Tuscany on a Vespa

Dates From
7 nights
8 days
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Experience Tuscany on a Vespa! Ride through the hills of Tuscany to iconic locations taking in the beauty of the region. Travel with locals as you indulge in regional food, wine and all things Tuscan.

Indulge in the freedom of travelling through the Tuscan countryside on a Vespa! From the hillside of Cortona exploring this wonderful town. Cortona to Montepulciano visiting cantinas dating 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 enjoy lunch overlooking the vineyards. A truly authentic Tuscan experience!

Please note this tour requires a minimum of two participants.


  • Accommodation for 7 nights’ in a Tuscan villa
  • Bi-Lingual hosts for the duration of the tour
  • Day tours to itinerary location.
  • All breakfasts, 5 lunches and all dinners (a-la-carte) at a local trattoria or restaurant. Wine included
  • Complimentary bottle of wine and beer
  • Vespa & guide for Vespa touring days
  • Ferry tickets for travel to Isola Maggiore
  • Cooking experience
  • Wine tasting at selected vineyards/establishments
  • All travel to and from tour locations as detailed on itinerary
  • 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


Day 1: Saturday - Arrival

We transfer you from our local train station to your accommodation and allow you to settle in and familiarise yourself with your new surroundings which will be ‘home’ for the next 8 days. Dinner in Cortona.


We will spend the morning exploring the stunning countryside and Hillside of 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. Return to the villa by Vespa mid to late afternoon for a little relaxation by the pool. Dinner in Cortona.


We visit San Gimignano for the morning. This is a beautiful medieval township; 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 enjoy a delicious gelato. After lunch at a local trattoria we will head back towards Siena. You will have the afternoon to explore Siena; a visit to the spectacular Piazza del Campo, where the famous bareback horse race is held or Visit Il Duomo,
The Mangia Tower or simply stroll the streets and enjoy the ambiance and the various delights Siena offers, from the little food stores with many tempting treats to the beautiful selection of stores/boutiques. Dinner in Cortona.


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 trattorias, cantinas and sulumerie for wine and cheese tastings. After a wine tasting and lunch you’ll have some free time to explore Montepulciano.
Return to the villa mid-afternoon for a short rest prior to travelling to a nearby property dating back to the 1500’s for a hands-on cooking experience with a local chef, Donatella, who has over 20 years’ experience researching and rediscovering ancient recipes and Tuscan cooking traditions. Savour the
dishes you have prepared with the chef including local wine.


Today we spend the day exploring the beautiful Lake Trasimeno area by Vespa. Departing from Cortona we will travel approx. 15 – 20km and then stop for a Caffè/gelato. We will then explore the lake area before taking the ferry across to Isola Maggiore where we will spend a few hours and enjoy
lunch at a restaurant overlooking the lake. Return to the villa mid-afternoon for some free time. Dinner in Cortona.

Day 6: Thursday - CHIANTI

A leisurely day of taking in the most amazing views, whilst driving through this most famous wine growing area of Tuscany. During the morning, we will visit the village of Castellina; we will enjoy a Caffè together after which you will enjoy free time to explore this village which offers a wonderful selection of varied stores. We will then visit a vineyard a short distance away, interact with the winemakers and savour lunch and a wine tasting whilst enjoying spectacular views of the vineyards and olive groves. Return to villa late afternoon. Dinner in Cortona.

Day 7: Friday - TOUR FREE DAY

You may choose to ‘stay in’ enjoy the grounds and relax, visit Cortona or another local township. Alternatively, you may choose from one of our additional activities: cycling tour, cooking experience, cheese making class, gelato making class, painting class, hot air ballooning. Dinner in Cortona.

Day 8: Saturday - Departure

After a leisurely breakfast, we transfer you to the local train station for your departure.


Starts Ends Price Status Book
04/05/201911/05/2019$4,150 p/p twin shareAvailable
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11/05/201918/05/2019$4,150 p/p twin shareAvailable
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18/05/201925/05/2019$4,150 p/p twin shareAvailable
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25/05/201901/06/2019$4,150 p/p twin shareAvailable
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01/06/201908/06/2019$4,150 p/p twin shareAvailable
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08/06/201915/06/2019$4,150 p/p twin shareAvailable
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15/06/201922/06/2019$4,150 p/p twin shareAvailable
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22/06/201929/06/2019$4,150 p/p twin shareAvailable
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29/06/201906/07/2019$4,150 p/p twin shareAvailable
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06/07/201913/07/2019$4,150 p/p twin shareAvailable
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13/07/201920/07/2019$4,150 p/p twin shareAvailable
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20/07/201927/07/2019$4,150 p/p twin shareAvailable
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27/07/201903/08/2019$4,150 p/p twin shareAvailable
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03/08/201910/08/2019$4,150 p/p twin shareAvailable
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10/08/201917/08/2019$4,150 p/p twin shareAvailable
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17/08/201924/08/2019$4,150 p/p twin shareAvailable
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24/08/201931/08/2019$4,150 p/p twin shareAvailable
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31/08/201907/09/2019$4,150 p/p twin shareAvailable
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Travel insurance
Entry fees to museums/galleries and other places wherever entry fees apply
All lunches and meals not specifically listed above.
All personal expenditure.