Tuscan Wine Country Bike Tour | 7 Days
🇬🇧 English-speaking staff
Intermediate+
approx. 285 km
Climb approx. 5,100 m
approx. ¥308,000~
7 days
Vino Nobile in Montepulciano, Brunello in Montalcino and Chianti Classico: Tuscany's three wine regions, one after the other, by bike
A self-guided tour to enjoy freely, without a guide 📅 Choose your own departure date.
A 7-day, 6-night bike tour from Pienza in the Val d'Orcia to the hills of Chianti, through the home of Tuscany's three great red wines: Vino Nobile di Montepulciano, Brunello di Montalcino and Chianti Classico.
Two nights in Pienza and a ride to Renaissance Montepulciano. Then on to Montalcino via the spa village of Bagno Vignoni and the abbey of Sant'Antimo, and to Siena through Monte Oliveto Maggiore and the Crete Senesi.
The last two nights are in Castellina in Chianti. Ride among the vineyards to Brolio Castle, Greve and Panzano, and taste local wine and olive oil at the wineries.
Through Tuscany's Three Great Wine Regions | 7-Day Itinerary
From Pienza in the Val d'Orcia to Montepulciano, home of Vino Nobile, to Montalcino, home of Brunello, through medieval Siena and on to the Chianti hills: a 7-day, 6-night itinerary through Tuscany's three great wine regions.
Day 1 | Pienza
The Renaissance "ideal town"
Arrive in Pienza for a welcome and bike fitting. Pienza is a rare example of Renaissance town planning, and its cobbled lanes are a joy to wander.
If you like, take a test ride to San Quirico d'Orcia.
Optional ride: 20 km
Day 2 | Montepulciano
To the town of Vino Nobile
A loop from Pienza, past the convent where parts of The English Patient were filmed and the little hamlet of Castelmuzio.
By lunchtime you reach Montepulciano, the jewel of southern Tuscany, full of Renaissance palaces. Return to Pienza via Monticchiello, the quintessential Tuscan hill town.
Distance: 53.5 km | Elevation: +1,068 m / -1,070 m
Day 3 | Montalcino
Into Brunello country
Stop at the spa village of Bagno Vignoni and have lunch in Castiglione d'Orcia. At the abbey of Sant'Antimo you may hear the monks' vespers.
Just before Montalcino, an optional Brunello experience at a wine estate: cellar visit, tasting of Brunello and Rosso di Montalcino, and lunch.
In Montalcino, enjoy the view from the fortress and a glass at a local enoteca.
Distance: 44.4 km | Elevation: +920 m / -876 m
Day 4 | Siena
Abbeys and the Crete Senesi
Along a scenic ridge road to the abbey of Monte Oliveto Maggiore, a 13th-century Benedictine monastery famous for its frescoed cloister.
Then the Crete Senesi, Tuscany's "badlands", where green hills give way to clay domes and an almost lunar landscape.
Distance: 56.7 km | Elevation: +1,035 m / -1,217 m
Day 5 | Castellina in Chianti
North along the Chiantigiana
From Siena along the Chiantigiana road, via Castelnuovo Berardenga, the gateway to Chianti, and through the Chianti Classico vineyards.
Don't miss Brolio Castle and its winery. Light lunch in Radda, then the last 10 km of gentle hills to Castellina, your base for two nights.
Distance: 55.6 km | Elevation: +1,019 m / -787 m
Day 6 | Greve and Panzano
Florentine Chianti
A loop on quiet roads to the villages of the old Chianti League, with forgotten abbeys, small hamlets and a winery tour with red wine, honey and olive oil.
Stop in Greve with its triangular porticoed piazza, and return via the walled village of Panzano. Relax by the pool overlooking the vineyards.
Distance: 55 km | Elevation: +1,019 m / -1,019 m
Day 7 | End of tour
On to Florence
The tour ends after breakfast. Trains and buses connect to Florence.
On request, an extra stage to San Gimignano via Monteriggioni (58 km).
Hotels in Pienza, Montalcino, Siena and Chianti
On this tour you spend two nights in Pienza, one night each in Montalcino and Siena, and two nights in Castellina in Chianti.
Pienza | Il Chiostro (2 nights)
A converted 15th-century monastery on Pienza's main street, with a beautiful cloister and a garden pool overlooking the Val d'Orcia. Right in the centre, yet very quiet.
Montalcino | Vecchia Oliviera (1 night)
Just inside the historic centre next to an old town gate, easy to reach by bike. Breakfast on a panoramic terrace, a small outdoor pool, and restaurants and wine bars a short walk away.
Siena | Villa STR (1 night)
A converted 19th-century villa about 10 minutes' walk from Piazza del Campo. Bikes are stored in the garage, so you can explore Siena on foot, then relax in the quiet garden.
Castellina in Chianti | Palazzo Squarcialupi or Salivolpi (2 nights)
Palazzo Squarcialupi is a 4-star hotel on the village's main street, part of the old town walls, with a garden and pool overlooking the Chianti countryside. Salivolpi is a traditional country house just outside the village, surrounded by vineyards, olive groves and cypresses, with a pool.
Luxury version (price on request)
On request, upgraded hotels: La Bandita Townhouse in Pienza, Palazzo Saloni in Montalcino and Certosa di Maggiano in Siena.
Tour price and what's included
Tour price (tax included)
€1,750 per person (sharing a double room)
Single room supplement: €650
*The yen price at the top of the page is an estimate and varies with the exchange rate. Payment is made in euros.
Included
6 nights in hotels (4-star and 3-star superior)
6 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 Castellina
Cicloposse water bottle
Taxes
Not included
Bike rental (extra cost)
City tourist tax (€1 to €3 per night, depending on the town)
Optional winery tasting and lunch
Bike rental prices
Hybrid bike: €200
Road bike, e-bike or gravel bike: €250
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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