Day 1: Arrive to Florence. Transfer to Siena. Warm-Up Ride
Mid-morning greeting by our local guides and Sweet Skills coach at the Piazza Piave in Florence.
Transfer about 1 hour to the Pratomagno mountains, where we’ll get used to our bikes and test them (and our skills!) on some fun singletrack and doubletrack. After an après espresso, we’ll load the bikes and transfer to Siena, where we’ll spend our first two nights.
Overnight: Albergo Chiusarelli
Distance: 38 km, 1500 m descent
Day 2: Ride Chianti Classico Region. Explore Siena & Guided Walking Tour
Today we’ll ride through the famous Chianti region, weaving through oak forests, vineyards, and hilltop villages. After lunch in a classic Tuscan village, we’ll return to Siena for an afternoon to explore and enjoy a guided walking tour of the city.
Overnight: Siena Hotel
Distance: 60 km, 1400 m
Day 3: Ride to Hilltop Montalcino. Afternoon Brunello Wine Tasting
We ride south of Siena through soft rolling hills and panoramic views, eventually reaching the iconic hilltop town of Montalcino. In the afternoon, we’ll visit the Col di Lamo winery, renowned for its production of Brunello di Montalcino.
Overnight: Albergo Chiusarelli
Distance: 48 km, 900 m descent
Day 4: Transfer to Massa Marittima
This morning we say farewell to Siena and transfer to Massa Marittima, one of Tuscany’s top mountain biking destinations. This area is packed with hundreds of trails and natural terrain features — a true mountain bike paradise.
Overnight: Massa Marittima Hotel
Distance: 32 km, 1000 m

Day 5: Ride Capanne Trail Network
A relaxed pedal through vineyards and a short climb through cork forests brings us to the Capanne trail network. This bike park-style area features fast, flowy lines and rocky descents. A highlight is the “Canyon Trail”, full of berms and swoops — a rider favorite.
Overnight: Massa Marittima Hotel
Distance: 32 km, 1000 m
Optional: Possibility to extend the ride
Day 6: Transfer to the Mediterranean. Ride Tirli & Castiglione della Pescaia
A scenic morning transfer brings us to the coastal town of Castiglione della Pescaia, known for its medieval fortress and beach views. Today we ride cruisy singletrack with coastal panoramas. In the evening, enjoy sunset on the beach from our seaside hotel.
Overnight: Castiglione Hotel
Distance: 42 km, 1200 m
Optional: Possibility to extend the ride
Day 7: Ride Tirli & Castiglione della Pescaia
Our final day of riding keeps us close to the sea. We may visit the tiny, remote village of Tirli (population 284) and aim to end the ride at Cala Violina, one of Italy’s most beautiful beaches, famous for its “violin-sounding” sand.
Overnight: Castiglione Hotel
Distance: 52 km, 1400 m
Day 8: Transfer to Florence Airport
Morning transfer (2 hours) to Florence Airport (FLR).
Please book flights to depart no earlier than 12:00 PM. Alternatively, you may choose to stay overnight near the airport and fly out the following day.









LODGING AND CUISINE
CLIMATE
NOT INCLUDED


