary white gravel routes.
This is not about reaching another city — it is about immersing yourself in the rhythm, beauty, and heritage of Tuscany itself.
Optional experiences may include:
The afternoon remains free to experience Florence at your own rhythm.
Tomorrow, the journey continues through the Tuscan hills toward Siena.
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.
Scenic ride through quiet forest roads, monasteries, and medieval villages in one of Tuscany’s most authentic regions. Afternoon at leisure. Private hands-on cooking class in the evening and convivial dinner at the villa.
A steady climb to Passo della Consuma through dramatic mountain landscapes, followed by a sweeping descent into Chianti’s vineyards. Private wine tasting and lunch at Tenuta Frescobaldi. Arrival in Fiesole overlooking Florence.
Relaxed panoramic ride through olive groves and Renaissance villas with sweeping views over Florence. Afternoon free to explore museums, boutiques, and historic cafés at your own pace.
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 legendary white gravel roads made famous by L’Eroica. Stop in Monteriggioni before a private wine experience and refined lunch at Castello di Brolio. Celebratory farewell dinner in the Tuscan countryside.
Breakfast at leisure and private transfer to Florence airport or train station.
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.
