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The Best of Umbria and Tuscany

The Best of Umbria and Tuscany

From 850Euro per person

From Assisi to Siena
Bike through the splendor of Umbria & 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.

YOU CAN ALWAYS CUSTOMIZE YOUR TOUR (Departure Dates, Distance Km, Luggage transport, E-bikes, etc.) BY CONTACTING OUR TEAM



Assisi and Bevagna – the most famous wine area of Umbria.
Trasimeno Lake: Monte del Lago and San Feliciano fisherman village
Nobile di Montepulciano” wine tasting in a local winery
Pienza and Monticchiello
Buonconvento and the Abbey of Monte Oliveto Maggiore.


We transfer your luggage

Just leave it at the reception desk with your name tag & you will find it at your next accommodation.

We book your hotels

We will book double rooms with private bathrooms in 2- or 3-star hotels, boutique B&Bs, or agritourism estates. You will find the vouchers to each hotel in your welcome package.

We supply detailed route notes & maps

The route notes can be in English, Italian, French, or German. All maps have GPS tracking.

  • Destination
  • Departure
    Assisi to Siena
  • Included
    7 NIGHTS ( in 3 Star Accommodation )
    All breakfast ( dinners on demand )
    Emergency number 24/7
    Gps Files Available
    Luggage Transfer
    Road Book & Maps
  • Not Included
    11 NIGHTS ( in 3 Star Accommodation )
    2 Dinners
    5 Dinner package ( On Request )
    5 NIGHTS in 3-4 Stars Accommodation
    6 NIGHTS in 3* / 4* Accommodation
    8 NIGHTS in 3* / 4* Accommodation
    Pilgrim's "Credenziale" ( Stamp book )
    Wine Tasting in Umbria

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 boosk, maps, guide book and vouchers, You will also receive and try your bikes.

Day 2 – Assisi – Spello – Bevagna

Today the ride takes you to Spello a very nice and less turistic 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.

Distance: 50km


Day 3 – Assisi – La Corte del Poggio

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 la Corte del Poggio in Poggio delle Corti. The road is continuously rolling up and down hill so it is quite a tiring day.

Distance: 50km


Day 4 – Around Trasimeno Lake – Cortona

Discover Montecolognola view poin 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.

Distance: 50km


Day 5 – Cortona – 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.

Distance: 45km


Day 6 – Montepulciano – Buoncovento

After a visit of the San Biagio church, head for Pienza, the beautifull 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 Montichiello, for a cappuccino (or a glass of wine) with a view.

Distance: 45km


Day 7 – Buonconvento – 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.

Distance: 50km


Day 8 – End our service

Free time in Siena to visit the town before your departure for your next destination.

Accommodation Level


Day 1 - Assisi


Day 2 - Assisi Loop


Day 3 - Corte del Poggio


Day 4 - Cortona


Day 5 - Montepulciano


Day 6 - Buonconvento


Day 7 - Siena
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