Australia (+61) 400 191 511

Italy (+39) 331 4253965


Vespa Tour

What better way to experience Tuscany than on a Vespa! Drive through the hills of Tuscany to iconic locations taking in the true beauty of this region. Travel as a local, not a tourist as you indulge in regional food, wine and all things Tuscan.


  • Tuscan Villa Accommodation (one location)
  • Experience the Tuscan Countryside on a Vespa
  • Visits to Medieval Towns and Vineyards
  • Cooking experience in Chianti
  • Stunning panoramic views
  • Not confident? A driver will be provided!
  • Authentic regional Food & Wine daily
  • 5

    Tour Experience

  • 5


  • 4.5

    Quality of Amenities

  • 4.5

    Dining Experience

  • 4.5

    Quality of Accommodation & Grounds

  • 4.5

    Tour Locations

Important Information

  • Overview
  • Itinerary
  • Pricing / Date
  • Inclusions
  • Getting There
  • Accomodation

Enjoy the feeling of freedom travelling through the Tuscan countryside on a vespa! From the hillside of Cortona exploring this wonderful gem of a town; Cortona to Montepulciano, visitng cantinas dating back to the 13th century; Cortona to Lake Trasimeno where you will have the opportunity to take the ferry across to Isola Maggiore. Expand your culinary experience by participating in a traditional Tuscan cooking class with a local chef in Chianti and then enjoy lunch overlooking the vineyards. Don’t miss out on this Italian experience.

Remember this tour is for everyone! If you’re worried about riding a Vespa but would love the experience then simply let us know and we can organise a driver for you.

  • Saturday
  • Sunday
  • Monday
  • Tuesday
  • Wednesday
  • Thursday
  • Friday
  • Saturday


We transfer you to your accommodation and allow you to settle in and familiarise yourself with your new surroundings which will be “home” for the next 7 days. Dinner in Cortona.

Explore Cortona Hillside

Today we will spend the morning exploring the stunning countryside and Hillside of the Medieval Cortona by Vespa, the setting for the movie and book “Under the Tuscan Sun”. We will stop for lunch at a trattoria in Cortona to indulge in some local dishes. After lunch you will have some free time to explore and get to know this beautiful township; Visit the many boutiques, art galleries, stroll to the “high point” and visit Chiesa di Santa Margherita, where the Saint’s remains are encased high on the altar. Return to the villa by bike or car mid to late afternoon for a little relaxation by the pool before dinner in Cortona.

Siena & San Gimignano

We travel to Siena, a visit to the spectacular Piazza del Campo, where the famous bareback horserace is held. Visit Il Duomo and The Mangia Tower or simply stroll the streets and enjoy the ambience and the various delights Siena has to offer, from the little food stores which offer lots of tempting treats to the beautiful stores offering hand painted ceramics and leatherware. From there we visit San Gimignano for the afternoon. This is a beautiful medieval township which really is a step back in time. This township houses many stores which offer a very broad range of painted ceramics as well as leatherware and alabaster. Two wonderful piazzas where you can simply stroll, visit a museum or climb a tower for a breathtaking view of the Val d’Elsa, or simply sit and enjoy a delicious gelato. Dinner in Cortona

Cortona to Montepulciano by Vespa

Enjoy stunning panoramic views as we ride from Cortona to Montepulciano located in the Val d’Orcia; this township is a true gem, great shopping, wonderful Trattoria’s, Cantina’s and Sulumeria’s for wine and cheese tastings of which we will enjoy as a group. After a wine tasting and lunch you will have some free time to explore Montepulciano on your own. Mid afternoon we will ride back to the villa for some relaxation time before dinner. Location of dinner will be decided on the day.

Vespa ride to Lake Trasimeno

Today we spend the day exploring the beautiful Lake Trasimeno by Vespa. Departing from Cortona we will travel approx. 15 – 20km before arriving at our lunch spot. We will then explore the lake area before catching a ferry across to Isola Maggiore where we will spend a few hours. We will travel back to the villa mid afternoon for some free time before dinner in Cortona

Chianti & Cooking Experience

This morning we will head towards the Chianti area and spend the morning with Laura in a 15th century Italian Cottage where she will impart her knowledge and passion of cooking. During the course of this day we will interact with the winemakers of this family run establishment. Lunch will be enjoyed overlooking the spectacular undulating landscape of vineyards and olive groves.

Location for dinner will be decided on the day.

Tour Free Day

Today you may choose to “stay in” enjoy the pool and relax. Alternatively you may choose to visit a local township where you can spend the day “exploring”. We will arrange transportation to and from our local train station. Dinner in Cortona.


After a leisurely breakfast we transfer you to the local train station for your onward travels.

Tour Cost: USD $3,550 per person, twin share.
Single Occupancy : USD $300



Available for commencement every Saturday through to 6th October.

Minimum 2 participants required for departure.

Available for commencement every Saturday from 4th May through to 7th September

Minimum 2 participants required for departure.

Chat to us more if you are looking for a tour outside these dates.


Tour cost includes:

  • Accommodation for 7 nights’ in a Tuscan villa (one accommodation for the duration of the tour) with all modern facilities and a fantastic swimming pool with stunning views of the surrounding countryside and the Medieval township of Cortona on the hilltop. The apartments within the villa are fully self-contained and will be entirely for your use, either one, two or three bedrooms, spacious living area and fully equipped kitchen, bathroom and laundry facilities.
  • Bi-Lingual hosts for the duration of your tour
  • 5 day tours to itinerary locations
  • All breakfasts (continental)
  • Welcome pack of local delicacies and seasonal fruit
  • Complimentary bottle of wine & beer
  • 5 Light lunches (eg.pizza/panini/ salad)
  • 7 dinners (a-la-carte) at a local trattoria or restaurant. One/two glasses of wine with dinner
  • Vespa’s for Vespa touring days only
  • Cooking Experience in Chianti
  • All travel to and from tour locations as detailed on itinerary
  • Ferry tickets for travel to Isola Maggiore
  • Wine tasting at selected vineyards/ establishments
  • Maps for all itinerary locations
  • Transfers to local train station or Cortona on tour free days
  • Transfers to and from the local train station on your arrival and departure days
  • Free access to Wi-Fi at the villa

What is not included in tour cost:

  • All items not detailed in inclusions
  • Personal spending
  • Tickets for museums/monuments
  • All transfers other than to the local train station


We are located near Cortona; 2.5 hours by regional train from the main train station in Rome (Roma Termini) and 1.5 hours by regional train from the main train station in Florence (Santa Maria Novella).


Please contact us for prices.


If you are already in Italy connection to either Roma Termini or Firenze Santa Maria Novella train stations is easily accessible via other train stations.

Either of these two major cities are a good option for your arrival into Italy and then travel to our location. We will meet you at our local train station Camucia-Cortona and will transfer you, via vehicle to the villa, which is a short drive into the countryside.

Arrival from Rome Airport:

  • Take the Leonardo Express Train from Rome Airport to Roma Termini Train Station
  • (This is a 30min journey and will cost approximately 15 Euro)
  • From there take a regional train to Camucia-Cortona
  • (This is a 2.5hr journey and will cost approximately 15 Euro)

Arrival from Florence Airport:

  • Take the bus that goes to Firenze Santa Maria Novella Train Station
  • (This takes approximately 30mins and will cost approximately 15 Euro)
  • From there take a regional train to Camucia-Cortona
  • (This is a 1.5hr journey and will cost approximately 13 Euro)

Located in the valley, near the historical centre of Cortona (approx. 10km), the accommodation, a Tuscan villa with old world rustic charm, is your home base for the duration of the tour. Unpack, settle in to your own private apartment and commence your Tuscan experience.

Set on wonderful grounds with a spectacular pool and all modern facilities, including laundry, it overlooks the Val di Chiana and the historical centre of Cortona. On your tour free days take advantage of the country setting, pick fruit from the trees, stroll through the lush Italian countryside or simply enjoy reading a book by the pool under the Tuscan sun.

Learn More About Accommodation >

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Well informed, well-paced tour that presented Tuscany as we expected it to be. Very informative, great food & wine. Highly recommended.

- Daryl & Lesley - Australia

We have totally enjoyed the tours of Tuscany experience and believe Ines and Monique have given us an unforgettable journey of their love for the Tuscan & Italian culture, with professionalism and friendship that is hard to compare with. It is rare that you can say that your holiday experience totally surpass your expectations, which were set very high by the information documentation supplied. When Tours of Tuscany says ‘let us take you on this journey’ they meant it.

- Brad & Lucie - Western Australia - Australia

Get in touch with us

Australia (+61) 400 191 511

Italy (+39) 331 4253965


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