Once in a Lifetime bike tour Tuscany

We’we captured the essence of glorious Tuscany best scenery roads to cycle: we start the tour staying at beautiful Villa Marsili, in Cortona.  Let you discover Montepulciano, Pienza & val d’orcia; le crete area through a landscape of sculpted curves designed over the centuries by wind, rain, and man.
The mystique of this land lies not only in its landscape, but also in its nature, its vineyards and its history: oak woods, olive groves and vineyards watch over enchanting hillsides, medieval villages and historical monuments. Each day you rise, enjoy good coffee espresso or Cappuccino, cycle for five or six hours in the fresh air, and spend the night in a warm, welcoming inn.



Nice to meet you! Transfer from Chiusi station to the charming Villa Marsili. Bike fitting session. Explore this delightful hill town, made famous by Frances Mayes in her bestselling novel Under the Tuscan Sun, Stroll the winding narrow - and steep! - medieval streets, then enjoy a fabulous .
Welcome dinner at Le Loggette in main square.

Lake Trasimeno and Valle di Pierle

Ride to Valle di Pierle and his splendid castle “Rocca”. The history of Val di Pierle is closely linked to the history of the splendid castle (la Rocca) that dominates the valley. The castle was built prior to the 10th century and belonged to the marquises of Monte Santa Maria Tiberina. Another climbs and reach the top of hill Cima di Tuoro from where you will be able to enjoy a stunning view of the Lake and its islands From the top enjoy the nice downhill to Tuoro sul Trasimeno. You are in Umbria region now, in Tuoro you can stop in the village at the beach. On the saddle again and back to Cortona on gentle terrain but remember last climb!!
Total Distance 52 km/32, 5 miles challenging ride

Montepulciano & Pienza

Ride from Cortona to Montepulciano, This splendid little town – whose artistic and architectural heritage led it to be called the Pearl of the Cinquecento – has preserved its beauty intact. Going up the steep streets of its outlying districts you will discover beautiful palazzos and churches. Back in the saddle and after 15 km let’s stop in the village of Monticchiello, the quintessential Tuscan hill town. Bold cypress trees line our route to the orcia valley where you bike through the fields that inspired Renaissance painters. Il Chiostro di Pienza is housed in a 15th-century convent in a quiet, secluded location right in the center of Pienza - itself is a rare masterpiece: entirely rebuilt between 1459 and 1462, it was the brainstorm of Pope Pius II. Gourmet Dinner at your hotel La Bandita Townhouse
Total distance: 60 km/37,5 miles

Val d'Orcia and Radicofani

Circular bike ride into Orcia valley: is a completely country ride and for the first 15 km you will ride downhill and very easy gentle rolling hills. Then the gentle climb to reach Radicofani, a medieval and enchanting village with a 1200 dating Rocca. After a stroll around the stately old town, we'll head back into the country, along some of those winding cypress-lined roads. On the way back we will have a “pecorino” sheep milk cheese tasting at Pianporcino organic farm. Free dinner in town.
Total distance 66 km / 41 miles

Montalcino and Brunello wine

First pause in fairy-tale Bagno Vignoni, a miniature spa that is among the most unique towns in Europe, then push on to the monastery of Sant'Antimo, where you might catch one of several vesper services performed each day by the monks.
The famed wine town of Montalcino is your highlight: visit the fortress to see a breathtaking view of the entire valley you've just biked. Back in the saddle and enjoy the long downhill and flat part to reach the winery. Lunch at the cellar and brunello wine tasting. Back to Pienza by bike or bay van. Dinner at Dopolavoro at la Foce
Total Distance 68 km/42,5 miles

Le crete & Chianti wine region door

Enjoy the donwhill from Pienza, first stop Giovanni d’asso The ancient borgo of San Giovanni d’Asso, is famous worldwide for its valuable white truffle, is rich with farms, hamlets and castles, which are reminiscent of the colors of the paintings of the Renaissance. On the way you'll coast along the forested crest of a ridge, home to the famed Monte Oliveto Maggiore monastery. Stop here to visit the beautiful buildings. Afterwards, you'll travel through the fascinating area called Le Crete, Tuscany's answer to the Badlands. Your destination is a charming luxury castle chianti wine region. Farewell dinner at il Pievano Michelin star restaurant
Total distance 66 km / 41 miles

Siena Sightsee

Arrivederci - end of bike tour - explore Siena on your own before reach train station for your next destination in Italy
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La Bandita Townhouse - Pienza
La Bandita Townhouse is a luxury boutique hotel tucked inside the historic center of Pienza. The building is a rambling Renaissance-era palazzo where nuns have lived for over 500 years. the property itself blends in completely with the Renaissance character, is a comfortable, and stylish place.
Hotel Villa Marsili - Cortona
Villa Marsili is situated inside the town walls in Cortona and dates back as far as the XIV Century where the site actually housed the very old church named Madonna degli Alemanni, as well as an Oratory below. Later in the 1700s, the site held the villa that now has become the beautiful Hotel.
Castello di Spaltenna - Gaiole
A sophisticated manor, Castello di Spaltenna offers an exclusive atmosphere amidst a unique landscape. Located in the heart of the Chianti Classico wine region, the manor’s luxurious guestrooms offer any possible comfort along with wonderful views over the valley. From the grassy terraces, guests can enjoy the calm of the countryside and beauty of the surrounding landscape

Bella Tuscany

Price & Inclusions

Cost: Euro 2950 per person in double occupancy
single room supplement euro 550

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 transfer
Services experienced guide
Cicloposse water bottle
Sales taxes

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

Bike Rental for entire tour
Hybrid bike   euro 180
Race bike       euro 210
E-Bike            euro 210


Tour Reviews

15 Ottobre 2016

Just a little note to thank you once again for a fantastic cycle tour. Everything was organised perfectly and the hotels were just too divine for words. You guys always put such a great effort into making sure that everyone is happy and caring for everybody’s needs. YOU ARE THE BEST!!!!!

15 Ottobre 2016

Trisha and I wanted to thank you for putting together such a great trip for us. We had a great time; and now shortly before our departure back to the states, we’re already missing the wonderful towns of Tuscany. Although sometimes a bit arduous, the riding was fantastic. We have a lot of wonderful memories to share; and we will be back. Thanks again.

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