Umbria & Tuscany on a Vespa

Self Guided 8 days / 7 nights

Guided 9 nights/ 10 days - If you have a small party we can provide the options of a guide, support vehicle, cooking classes, wine and olive oil tastings and dinners.

Imagine cruising along winding country roads on your Vespa; picture-postcard vistas greeting you around every corner of the Umbrian rolling hillsides. Experience the multitude of colours, fragrances and emotions. Enjoy endless rows of vineyards bearing some of the world's finest grapes. Picture green forests of Holm oaks, beech trees, olive groves, parks, gardens, yellow broom, cornflowers, red poppies and the green of the meadows.

Your journey becomes magical because the sense of discovery, suggestion, interest and curiosity never ends: suddenly you come across a medieval village, a little parish church, a city gate, a castle. At every stop, you'll be surrounded by the warmth and hospitality of the Italian people.

The sensory overload continues in every quaint Italian village along the way, where you'll sip espresso at an outdoor café, sample Umbrian prized wines, or savour a long, leisurely meal bursting with fresh vegetables, homemade pasta , meat from the regions famed charcuterie, local cheese, prized truffles, river fish, lentils all part of the country’s tradition and have not been affected by modernisation or haste.
Unlike on any other tour, you'll do it all in the Italian fashion: riding a Vespa scooter, with the sun on your face and the open road before you, just waiting to be explored. The freedom, camaraderie and sheer, laugh-out-loud fun of discovering Umbria by scooter will be an adventure you'll remember the rest of your life.

Your Journey - Guided

Day 1: Perugia

Arrive in Perugia late morning. Perugia, the capital of the Umbria region, lies at the heart of Italy in a peaceful and beautiful landscape. This is simply an arrival day so you may arrive in Perugia at any time. Note that hotel rooms are generally only available after midday. Late afternoon we meet Giuliana, Beppe, Paolo (our tour leaders) and our fellow travelling companions at a Welcome Meeting (usually at 4pm, but you will be advised as to the exact time and place in a notice, located near the reception at our hotel) where you will give us a briefing on what lies ahead on our tour. Dinner not included.

Day 2: Perugia – Cortona

After breakfast transfer to the Vespa rental location to receive your bikes and tour information. Ride to Cortona, the town made famous by Frances Mayes’ book, “Under the Tuscan Sun” passing Lake Trasimeno on our way. Lake Trasimeno (Italy’s fourth largest lake covering some 126 km²) is classified as a Regional Park, and its circular waters, surrounded by gentle hills are covered in olives and vines. Overnight: Villa Aurea

Day 3: Cortona – Montepulciano

This morning we ride a short distance (40km) to Montepulciano, in order to give you the time to get acquainted with your Vespa and with Italian roads. Montepulciano, a small yet magnificent Renaissance town. Inside the walls, the streets are crammed with Renaissance-style palazzi and churches. From here, you have your first view of the “Nobile” vineyards and cypress crested hills. It is the home of one of Italy’s much praised wines – Vino Nobile di Montepulciano.

Day 4 Montepulciano – /Pienza/ Monticchiello – Montepulciano

Visit Montepulciano before heading to Monticchiello, a tiny hamlet with cobbled alleys and geranium window-boxed gardens. Have lunch on the terrace of a small café that commands one of the most beautiful views of the whole trip. After lunch we travel to Pienza where you will taste pecorino cheese. Pienza is a wonderfully preserved tiny Renaissance ‘city’ with a fine Duomo, museum and Palazzo. Return to Montepulciano for a wine tasting at Cantine Redi.

Day 5: Montepulciano - San Casciano Bagni

The route to San Casciano Bagni is an amazing sequence of grand sceneries; visit Bagno Vignoni, the Roman ancient thermal baths and Radicofani, dominated by its imposing “Rocca”.

An afternoon cooking course at a charming country estate. After the cooking class have a relax in the hot pool at Fonteverde Natural Spa Resort then head back to your overnight accommodation and the dinner you prepared earlier in the day.

Day 6: San Casciano Bagni – Orvieto

Today you return to Umbria. Orvieto is a small jewel perched on a ‘tufo’ cliff. Tufo is a soft golden stone. Some of the ancient caves have now been turned into wine cellars. Visit a famous wine cellar and enjoy supper there.

Day 7: Orvieto – Montefalco

Today you travel past the lovely Lake Corbara to Todi. Continue towards Montefalco.

Day 8: Montefalco – Bevagna – Assisi

Today follow small country roads, winding among luscious vineyards. Stop for lunch and wine tasting at Dionigi winery and visit the charming town of Spello. Spello’s medieval town centre boasts numerous Roman remains, such as the theatre, amphitheatre, baths and the Arch of Augustus, an ancient gate leading into this former acropolis. Late afternoon cooking class and dinner at Alfonsas house (15kms from Assisi) . Overnight in Assisi.

Day 9: Assisi - Villa Il Poggiolo

Today you return your Vespas at Villa il Poggiolo, a charming 19th century villa where you will spend the night. Join Cristina at the Saturday market (dependent on market days) to buy food for dinner and in the late afternoon prepare bruschetta and appetizers while in the relaxing environment of her home.

Day 10: Tour concludes

Your tour concludes today with a transfer to the Perugia railway station or airport.




Breakfast daily; 2 dinners on the independent option; 7 dinners on the guided trip plus wine tastings and cooking classes.

Trip Notes / Dates / Prices (Guided)

If you have a small party we can provide the options of a guide, support vehicle, cooking classes, wine and olive oil tastings and dinners.

Contact Us

  • 306 Lake Road, Takapuna
    Auckland 0622, New Zealand
  • P: (0064) 09 486 7473
    F: (0064) 09 484 0091

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Cycling Europe Offers Cycling Holidays in Europe and around the world.

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