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.
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
Highlights… so called 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
Cortona Etruscan town
Total distance: 52 km/32, 5 miles challenging ride
Montepulciano & Pienza
Total Distance: 55 km/34 miles
Val d'Orcia and Radicofani
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 65 km/40.5 miles
Montalcino & Brunello wine
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 46 km/ 28,5 miles
Monte Oliveto and Siena
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 km 60 km /37,5 miles
Hotel Villa Marsili - CortonaVilla 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 PienzaIl 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. www.relaisilchiostrodipienza.com
Hotel Giglio - MontalcinoA 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.
Chiostro Carmine - SienaIl Chiostro del Carmine has been meticulously restored from a XIV century Carmelite Monastry, place of history and holiness, remained intact in the centuries, with its delightful and quiet courtyard. It is situated a few hundred metres from the Siena Cathedral and from Piazza del Campo
Luxury upgrade in Pienza: Bandita TownhouseLa 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 RegioMore 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.
Cost: Euro 1350 per person in double occupancy
Single room Supplement euro 350
Solo Traveller Supplement Euro 450
Six nights in four & three-star superior hotels
Route notes, maps, elevation gain and city map
Sightseeing, restaurant and shopping suggestions
RidewithGPS App – offline navigation
All Baggage transfers
Delivery bike & equipment in Cortona
Pick-up of bikes and gear in Siena
Keepsake Cicloposse water bottle
Bike Rental per entire tour
Hybrid bike euro 180
Race bike, Gravel, E-Bike euro 210
City Tax each village charges a tax per day between euro 0,70 to euro 4,00