Journeys worth taking

Florence, Chianti, Siena and Montepulciano

The Authentic Taste of Tuscany by Vespa

From Scratch

Discover the authentic and off the beaten path of Tuscany


Boutique Hotels, Villas and Agriturismos


5 Nights

Trip Details

2 days with guide, the rest self-guided


$1,550 per person, based on double occupancy



Pygmy miles


Pygmy miles
Practical info



The story of Tuscany is best told by being enveloped in the culture and it's rich gastronomic traditions. The Vespa, authentically Italian, is your vehicle for discovery. 

You will start in Florence with a day of training, to get you acclimated to driving a Vespa in Italy. The next day, it's off to learn the secrets of the Chianti hillside and perhaps meet one of it's most gregarious characters - the butcher of Panzano. Afterwards, carry on to your accommodation for the evening, a 12th century castle that overlooks a bounty of Sangiovese grapes. You will then carry on to Siena and take a food tasting tour of the city, learning the difference between white and black truffles and why Tuscan bread is plain. Then it's off to the historic hilltop town of Montepulciano and your peaceful agriturismo. Here you will enjoy a six course organic vegeterian dinner - on this tour you get the meat and the potatoes. On the final day you return to Florence, stopping in the historic San Gimignano to witness the 14 towers that still stand tall in the city. 

View from Rocca di Castagnoli



Each day, you will take to the road and discover the true pleasure of driving with the Tuscan sun above and the fields of vineyards around you.

Ancient Ruins

You will stay in Rocca di Castagonli, which was built in the 12th century as a fortress. It now serves as a hotel and reception for wine tasting of it's great wine estate.


In each city you stop, culinary secrets and learning opportunities await. From wine tasting at Rocca di Castagnoli to a food walk in Siena. And let's not forget the tale of two extremes: a chance to eat at the famous Butcher of Panzanos and a 6 course organic vegetarian dinner.



The birthplace of the Renaissance, Florence is home to a vast array of art. Like walking through an open air museum, the city is strikingly beautiful from the Duomo at Piazza del Signora to Loggia dei Lanzi. Inside the hallowed walls of the Galleria dell'Accademia, you will find the world renowned David and a few blocks away, the Uffizi Gallery exhibits Botticelli’s “The Birth of Venus” and da Vinci’s “Annunciation.” 


A region, rather than a single town, known for the deep, full bodied Chianti Classico made from at least 80% Sangiovese grapes. There are several towns in the area worth noting including Greve, Panzano and Gaiole. 


The ancient rival of the Florentines, Siena is a city that has a rich medieval and renaissance history. At night, Piazza del Campo is a flourish of activities surrounding the central focal point of the square, the Gothic town hall, and Torre del Mangia, a skinny 14th-century tower. 


Lesser known than the other cities on the list, none the less this small hilltop town packs a scenic bunch. The is not far from the lunar landscape of the Crete Senesi and the beloved Val d'Orca featuring gently rolling hills, vineyards, cypresses and medieval hilltop towns. The wine is no slouch either, and it's Vino Noble di Montepulciano may only be produced within a 7km distance from the town. 






After unpacking, you will join your experienced Vespa trainer for your first day of training. The Vespa will be available in an area without heavy traffic and you will drive through the city surroundings for approximately two to three hours.


Florence to Rocca di Castagnoli

After a typical Italian breakfast, it’s a 50-meter walk to meet your guide. Your first stop is the Michelangelo Piazza, where a seemingly endless view of the city awaits. After cruising the hills for an hour or two, you will arrive for lunch at a famous butcher shop for a delicious family style meal. Your guide will then take you to your accommodation. Now comes the challenge, the rest of the trip is self-guided.

The evening’s focus is the wine of the Chianti Region including the Chianti Classico, Chianti Reserve and Super Tuscans. Included is a wine tasting at Rocca di Castignoli which can be arranged directly with the tasting room. Dinner at the attached restaurant features local and regional ingredients sourced depending on the season (Overnight in Rocca di Castagnoli)


Castagnoli to Siena

After breakfast, you will take off on your Vespa, passing by the circular fortress city of Monteriggioni on your way to Siena. Many sites await your discovery in Siena, including the bustling Piazza del Campo, the storied Siena Cathedral and the Basilica of San Domenico. At noon, you will take a shared foodie walk through the city and learn, among other things, how to distinguish between qualities of olive oil, why Tuscan bread is plain, the difference between black and white truffles and the secret properties of local honeys. (Overnight at La Villa Str)


Siena to Montepulciano

This may be the most beautiful ride of the entire trip. The area between Siena and Montepulciano is known as the Crete Senesi. The name is derived from the grey clay that gives you a feeling of riding on a lunar landscape. Also in this region is the Abbey of Monte Oliveto Maggoire, and Pienza, a UNESCO heritage site. Dinner is a 6 course organic, vegan affair – most of the ingredients are sourced directly from the farm.



Today, after waking up with a beautiful view of the hilltop city, you will explore Montepulciano on a privately guided tour. Don’t forget to try the robust Vino Nobile di Montepulciano, which can only be grown in a very restricted area 7 sq. km around the city. You can then choose to explore more of the city on your own, or relax at the oasis that is Fattoria San Martino (Overnight at San Martino).


Montepulciano to Florence

Riding is on tap for today. You will head back on a similar, but not the same route, that you drove into Montepulciano. You will also visit San Gimignano and its 14 imposing towers. After returning to Florence, it’s time to say arrivederci and depart your self-guided tour.

Pygmy miles

Pygmy Miles Total

Motorized Vehicle
2003pygmy miles

Adventure Miles

You received 1,550 miles for choosing Pygmy Elephant to help plan your trip. You also received 203 miles for driving 203 miles on a Vespa and 250 Challenge miles for completing the trip self guided.

125pygmy miles


By traveling slower and visiting areas that are often farther off the tourist radar, you are helping communities and businesses that would be missed if you stuck to the highway. A secondary benefit, is that the traveler receives a richer and a more comprehensive understanding of the culture that is hosting him or her.

Total Pygmy Miles

2128pygmy miles



Dedo Boutique HOtel


The Dedo Boutique Hotel is located in the 3rd floor of a classic building, featuring modern rooms and is a five minute walk from Santa Maria Novella Station and a ten minute walk from Ponte Vecchio & Florence Cathedral.

Rocca di Castagnoli

Gaiole in Chianti

Rocca di Castignoli is situated in the heart of Chianti. The winery is built in a former fortress form the 11th century, beautifully restored, keeping its essential architectonic components.

La Villa di STR


Located just outside to the city walls of Siena, the Villa is a charming liberty style residence dating from the early years of the 20th century (walking distance from the historic center). The rooms are tastefully decorated with respect for the aesthetic and historical origins of the building.

Fattoria San Martino


A secret of sorts, your first challenge will be to find this hidden gem. Located only a couple kilometers from Montepulciano, you are encompassed in a stylish, farm oasis. The food - organic; the views - sublime; and your relaxation - maxed out.

Practical info

Price per person based on double occupancy: $1,550 per person

This trip is self guided, so an adventurous mindset and previous travel experience is critical. We provide you with everything you need to be successful, but ultimately, it's up to you to complete this journey.


  • Vespa rentals
  • One day training around Florence
  • One day guided tour from Florence to Chianti
  • Maps, guidebook, suggested route and GPS data.
  • 4 Baggage transfers
  • 5 Breakfasts
  • 1 Wine Tasting
  • 1 Dinner at Rocca di Castagnoli
  • 1 Zero Km dinner at Fattoria San Martino
  • 1 Shared Foodie Walking Tour in Siena
  • 1 Privately Guided Tour in Montepulciano
  • 5 Nights of handpicked accommodation at Agriturismos and boutique hotels
  • Incidentals
  • Alcohol
  • Travel and medical insurance (mandatory)
  • Flight to and from Italy



not available

This trip can be done in all seasons, however to get the most out of it, we recommend avoiding winter. 


Self guided

Privately guided

You will receiving one day of training in Florence and will be guided to Rocca di Castagnoli on the second day. After that, the trip is entirely self-guided. 

Service categories

Pygmy Itineraries

The trip was designed and researched by Pygmy Elephant and we work closely with our local partners to make sure your trip meets your high expectations. Furthermore, this itinerary can be customized to fit your desires. We have an extensive list of additional experiences that you can take including private wine tasting, gallery tours, cooking classes and guided city tours are also possible. 

Challenge Level

Technical Ability

Level : High

Mental Strength

Level : Low

Physical Conditioning

Level : Low

Although we include two days of training in the itinerary, this should not be your first time on a vespa. You must be over the age of 25 and have a valid driver's license. In Italy, you are allowed to operate a 125cc scooter with a normal driver's license.

Talk to our Adventure Expert

Our Managing Director, Andrew, has been to over 40 countries in his quest for the perfect adventure. He has biked the death road in Boiliva, trekked 500 miles across northern Spain on the Camino de Santiago, cycled from Brussels to Florence and hiked the five sacred mountains of China. Pygmy Elephant is how he spreads his love for adventure and self discovery in the world.