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There are more UNESCO World Heritage site in Tuscany than in Australia or South Africa

Italy Experiences

The Essence of Tuscany

Experience the Essence of Tuscany


The Essence of Tuscany Bike Tour is one of the best bike tours in Italy!

Pienza ~ Val d’Orcia ~ Montalcino ~ Chianti ~ Siena 7 day / 6 Night Guided Bike Tour

Join us on this total immersion into Tuscany: back roads head into rolling hills and through the fortified medieval villages of an untouched Toscana. The goal of this bike trip is to introduce you to Tuscany and genuine Tuscan cucina: fruity olive oil, pecorino sheep-milk cheese and classic best Tuscany wine: Brunello, that has made Tuscany so famous, Chianti Classico and Nobile. You will taste a selection of our favorite producers during our special events.

Day 1: Pienza “the perfect town”
We meet at the Chiusi-Chianciano train station at 12.00 this is a stop on all main Florence-Rome trainlines). Transfer to your hotel in Pienza, considered to be the most beautiful Renaissance town in the world. Check into your rooms at your hotel, which is located in a 15th century convent in the centre of town. 3.00 pm meet and greet with a bike-fitting session. This is followed by an optional but recommended short ride to Bagno Vignoni, an ancient village located in the Val D’Orcia, a UNESCO world heritage site described as “an exceptional reflection of the way the landscape was re-written in Renaissance times”. Renowned as part of a pilgrim route, the village is known for its thermal waters used since Roman times. Welcome dinner at the wonderful La Bandita townhouse in Pienza, where you can savour the homemade pasta!

Day 2: Montepulciano & Montichiello
Today’s bike ride is a loop ride of moderate to challenging level of difficult. Bike ride downhill, gentle rolling hills on a bike route that winds through a scenic landscape checkered with vineyards, cypresses, and medieval villages. TGhis is the location where ‘The English Patient’ was filmed. Among the areas you bike through today are the hilltop villages of Castelmuzio and Petroio. You also bike to Monetlpulciano, famous for its Vino Nobile di Montepulciano. Here we stroll through medieval streets and visit wine cellars, the oldest of whcih is located beneath the Ricci Palace. Retyrn to Pienza through Montichiello, another beautiful hilltop village! Distance 55km/ 34 miles

Day 3: Montalcino Brunello Countryside
Looped bike ride today to Montalcino. Your day starts with a long descent into the rolling green pastures of the Val d’Orcia. Every view looks like a Renaissance painting. Enroute we visit the beautiful Castiglione d’Orcia, with its imposing Rocca A Tentennano. Enjoy a rest stop and a lovely downhill ride to explore the Sant’Antimo Abbey. You may even hear the chants of the monks here. Continue through beautiful vineyards to the town of Montalcino. This fortified town is famous for its Brunello di Montalcino red wines. We recommend a wine tasting at Conte Pavone, an organic-biodynamic winery. Back to Pienza via San Quirico d’orcia with a stop at Horti Leoini Gardan, one of the towns top attractions. Dinner is provided at a local restaurant in the town. Distance 68km/ 42.5 miles

Day 4: Le crete & Castello di Gargonza
Today we visit Le crete, Castelmuzio, Trequanda, and Lucignano, biking through typical postcard scenery of Tuscany. Following a picturesque road, you’ll ride by Castelmuzio, Trequanda. Continuing on you through the fascinating area of Le Crete, Tuscany’s answer to the Badlands, with strange rock formations and lone farmhouses flanked by twin cypress trees. Here the rich green hills give way to little domes of clay to reveal an almost lunar landscape of chalk cliffs and gullies. Bike through the valley to Lucignano, a small village and an extraordinary example of medieval urban planning with its elliptic rings that have remained intact for centuries. Your destination this evening is a real castle restored – magical! Dinner at your Castello di GargonzaDistance 57 km/ 35 miles

Day 5: Chianti Country
Todays route visits Castelnuovo Berardenga and 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 little hamlets. Not-to-be-missed is Castello di Brolio, a castle and winery, home of Barone Ricasoli and his world-renowned wine an enjoy an amazing wine tour. After nice gentle downhill ride to reach Gaiole, a lively town located along the river Massellone. This village is home to the annual l’Eroica vintage (pre-1987 steel frame) bicycle race. Then an undulatig bike ride to Castello di Spaltenna in Gaiole. Dinner in the centre of town Distance 55 km/ 34 miles

Day 6: Castellina, Radda & Borgo di 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.. 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 il Pievano Michelin star restaurantDistance 62km/ 39 miles

Day 7: Arrivederci
Enjoy the farewell breakfast and wander in Siena!

What’s Included?

Trip Includes:
6 nights in superior hotels with private bath and breakfast
4 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

What’s not included?

Not included: Airfare to Italy, train to Chiusi, transfer on Day 7, 5 lunches, 2 dinners, beverages, gratuities, travel insurance, laundry expenses, gratuities, travel insurance, laundry expenses and items of a personal nature.

Dates and Pricing

Price: Euro 2,550 per person sharing (based on double accomodation)
single supplement Euro 590

Bike rental: 
Touring/hybrid bike: Euro 180
high-end road bike, E-bike or gravel bike: Euro 240

Helpful Notes

Dates 2022:

May 13 – 19
June 10 -16
September 23 – 29
October 7 – 13

Tour Accommodation:
6 nights in superior hotels