May 2-9, 2026
Tuscany, italy
25- 35 miles daily
6 Days
7 Nights
10 person Group Max
Skill Level Intermediate
$5200 per person
$5700 single room supplement
We have dialed in our Tuscany gravel trip for the coming years and hope you can join us in 2025 and beyond. The tour starts in the historical village of San Quirico d’ Orcia where we’ll stay in a well appointed hotel for two nights. From here we’ll ride north to our next destination of Castelnuovo Berardenga. Located in the southern end of the world famous Chianti region it’s a real hidden gem and true locals village. We stay two nights here in a quaint renovated farm turned family run Agritourismo B&B. Continuing north we conclude our time in Chianti with two more nights in Radda in Chianti located in the heart of the region. Our last day we ride through the Tuscan hills into the historical walled city of Siena and finish in the Piazza del Campo, home to the world famous Palio di Siena horse race. We’ll enjoy a final dinner and say farewell before travels to points beyond.
Trip Overview
-
The group will be picked up in Siena at 3:00 by our guides and transferred to our historic hotel in San Quirico d'Orcia. At dinner we will go over the itinerary and logistics for the week and answer any questions that arise.
-
Loop ride in Val di Orcia on classic L’ Eroica di Montalcino roads. Return to our hotel.
-
Today we pack up our bags for transport. We will ride a mix of road and gravel from San Quirico d’ Orcia to our next destination of Castelnuovo Berardenga, a true under the radar Tuscan village located at the southern end of the Chianti region.
-
After breakfast we’ll saddle up for a loop ride on some of the finest Cypress-lined gravel roads Tuscany has to offer. We return back to our lovely and authentic Agritourismo for another night. Dinner in the village center.
-
Again we pack our luggage for transport. We will point to point ride again on a mix of tarmac and gravel to Radda in Chianti, one of the loveliest villages in the region.
-
It’s a guides choice loop ride today. Most likely we will stay in the Chianti region and ride on the famous L’Eroica gravel roads that wind thoug the area.
-
Our final day we’ll wind our way through the hills en route back to Siena where we’ll finish in the historic Piazza del Campo where the world famous horse race Palio di Siena is held twice yearly.
-
Depart
accommodations
Palazzo Del Capitano
The atmosphere of a nobler Mansion of the fifteenth century blend with the warm welcome made of a little details and touches that change your holiday in an unforgettable experience.
A meticulous restoration has transformed the ancient building of XIV century in an elegant and charming 4 stars hotel joining tradition with modern comforts.
SERVICES: Reception and concierge, Air conditioning, Minibar, Free wifi, Comfort matress, Large flat screen Tv, Online magazines, Rooms with crystal showers box, Large crystal shower box, Romantic suites with crystal showers and whirpool tube and fireplace, Erbario Toscano Bathroom courtesy line, Telephone, Safe, Umbrellas, 1000mq Garden, Outdoor Pool, Relax area, Private Spa and Beauty centre Yon-ka, Video monitored parking with limited places (for a fee)
BREAKFAST ROOM: at the Trattoria Toscana “Al Vecchio Forno”, 50 meters from the Hotel
Borgo Scopeto
Hidden in the Tuscan hills of Chianti Classico, an enchanting driveway of cypresses leads to a precious gem of ancient origins. An enchanted oasis enclosed in a medieval hamlet that stands out in a breathtaking panorama of lush vineyards and olive groves, with its imposing tower that silently observes the city of Siena.