Under Tuscan Sun

Under Tuscan Sun

Under Tuscan Sun

Tuscany - Self Guided

Bike tour Cortona Tuscany, food and wine

Starting from Cortona on the border Umbria/Tuscany You will discover Montepulciano, Pienza, Montalcino and val d’Orcia, Le crete area through a landscape of sculpted curves designed over the centuries by wind, rain, and man.

 Wow Moments

  • Learn the rich history of Cortona, Land of the Tuscan Sun
  • Explore the medieval hilltop villages of Tuscany, each uniquely beautiful
  • Scenic cycling through the stunning landscape of the Val d’Orcia
  • The stark and alluring “lunar” terrain of the Crete Senesi region

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. Glorious ending in Siena 


Cortona Etruscan town

We’ll meet you at charming Villa Marsili (you can arrive by the train to Cortona/Camucia station)
After bike fitting and orientation you’re free to 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 dinner at one of our recommended restaurants.


Lake Trasimeno

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 Lake. 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: 50 km / 31 miles   |  +1042 m / -1038 m
difficult: challenge


Montepulciano & Pienza

Ride from Cortona to Pienza via Montepulciano, through vineyards.
This splendid little town – whose artistic and architectural heritage led it to be called the Pearl of the Cinquecento – has preserved its beauty intact.
Leave the hilltown taking soon a beautiful scenery back road leading you to Monticchiello: you are now at one door to Parco naturale e artistico della val d’Orcia.
It is an Unesco site with this main justification: “ The Val d’Orcia is an exceptional reflection of the way the landscape was re-written in Renaissance times to reflect the ideals of good governance and to create an aesthetically pleasing pictures.” Imagine cycling up and down in a scene from painting to get to the perfect Renaissance town Pienza, now famous also for the delicious sheep milk cheese: “pecorino”.

Total distance: 63,5 km / 39,5 miles  |   +1049 m / -1021 m


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, you’ll head back into the country, along some of those winding cypress-lined roads and stop in another medieval village Contignano. Have a light lunch to stoke your legs and back in the saddle take another scenery road back

Total distance 63,8 km / 39,8 miles  |  +1022 m / -1029 m


Montalcino & 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.

Total distance 44,4 km / 27,7 miles   |   +920 m / -876 m


Monte Oliveto and Siena

Bike ride from Montalcino to Siena via Monte oliveto Maggiore and Asciano
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 and admire frescos. Afterwards, you’ll travel through the fascinating area called Le Crete, Tuscany’s answer to the Badlands. Often described as Italy’s best preserved medieval city, Siena rivaled Florence for dominance in Tuscany during the 1300s. You’ll have time to take a leisurely stroll about this medieval art city in the afternoon and to visit Piazza del Campo square, Torre del Mangia and the famous Duomo. The main square is famous because here it is held twice a year the disputed “Palio” horse race, which opposes the 17 “contrade” of this fascinating city.

Total distance 56.7 km / 35,5 miles | +1035 m / -1217 m


Siena sightsee

Enjoy farewell breakfast – end bike tour: Arrivederci

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Tour start In Cortona
Tour end in Siena

under tuscan sun tour map



best period From March to end of October


TOTAL DISTANCE 278 km / 174 miles in 5 stages



Tour Reviews

18 October 2016

Giuliana, We want to thank you for a wonderful vacation! Everything that you planned and advised was perfect. The routes were gorgeous and challenging. That meant some of us worked hard, but we did it and now feel we can tackle any bike route. And for the stronger bikers, they talk of coming back to Tuscany to live so they can have that kind of biking all the time. The hotels were charming, friendly and well located. The restaurants were all delicious. Thanks again for a truly memorable vacation.

18 October 2016

Steve and I wanted to thank you for the wonderful bike tour through Tuscany. We had a great experience and want to come back many times! We loved the route you put together; it was such a great combination of fabulous riding, beautiful towns and so many fun experiences like wine tasting, gelato stops, etc. Thank you so much for your hospitality and caring about providing a quality experience. This was our first time to Italy and we know we will be returning!

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Price & Inclusions


Cost: Euro 1650 per person in double occupancy
Single room Supplement euro 550


Six nights in excellent four & three-star superior hotels
Six breakfasts
All Baggage transfers
RideWithGPS App: tracks, route notes, off-line navigation
Trip notes: Sightseeing & meals suggestions
Maps with elevation gain
Delivery bike at Cortona hotel & bike fitting
Pick-up of bikes and gear in Siena
Keepsake Cicloposse water bottle
Sales taxes


Not Included

Bike Rental per entire tour
Hybrid bike                                  euro 180
Race bike, Gravel, E-Bike         euro 240

City Tax   each village charges a tax per day between euro 0,70 to euro 3,00


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.www.villamarsili.net

Hotel Il Chiostro di Pienza

Il Chiostro di Pienza is housed in a 15th C convent and sits protected and quiet right in the center of this tiny town. It has been renovated but all the beamed ceilings frescoed walls and ancient tile floors have been preserved, nice garden overlooking val d’Orcia with pool

Hotel Giglio – Montalcino

A charming retreat in the heart of town, hotel Giglio, family-run, in a warm and quiet building, facing a gorgeous landscape, the best part is the view of the cliff-clinging houses of Montalcino to your left and the rumpled patchwork of green valleys stretching out below. Plus a great restaurant where enjoy gourmet tuscan dinners.

Villa di STR

Villa STR is a converted 19th-century villa that retains the charm and ambiance of its former origins as a private residence. The decoration in the recently renovated public areas bears the hallmarks of Italian classical design, with a quiet Garden for relaxing . Hotel is a 10-minute walk from Piazza del Campo

Luxury upgrade in Pienza: Bandita Townhouse

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 www.la-bandita.com

Luxury upgrade in Siena: Relais Campo Regio

More of a boutique guest house than traditional hotel, Campo Regio Relais’ 6 rooms are centrally positioned in the heart of Siena’s historic centre, allowing guests to easily reach the most important monuments of the city; the main square, Piazza del Campo, the Duomo, and the museums that house the masterpieces of Sienese art.

Luxury upgrade in Montalcino: Relais Mastrojanni

Relais Mastrojanni stands in Montalcino countryside,  the enchanting majesty of the Amiata valley offers visitors a unique panorama. Here, nature and the work of man merge in the harmony of vineyards alternating with holm-oak and oak woods, offering a unique view.

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