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


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

contact us and book the tour

Share With Your Friends

Stay in Touch

Based on 96 reviews
Manuel König
Manuel König
I rented the Canyon Gravel bike for the Strade Bianche and felt I had made the optimal choice. The booking process was very easy, Luigi is extremely kind, knowledgeable and helpful, the bikes are beautiful, perfectly maintained and adjusted to your needs and the price is more than fair compared to competitors. 5/5 stars. I would come back any time.
Silvia Dagnoli
Silvia Dagnoli
Top! Professionalità e disponibilità al 100%. Ho preso una Canyon Gravel a noleggio, mi sono trovata molto bene.
Very friendly, speaks good english. The bikes themselves are great. The bikes are nog insured by default.
Matthew Ng
Matthew Ng
We had 5 excellent days of gravel riding (self guided Tuscany tour). The routes that Luigi provided us were a good mix of paved and gravel, and of course hills! The bikes (Canyon Grizl) were very nice and the luggage was always waiting for us at the next hotel. Luigi was accomodating, modifying the routes based on my requests. I would definitely recommend doing a trip with this company.
Robert Head
Robert Head
The route was wonderful, with amazing scenery and history at every turn. Our guides, Sarah and Gigi were the best. They are both very accomplished and personable riders, provided interesting history of Tuscany during the tour, and emphasied safe riding while keeping everyone within sight. They are also great dinner companions!
James Twidale
James Twidale
Luigi and BikeRiding Tuscany were an absolute pleasure to deal with. The bike was in incredible condition, delivered to my hotel and Luigi even arranged for a local mechanic to help with a small mechanical issue after my first ride. The experience from start to finish was brilliant. The communication friendly and quick. Simona was equally helpful on collection of the bicycle. I would love to join Luigi for a cycle tour as he seems very knowledgeable about the area and a good rider. I would recommend this company to anyone looking to explore Tuscany or Siena.
Mark Gatha
Mark Gatha
Exceptional self guided tour. I highly recommend for all levels (but especially for a road cyclist). This is the tour company to book with! Bikes - excellent high end bikes. I rode a Canyon Ultimate CF SL Ultegra - light and fast and we'll tuned with new tires. My wife road the e-mountain bike which she really enjoyed. Routes - beautiful. We did 50-60km a day. Rapolano de Terme, Pienza, Montalcino, Siena and Castellini in Chianti. Varied terrain, vineyards, great climbs and beautiful medieval towns. Extremely well thought out. All on quiet roads. Hotels - all 3 and 4 stars with loads of character. The ones with pools were our favourites. All of the hotels were able to let us check in very early (it was hot so we rode as early as we could manage). Hotels all came with breakfast. Really great. Service - Luigi was a gem. Easy to contact, quick to communicate (before we came and during the tour) and passionate about cycling. He gave us a lot of great recommendations to help maximize our tour. I cannot say enough positive things about this trip and Bike Riding Tuscany. This was truly memorable. Highly recommended.
Bruce Jenkins
Bruce Jenkins
I was on a trip around the world and stopped in Italy. A friend recommended BikeRidingTuscany to me for an unforgettable experience and it didn’t let down. They planned a custom 1 day gravel ride for me that took us from Rapolano Terme to Sienna and back. The pace was perfect and they were gracious with any requests for breaks or stops for water/food. I enjoyed myself so much that I extended my stay to do a run on the gravel amongst the beautiful sunflowers. If you’re adventurous, and seeking some safe fun riding, this is your team
greg luckos
greg luckos
Great rental service! Nothing is a problem for Luigi. All bikes are set up tubless. Thank you

BikeridingTuscany is

shimano original parts rivenditore ufficiale
Scroll to Top


L'invio della e-mail è avvenuto con successo.
Ti abbiamo inviato anche una e-mail di conferma, controlla la tua casella postale.
A volte può succedere che il messaggio sia classificato come spam.


The e-mail was sent successfully.
We have also sent you a confirmation email, please check your mailbox.
Sometimes it can happen that the message is classified as spam.