Essence Tuscany tour

Once in a lifetime cycling experience

Essence Tuscany tour join us on this total immersion into Tuscany land: back roads head into rolling hills and through the fortified medieval villages of an untouched Tuscany.

Goal of the Essence Tuscany bike tour is also to enjoy the genuine Tuscan food.

Fruity olive oil, pecorino sheep-milk cheese and classic best Tuscany wine: Brunello.

That has made Tuscany so famous, Chianti Classico and Nobile wine.

You will taste a selection of our favorite producers during our special events.
Cycling with the Tuscany’s guide the small group of adventure can enjoy a wonderful combination of nature, culture, cuisine and fun.



Day 1 – Pienza ‘the perfect town’

Meet at Chiusi-Chianciano train station.
Transfer to Pienza, the most perfect Renaissance town in the world.
Meet your guides, bike fitting session and get to know the rest of the group.
OPTIONAL depends on weather conditions and on time taken in the bike fitting Short ride to Bagno Vignoni.
The ancient village is located in the heart of Tuscany, in the Val d’Orcia Natural Park.
Thanks to the Via Francigena which was the main route followed by pilgrims in antiquity who went to Rome, these thermal waters were found and have been used since Roman times.
The heart of the village is the “Square of sources”, namely a rectangular tank of 16th-century origin, which contains the original source of water that comes from the underground aquifer of volcanic origins.
Welcome dinner in the wonderful La bandita townhouse Pienza, where you will taste special homemade pasta.

Day 2 – Montepulciano & Montichiello

Loop ride to Montepulciano and Monticchiello.
Level: Moderate to challenging
Start your day with a pleasant downhill, You’ll follow a route that winds through a scenic landscape checkered with vineyards, cypresses, and medieval village.
This is where “the English Patient” was filmed. Among the sites you’ll ride through there are the hilltop villages of Castelmuzio and Petroio.
Today’s ride will take you to Montepulciano, which is famous for the production of Vino Nobile di Montepulciano.
After a stroll about the medieval streets of this village, you can stop to visit one of the typical wine cellars in town, the oldest one is situated under the Ricci Palace.
Back to Pienza through Monticchiello, another hilltop village!
Total Distance 55 km/ 34 miles

Day 3 – Montalcino Brunello land

Loop ride Montalcino
Today we’ll start out on a long descent into the rolling green pastures of the Val d’Orcia.
You are now at Parco Naturale e Artistico della Val d’Orcia, an Unesco site. Imagine cycling up and down in a scene from painting.
Along the way face the hearty uphill to Castiglione d’Orcia, with the imposing Rocca A Tentennano.
After a rest, enjoy a long downhill to Sant’Antimo Abbey.
On your way to the Etruscan village and wine town of Montalcino you’ll pedal through magnificent vineyards.
Today it is even more famous thanks to the production of one of Italy’s premier fine red wines, Brunello di Montalcino.
Back to Pienza via San Quirico d’Orcia: stop in the village at Horti Leonini Garden, the top attraction of town.
Special event: Wine Tasting at Ciacci Piccolomini
Free dinner in town
Total Distance: 68 km/42,5 miles

Day 4 – Le crete & Castello di Gargonza

Le crete, Castelmuzio, Trequanda, Lucignano.
Your detailed directions will take you through typical postcard scenery of Tuscany, Italy’s most photographed region for good reasons. Following a picturesque road, you’ll ride by Castelmuzio, Trequanda.
Afterwards, you’ll travel through the fascinating area called Le Crete Senesi.
Tuscany’s answer to the Badlands with strange rock formations and lone farmhouses flanked by twin cypress trees.
Here the verdant hills give way to little domes of clay and Tuscany reveals another face of its identity, an unusual, almost lunar landscape of chalk cliffs and gullies soaked in a primeval atmosphere.
Cycle in the valley for a while and reach Lucignano, a small village that represents one of the more extraordinary examples of medieval urban planning for its system of elliptic rings arrived intact over the centuries.
Destination is a real castle restored – its magical!
Dinner at your Castello di Gargonza
Total Distance: 57 km/35 miles

Day 5 – Chianti wine & Abbeys

Castelnuovo Berardenga, Castello di Brolio, Pedaling north, we’ll whisk past a pair of typical southern Tuscany towns and make a stop at Castelnuovo Berardenga, a medieval town that marks the gateway to Chianti country.
From here you will ride inside the vineyard of famous chianti classico wine passing through many little hamlet.
Not to be missed is Castello di Brolio, castle and winery, home of Barone Ricasoli and his world-renowned wine.
Enjoy the up and down and get to your country resort hotel.
Before dinner we will be treated a Chianti Classico wine tasting in Felsina winery
Dinner at resort.
Special event: Chianti Classico wine tasting at Felsina
Total Distance 50 km / 31 miles

Day 6 – Gaiole, Radda & Ama

Circular bike ride to heart of chianti.
Bike along quiet roads to the three villages that formed the Chianti Alliance centuries ago.
Visit Tuscany’s forgotten abbeys and hamlets then enjoy a winery tour and taste their supple reds, fresh honeys and rich olive oil.
We’ll stop for lunch in Gaiole, a lively town located along the river Massellone and home to the annual l’Eroica vintage (pre-1987 steel frame) bicycle race.
A few more miles bring us to Radda in Chianti and the way back on the so called via dei Castelli not to be missed the stop at Castello di Ama to visit the winery and the borgo.
Relax by the vanishing edge pool spilling into the countryside of endless vineyards
Farewell dinner at your resort.
Total Distance: 62 km/39 miles

Day 7 – Arrivederci

Enjoy the farewell breakafst and wander in Siena!

Price & Inclusions


Cost: € 2.650 per person in double occupancy

single room supplement € 490


Six nights in superior hotels with private bath and breakfast

Four dinners, one lunch & two wine tastings

Snacks and drinks along the way

All maps, trip notes and detailed route directions

All Shuttles and technical assistance

Van Support, all baggage transfers

Experienced english speaking guides

water bottle

Sales taxes

Not included

Airfare to Italy, train to Chiusi, transfer on Day 7, 5 lunches, 2 dinners, alcoholic/non-alcoholic beverages, gratuities, travel insurance, laundry expenses and items of a personal nature

Bike Rental tour

Hybrid bike € 180

Race bike € 210

E-Bike € 210



Guided Bike Tour



Rolling hills and some climbs

rarely flat

Best Time







Go Private

Custom groups any time




Castelnuovo Berardenga Chianti

2021 Availability

May 25th to 31st

July 13th to 19th

September 21st to 27th

October 19th to 25th


  • Full immersion in Orcia Valley.
  • Stay in Pienza the ideal renaissance Town.
  • Magical stay at a real medieval castle Gargonza.
  • Riding through scenic landscapes where “English Patient” and “Gladiator” were filmed.
  • A private tour of the cantina of Brunello in Montalcino, one of the older winery Costanti.
  • Enjoy Chianti resort with wine and food focus.

You may also like: RIDE AND COOK LIKE A TUSCAN

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