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The Best of Umbria and Tuscany – UPGRADE

The Best of Umbria and Tuscany – UPGRADE

From 1200Euro per person

This tours comes from our best-seller “The Best Of – Assisi to Siena” with a different selection of lodging and experiences, that makes the level of the tour upgrade. All the places that you are going to visit are the best level of accommodations and wine and food experiences so that you will bring a piece of Tuscany in your heart forever! 

Check what we have picked for you, in the “Tour Plan” tab below.

Bike through the splendour 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.

  • Assisi and Bevagna
  • Trasimeno Lake: Monte del Lago and San Feliciano fisherman village
  • Pienza and Monticchiello
  • Buonconvento and the Abbey of Monte Oliveto Maggiore
  • Siena


  • The most famous wine area of Umbria.
  • Wine tasting in a historical wine cellar in Montepulciano
  • Cheese tasting in Pienza
  • Visit the museums of the Senes artists in Buoconvento
  • Taste Siena Food Tour ( optional )


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.   UPGRADE LODGING: Boutique Hotel in the city centre

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   UPGRADE LODGING: Boutique Hotel in the city centre UPGRADE EXPERIENCES: Wine tasting + lunch in a Sagrantino winery

Day 3 – Assisi – 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 Solomeo, a medieval village close to your next accommodation. The road is continuously rolling up and down hill so it is quite a tiring day. Distance: 50km UPGRADE LODGING: Superior room in your country house UPGRADE EXPERIENCES: Possible cooking class + dinner always included

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   UPGRADE LODGING: Spend the night in a 4-star hotel in the city centre UPGRADE EXPERIENCES: Visit the Etruscan Museum in town

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   UPGRADE LODGING: Charming B&B in town, suite or deluxe room UPGRADE EXPERIENCES: Wine tasting in a historic winery in the city centre

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   UPGRADE LODGING: Deluxe room in your country house UPGRADE EXPERIENCES: Special Tuscan dinner ( optional visit to a Brunello winery )

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     UPGRADE LODGING: Superior room in a 4* hotel in the city centre UPGRADE EXPERIENCES: Join our "Taste Siena" food tour, a different way to visit this town, discovering its history, food and traditions. ( Optional )

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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