Total tour distance: 178 miles
Daily tour distance: 30 miles
Difficulty: 70 / 100
Tuscany is an iconic name, symbolizing the good life - a vacation to enjoy all that is good: food, sun, lifestyle, wine, amusement, and relaxation. The culture of the region adds charm, and you can indulge yourself in this opulent way because you will cycle the famous undulating countryside. This Tuscany cycling tour starts in Montepulciano and goes to Pienza, where along the way you will visit the villages that have made Tuscany famous. You can enjoy very charming 3/4 star accommodations and devour your choice of divine Mediterranean cuisine. The hilly terrain makes this tour somewhat challenging!
Day 1 l Arrival Day in Montepulciano
Arrival Day - we will meet you in Montepulciano & vino nobile. Arrive by train at Chiusi and either bus or taxi to hotel.
This splendid little town - whose artistic and architectural heritage led it to be called thePearl of the Cinquecento - has preserved its beauty intact. Going up the steep streets of its outlying districts you will discover beautiful palazzos and churches imbued with the unparalleled art of foremost Renaissance architects. Orientation meeting late afternoon and then dinner on your own.
Day 2 | Loop ride to Pienza spinning across Val d'Orcia. Distance 55 km
From Montepulciano Beautiful loop to start you tour: leave Montepulciano taking soon a secondary road through Vino Nobile vineyards, enjoy the beautiful scenery of this back road leading you to Monticchiello for your first stop. You are now at Parco Naturale e Artistico Della Val d’Orcia, a Unesco site with this main description: “ 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 mill cheese: “pecorino”. Have a light lunch to stoke your legs and back in the saddle take another scenery road inside olive grove via little hamlet Castelmuzio and Petroio and get back to your hotel near to central square. Lodging hotel Duomo, Breakfast included.
Day 3 | Cortona and the Tuscan Sun. Ride from Montepulciano to Cortona via Val di Chiana. Distance: 45km.
From Montepulciano start a pleasant five-mile descent through the vineyards, where the only sound is the wind in our hair. Ride through some of the most beautiful vineyards in Tuscany. Then enjoy a long stretch on completely flat Val Di Chiana…through farmland, relaxed and glowing. It's time to set off on a long, slow climb towards Cortona, the delightful hill town made famous by Frances Mayes in her bestselling novel Under the Tuscan Sun. Reach your nice hotel in a corner of the main square and explore the magical town. Lodging hotel San Michele, Breakfast included.
Day 4 | Loop ride to Lake Trasimeno and Valle di Pierle. Distance 52 km
Ride to Valle di Pierle and its 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 Marquise of Monte Santa Maria Tiberina. Another climb and you'll reach the top of hill Cima di Tuoro from where you will be able to enjoy a stunning view of Lake Trasimeno and its islands. From there enjoy the nice downhill to Tuoro sul Trasimeno, crossing briefly to Umbria. In Tuoro you can stop in the village at the beach. On the saddle again and back to Cortona on gentle terrain but remember that last climb to Cortona! Lodging at Hotel San Michele in Cortona, breakfast included.
Day 5 | Montisi & le Crete area - Bike from Cortona to San Giovanni via Trequanda. Distance 55 km.
Enjoy the 3 miles downhill and cycle on flat terrain in the valley for another 15 miles. Afterwards, the terrain will be rolling while you ride to the medieval village of Trequanda, one of the most unspoilt areas of the province of Siena. It was developed around a 13th century castle of which a cylindrical tower still remains today. Stop at s the ancient borgo of Montisi, a natural bridge between the "Crete Senesi" and the Val d’Orcia. And now enjoy the rest of your day going downhill to get to San giovanni d’Asso, famous worldwide for valuable white truffle. The area is rich with farms, hamlets and castles, which are reminiscent of the colors of the paintings of the Renaissance. Your accommodation for the next 2 nights is the restored castle of the town: Lodging Locanda del Castello, breakfast included.
Day 6 | Montalcino & Brunello - ride from San Giovanni to Montalcino via Monte Oliveto. Distance 50 km
Today you'll travel through the fascinating area called Le Crete, Tuscany's answer to the Badlands. On the way you'll coast along the forested crest of a ridge, home to the famed Monte Oliveto Maggiore monastery. Stop there to visit the beautiful buildings and frescoes in the cloister. From the monastery enjoy a long gentle downhill to Buonconvento, so you're warmed up for the uphill to Montalcino. The famed wine town of Montalcino is the highlight of today's ride: Visit the fortress to enjoy a breathtaking view of the entire valley you've just biked. Montalcino is a fortified town which was used as a shelter by Siena nobles during the 16th Century, the origin is Etruscan, but today it is even more famous thanks to the production of one of Italy's premier fine red wines, Brunello di Montalcino. Take your time… the way back is downhill and flat road, so rare in this area! Lodging at Locanda del Castello, breakfast included.
Day 7 l Departure Day - Optional short loop ride to Asciano - Distance 30km.
Departure after breakfast, at your leisure. From San Giovanni d'Asso, you can take a bus to Asciano or Bun convento, then a train to where you need to be in Italy. If you have time in the morning, you can also enjoy one last bike ride with a short loop to Asciano, about 30km.
- Deluxe lodging 3 and 4 stars - double room with private bath
- Buffet breakfast daily
- All luggage transfers from hotel to hotel
- Local emergency support throughout your tour during daylight riding hours
- Arrival orientation and bike set up
- Route maps, route cue sheets with suggestions for visitation and site information
- All pre and post travel planning services
- A package of pre-travel documents sent electronically to help you prepare for your trip.
Stay in deluxe 3 & 4-star hotels in convenient locations. All lodging includes private bathroom and a variety of other amenities. Hotels included:
- Albergo Il Marzocco
- Hotel San Luca
- La Locanda di Montisi
- Hotel Il Chiostro del Carmine
- Hotel Il Giglio
- Relais il Chiostro.
Upgrades available – please inquire
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