Welcome to our guided Strade Bianche tour, the ultimate gravel cycling experience in Tuscany. Ride the white gravel roads through the UNESCO-listed Val d'Orcia, Montalcino, Siena and Gaiole, the birthplace of L'Eroica.
Along the way you taste Tuscany's three great wines (Vino Nobile di Montepulciano, Brunello di Montalcino and Chianti Classico) and enjoy the food and culture of each area. You stay in a converted historic monastery, a Brunello wine relais, a villa in Siena and a castle in Gaiole: each one a special experience.
The tour is ideal on a carbon gravel bike or an e-bike, and there are plenty of activities for non-riding companions. Available from March to November, it is a luxurious adventure of wine, history and nature for all the senses.
Tours are guided in English by our Italian team. If you live in Japan, our Japan office helps you with planning, booking and questions on LINE before departure.
Guided Gravel Cycling in Tuscany | 7-Day Itinerary
Day 1: Pienza and Bagno Vignoni
Meet at 12:00 at Chiusi-Chianciano station (a stop on the main Florence-Rome line) and transfer by private vehicle to the Renaissance town of Pienza. Pienza is considered the purest example of Renaissance town planning in the world, the "ideal city", and its cobbled lanes are full of beautiful architecture.
Check in to a hotel in a converted 15th-century monastery in the town centre. At 15:00, bike fitting, meet your guides and the rest of the group. If there is time, take a short ride to Bagno Vignoni, a spa village dating back to Roman times.
Welcome dinner at La Bandita Townhouse.
Distance: 25 km (12 km paved + 13 km gravel) Level: easy to intermediate
Day 2: Montepulciano and Vino Nobile
A loop from Pienza. Ride past the cypress avenues made famous by "Gladiator" and "The English Patient" and feel timeless Tuscany. After an espresso stop, reach Montepulciano around midday, a jewel of a town known for its Renaissance architecture. After a light lunch, enjoy a Vino Nobile tasting at one of our favourite cantinas. In the afternoon, ride on to Monticchiello, a picture-perfect hill village.
Distance: 51 km (17 km paved + 34 km gravel) Level: intermediate
Day 3: Pieve a Salti and the land of Brunello
From Pienza to Montalcino along part of the legendary Eroica route, through Lucignano d'Asso and Pieve a Salti. Stop for an espresso at the little emporio in Lucignano. After lunch in Buonconvento, a challenging climb takes you through the wineries up to Montalcino, famous for Brunello.
Overnight at the Wine Relais Mastrojanni, with a dinner paired with the estate's own Rosso and Brunello.
Distance: 48 km (mixed paved and gravel) Level: intermediate
Day 4: Castiglion del Bosco and Siena
Today you ride the legendary Eroica route, passing Castiglion del Bosco (the largest Brunello estate, owned by the Ferragamo family) and visiting Bibbiano and Murlo. Lunch at Ville di Corsano. Paved roads take you into Siena for the finish, with dinner at Babazuf.
Distance: 58 km (32 km paved + 24 km gravel) Level: intermediate to advanced
Day 5: Gaiole, home of L'Eroica
After breakfast, head into the magical Chianti region. Ride through wheat fields and vineyards via Pieve a Bozzone, part of the Eroica route. Lunch in Radda in Chianti. In the afternoon, on to Gaiole and an overnight stay at the charming Castello di Spaltenna. Dinner on your own.
Distance: 46 km (12 km paved + 34 km gravel) Level: intermediate to advanced
Day 6: The Chianti hills and Castello di Brolio
A day exploring the villages of Chianti. Espresso at the agri-bar at Brolio Castle, a favourite with cyclists. After a wine tasting (Felsina) and the small village of San Gusmè, return to Gaiole. Farewell dinner at the castle.
Distance: 54 km (44 km paved + 10 km gravel) Level: intermediate to advanced
Day 7: Arrivederci
Farewell breakfast at Castello di Spaltenna. End of tour.
Hotels across Tuscany
Pienza | La Bandita Townhouse
In Pienza's historic centre, La Bandita Townhouse is a luxury boutique hotel in a Renaissance palazzo where nuns lived for more than 500 years. It keeps its historic character while offering comfort and refinement.
Montalcino | Wine Relais Mastrojanni
At the Wine Relais Mastrojanni in Montalcino, enjoy quiet moments surrounded by vineyards, with superb views towards Monte Amiata. A luxurious stay in harmony with nature.
Siena | Villa STR
Villa STR in Siena is an elegant converted 19th-century villa, with beautiful classic Italian design, a quiet garden and an excellent location just a 10-minute walk from Piazza del Campo.
Chianti | Castello di Spaltenna
In the heart of Chianti Classico, Castello di Spaltenna offers the atmosphere of a historic castle and rooms overlooking the valley.
Every stay lets you enjoy Tuscany's landscapes and history with all your senses.
Tour price and what's included
Tour price
*The yen price shown is an estimate and varies with the exchange rate.
Payment is made in euros.
€3,400 per person (sharing a double room)
Single supplement: €850
Included
6 nights in luxury hotels (5-star, 4-star and 3-star superior) | 6 breakfasts | 2 wine tastings | 4 dinners | Route guidance, maps, elevation data and city maps | Sightseeing, restaurant and shopping tips | All luggage transfers | Cicloposse water bottle | Taxes
Not included
Bike rental (whole tour) | Gravel bike / e-bike: €260 | E-gravel: €350
Options
Airport transfers
Today's price in yen
Support from Japan
Our local staff speak Italian and English. Our Japan office helps you on LINE with questions, bookings and travel documents, in your time zone (not on site).
Even on your first cycling trip abroad, you can join with peace of mind.
What our Japan office offers
• LINE support, reply usually within 24 hours
• In emergencies, our local staff help in English
• Allergies and diets sent to restaurants in advance
• Travel documents also available in Japanese
Ride and taste Italy to the full, with support from Japan.
First cycling tour? Start here
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