The best of Umbria and Tuscany

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6 stages
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From Assisi to Siena
Senza titolo-1
8 days | 7 nights
from 1150€ per person

Bike through the splendor of Umbria and Tuscany, Italy’s most famous wine regions. Your journey will begin in the town of Assisi, a UNESCO World Heritage Site. Perched high on top of a cliffside, this medieval town hosts some of the most important early Renaissance frescoes in the world.

Descend down into the verdant hills of Umbria past sun-kissed vineyards & ancient olive groves until you reach the sparkling waters of Lake Trasimeno. On the other side of the lake lies many of the most famous vineyards in Tuscany, where you can stop for a tasting, as well as the town of Pienza, another UNESCO World Heritage Site renowned for its Renaissance masterpieces & charming cobblestone streets. Enjoy exploring the many palaces & cathedrals, or a refreshing spritz in the main piazza. Then it’s onwards through the most famous hills of Tuscany (and yet another UNESCO World Heritage Site), Val d’Orcia. Your final destination is the town of Siena (your fourth UNESCO World Heritage Site!). Here you can taste the nutty-sweet “panforte” cake, artisan pecorino cheeses & the unbeatable wines. You can also see some of the most notable art & architecture from the 13-16th centuries & visit the piazza where the 400-year old tradition of the Palio horse race takes place.


Tour Operator

Logo Via del Sole Tour Operator


Price includes:
  • 7 nights (in 3* / 4* accomodations)
  • All the breakfasts (dinners on demand)
  • Luggage transfer
  • GPS files
  • Emergency number 24/7

Assisi, Bevagna, Lago Trasimeno, Montepulciano, Monticchiello, Pienza, Buonconvento, Abbazia di Monte Oliveto Maggiore.

Self guided cycling tour on secondary asphalt roads.

Suitable for:
Adults and families (childrens from 15 years old).


Day 1: Arrival in Assisi
You will be met at Santa Maria degli Angeli station and transferred to your hotel. Visit this beautiful town which is within 10 minutes walk from your hotel. The next morning you are given your informative kit: road books, maps, guide book and vouchers, You will also receive and try your bikes.

Day 2: Assisi Loop
Today the ride takes you to Spello a very nice and less truistic small town on the Subasio Slopes. You will be riding through olive groves with no major uphill except for the final climb back to Assisi. Night at the same Inn. On the return road you can visit Bevagna going through the most famous wine area of Umbria, the Montefalco Sagrantino DOCG.

Day 3: From Assisi to Solomeo
On the way to Trasimeno lake an intermediate stop to allows you to visit Deruta a famous ceramic makers’ place and Torgiano, Lungarotti wineries home town; You bike through soft hills and nice villages until you reach Borgo Mandoleto Solomeo the cashmere village. The road is continuously rolling up and down hill so it is quite a tiring day.

Day 4: From Solomeo to Cortona
Discover Montecolognola view point over the lake, Monte del Lago and San Feliciano fisherman villages; Take a boat to Isola Maggiore where old ladies weave their age old laces and where you can taste a delicious fish at Sauro’s. Then continue to Cortona where you spend the night.

Day 5: From Cortona to Montepulciano
Today you enter Tuscany through the wine country of Montepulciano; however, before getting there, a naturalistic tour of the small Chiusi and Montepulciano lakes. Once in Montepulciano, tour this beautiful renaissance town not forgetting a visit to the superb Cantine de Ricci with their vaulted cellars town; have a taste of the “Nobile di Montepulciano ” at Gattavecchi winery, smaller, but very friendly.

Day 6: From Montepulciano to Buonconvento
After a visit of the San Biagio church, head for Pienza, the beautiful Renaissance town, home to Pope Pius the II and on the way discover the incredible “Crete” landscape with the barren hills, crowned by rows of cypresses. Stop in Monticchiello, for a cappuccino (or a glass of wine) with a view.

Day 7: From Buonconvento to Siena
The road to Monte Oliveto Maggiore Monastery is climbing gently from Buonconvento. Stop and visit the abbey before continuing to Asciano, a small town in the heart of the Crete, and from there to Siena. It is a though day with plenty of ups and downs, but the landscape is superb and very rugged. Spend the night in Siena in a centrally located 3 stars hotel.

Day 8: End of our services
Free time in Siena to visit the town before your departure for your next destination.

Book now or request info

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