The best of Umbria and Tuscany

6 stages

From Assisi to Siena

8 days | 7 nights

from 1250€ per person

Cycle through Umbria and Tuscany: A journey of vineyards, art, and UNESCO heritage

Explore the beauty of Umbria and Tuscany, Italy’s most famous wine regions, on a cycling tour that combines stunning landscapes, rich history, and authentic flavors. This unforgettable journey takes you through some of central Italy’s most iconic destinations, offering unique experiences at every stop.

Start your adventure in historic Assisi
Your journey begins in Assisi, a medieval hilltop town and UNESCO World Heritage site. Discover some of the most remarkable frescoes of the early Renaissance and immerse yourself in the culture and spirituality of this extraordinary place.

Ride through the green hills of Umbria to Lake Trasimeno
From Assisi, cycle through sunlit vineyards and ancient olive groves to the sparkling waters of Lake Trasimeno, a peaceful haven surrounded by nature.

Cross into Tuscany and Discover the renaissance splendor of Pienza
On the other side of the lake, Tuscany welcomes you with its renowned vineyards. Stop for a wine tasting and visit Pienza, another UNESCO World Heritage site, celebrated for its Renaissance masterpieces, charming cobblestone streets, and breathtaking views. Explore historic palaces, magnificent cathedrals, or simply relax with a refreshing spritz in the main square.

Experience the Val d’Orcia and finish in Siena
Continue through the iconic Val d’Orcia, Tuscany’s rolling hills and yet another UNESCO site, before arriving in Siena, your final destination. Indulge in local specialties like the sweet panforte, artisan pecorino cheese, and world-class wines. Don’t miss Piazza del Campo, home to the traditional Palio horse race, and marvel at the city’s exceptional art and architecture from the 13th to 16th centuries.

Book your cycling tour through Umbria and Tuscany today!
Embark on a journey that blends culture, nature, and flavor. Cycle through vineyards, discover UNESCO heritage sites, and enjoy an unforgettable adventure in the heart of Italy!

TECHNICAL MANAGEMENT
Tour Operator

Info

Price includes:

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

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

Activity:
Self guided cycling tour on secondary asphalt roads.

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

Itinerary

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.