Hills & Wheels Luxury Tuscany Bike Tour | 6 Days
🇬🇧 English-speaking staff
Intermediate+
approx. 230 km
Climb approx. 4,200 m
approx. ¥484,000~
6 days
A boutique hotel in Pienza, a monastery hotel in Siena and a Chianti castle: ride from the Val d'Orcia to Chianti, staying in fine hotels
A self-guided tour to enjoy freely, without a guide 📅 Choose your own departure date.
A 6-day, 5-night bike tour from Pienza in the Val d'Orcia to Gaiole in Chianti, staying in carefully chosen luxury hotels every night.
Two nights in a boutique hotel in a 500-year-old palazzo in Pienza, with a loop through Brunello country. Then through the Crete Senesi to Siena, where you stay in a converted 14th-century monastery.
The last two nights are in a castle hotel in Gaiole, in the heart of Chianti Classico, riding among vineyards and wooded hills to Brolio, Castellina and Radda. Gaiole is also the home of L'Eroica, the vintage bike event.
From the Val d'Orcia to Chianti | 6-Day Itinerary
From Pienza in the Val d'Orcia via Montalcino and Siena to Gaiole in Chianti: a 6-day, 5-night luxury cycling itinerary.
Day 1 | Pienza
Welcome to the Val d'Orcia
Arrive by train at Chiusi-Chianciano (Rome–Florence line) and meet the Cicloposse team in Pienza for the bike fitting.
If you like, take a short ride to Bagno Vignoni, a spa village used since Roman times.
Day 2 | Montalcino
A loop through Brunello country
A long descent through the green hills of the UNESCO-listed Val d'Orcia, a hearty climb to Castiglione d'Orcia, then a long descent to the abbey of Sant'Antimo.
Through the vineyards to Montalcino, then back to Pienza via the Horti Leonini garden in San Quirico d'Orcia. A shorter option (46 km) is available.
Distance: 68 km | Elevation: +1,391 m / -1,396 m
Day 3 | Siena
Through the Crete Senesi
Postcard scenery through the Crete Senesi, Tuscany's "badlands".
Enter Siena by Porta San Marco, with the afternoon free for Piazza del Campo, the Torre del Mangia and the Duomo.
Distance: 56 km | Elevation: +961 m / -1,110 m
Day 4 | Gaiole in Chianti
The road of castles and the Eroica town
Via Castelnuovo Berardenga, the gateway to Chianti, onto a road of deep green hills and castles, stopping at Brolio, seat of the Ricasoli family since 1067.
Your destination is Gaiole, home of L'Eroica vintage bike event. Two nights here.
Distance: 45 km | Elevation: +831 m / -773 m
Day 5 | Castellina and Radda
A loop through the Chianti hills
Over hills of vineyards and forests to Badia a Coltibuono, an 11th-century abbey.
On to Castellina and its Via delle Volte, a walkway built into the walls, and back via Radda.
Distance: 57 km | Elevation: +1,066 m / -1,063 m
Day 6 | End of tour
A morning at the castle
Farewell breakfast at the castle. Optional short ride to San Sano and Ama.
Hotels in Pienza, Siena and Gaiole
On this tour you spend two nights in Pienza, one night in Siena and two nights in Gaiole in Chianti, all in 4- and 5-star luxury hotels.
Pienza | La Bandita Townhouse (2 nights)
A Renaissance palazzo in Pienza's historic centre, home to nuns for over 500 years, with the warmth of a local home and stylish comfort.
Siena | Certosa di Maggiano (1 night)
A 14th-century monastery about a mile from Siena's gates, its monks' cells turned into elegantly designed rooms.
Gaiole | Castello di Spaltenna (2 nights)
A castle hotel at the edge of Gaiole in the heart of Chianti Classico, with valley views, a beautiful pool and two restaurants.
Tour price and what's included
Tour price (tax included)
€2,750 per person (sharing a double room)
Single room supplement: €750
*The yen price at the top of the page is an estimate and varies with the exchange rate. Payment is made in euros.
Included
5 nights in luxury 4-star and 5-star hotels
5 breakfasts
All luggage transfers, including between hotels
RideWithGPS app (route data and offline navigation)
Trip notes with sightseeing and food tips
Route maps with elevation profiles
Bike delivery and bike fitting at your hotel in Pienza
Bike and equipment collection in Gaiole
Cicloposse water bottle
Taxes
Not included
Bike rental (extra cost)
City tourist tax (€0.70 to €3 per night, depending on the town)
Optional wine tasting
Bike rental prices
Hybrid bike: €190
Road bike, e-bike or gravel bike: €260
E-gravel bike: €350
*Prices cover the whole tour.
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
Fitness, bike choice, what to pack: everything first-timers ask about, in one place.
Have you checked the packing list?
Have you chosen your rental bike?
Questions about the tour? Just ask us!
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