Tuscany on a Vespa – 'La Dolce Vita'

Self Guided Tour - 7 Days / 8 Nights

Imagine cruising along winding country roads on a Vespa; picture-postcard vistas of rolling hillsides clad in a multitude of colours, fragrances and emotions. There are endless rows of vineyards bearing some of the world’s finest grapes; green forests of Holm oaks, beech trees, olive groves, parks, gardens, yellow broom, cornflowers, red poppies and the green of the meadows.
The sensory overload continues in every quaint, Italian, hilltop village along the way, where you’ll sip espresso at an outdoor café, sample Tuscan celebrated wines, or savour a long, leisurely meal bursting with fresh vegetables, homemade pasta, meat from the region's famed charcuterie, local cheese, prized truffles, river fish, lentils. All part of the region’s tradition and warm hospitality that has not succumbed to modernisation or haste. Unlike other tours, 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, waiting to be explored. The freedom and laugh-out-loud fun of discovering Tuscany by scooter will be an adventure to remember!

Your Journey

Day 1 Arrival in Poggibonsi.

You will be met at Poggibonsi train station and transferred to the Vespa office for an orientation and vespa fitting. Then a short ride to your villa accommodation, where you spend the night.

Day 2 Circuit ride to San Gimignano & Volterra (50 km)

Wander the cobbled lanes of San Gimignano, one of the most famous medieval towns in Tuscany with her landmark high towers and walls. Continue your Vespa ride along stunning roads to the ancient walled town of Volterra.

Day 3 Poggibonsi - Monteriggioni – Siena – Buonconvento – (65 km)

Ride a scenic route to Siena, full of ups and downs, but little traffic. Pass Monteriggioni, a nice hamlet very well preserved, before arriving Siena. Visit the famous Piazza del Campo, scene of the famous annual Palio horse race. Continue your ride to Buonconvento along the acient Cassia Roman way. Stay at an ‘agriturismo’ which has stunning views over Montalcino.

Day 4 Montalcino – Sant Antimo abbey – Pienza - Montepulciano (70 km)

An amazing day in the Val d’Orcia, a UNESCO Heritage site. Ride through the famous Brunello vineyards to San Antimo Abbey. Continue to the ancient Roman thermal baths at Bagno Vignoni then on to the Renaissance jewel, Pienza. End your day in the hilltop town of Montepulciano, well known for its’ characteristic vino 'Nobile',.

Day 5 Montepulciano – circuit ride or rest day with cooking class (50 km)

This is a day for meandering, enjoying the landscape, taking photos in the beautiful town of Montepulciano, with its' Renaissance palaces and wine caves featuring the characteristic “Nobile” wine. Relax at your villa or take a ride to Montefollonico. Along the route you can visit some cellars to taste the ‘Nobile Montepulciano’, one of the best red wines of Tuscany. Afternoon cooking class at your villa – have fun!

Day 6 Montepulciano – Siena (80km)

Ride through the red ‘Crete Senesi’, one of the most impressive landscapes in Tuscany. Perhaps have lunch at Trequanda or Asciano, where you can taste genuine recipes cooked with the truffles of Asciano. Tonight you stay in the centre of Siena, considered the best preserved medieval city in Italy.

Day 7 Siena - Chianti - Poggibonsi (75 km)

Welcome to Chianti, one of the most beautiful areas of Tuscany, set in hills, with vineyards, stunning villas and famous villages like Radda , Panzano and Castellina in Chianti. Stop at Volpaia castle to taste the Chianti ‘Black Rooster’ wine. Return to the villa where you started your Vespa tour for your last night.

Day 8 Return of Vespas

Arrangements end this morning. You are within a short taxi ride of Poggibonsi Station for onward travel to Rome or Florence. 


Quiet backroads, some steep cobbled terrain into villages. Participants must have had experience driving a scooter or Vespa of 125cc


Breakfast daily, 4 dinners.

Price 2023

Please note that pricing is per person in Euro

2023: Double / Twin Share €1489

Single supplement (travelling with others) € on request

Vespa rental €295

ESCORTED OPTION - for minimum 6 people with guide, supporting vehicle and extra inclusions. Double / Twin Share €2585 based on 6 participants


2023: Start any day April - October


The above is a short synopsis of this tour. This email address is being protected from spambots. You need JavaScript enabled to view it. for a more detailed itinerary and trip notes.


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A Walker’s World has been offering walking holidays in Europe and around the world since 1991.

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