Journeys worth taking

Florence to Rome

Florence to Rome by Vespa

From Scratch

A unique way to see the rolling Tuscan country side


Hotels & Agriturismos



Trip Details

Self Guided


$3,080 per person



Pygmy miles


Pygmy miles
Practical info



It's out in the country where you will find the real Italy. The roads turn behind rolling hills and the air smells like garlic, earth and flour. People are in no hurry here. Lunches last longer and shops close earlier. 

For those with an adventurous spirit and up for a challenge, this can be a trip of a lifetime

Each day, you will ride a vespa between 50 to 75 miles. Far enough that you can reach Rome in 10 days, but slow enough to appreciate the changes in the culture, landscape, wine and food. Throw in handpicked boutique hotels, eco friendly agriturimos and a customized itinerary suited to your interests, and you have yourself a uniquely-you Tuscan Experience.  


slow enough to appreciate the changes in the culture, landscape, wine and food



Ride through Tuscany, Umbria and Lazio, experiencing a variety of cultures, hill-top cities and landscapes along the way.


Enjoy wine tasting at a Chianti Vineyard and a special "zero km" dinner.

Ancient Ruins

There is so much freedom. Not only the feeling of freedom that comes from riding on two wheels, but the freedom to explore a weathered castle, tumbling fortress or ancient forum.

And also

  • We also have an extensive list of extra excursions that you can take including private wine tasting, gallery tours, cooking classes and guided city tours.
  • Not to mention, relaxing at charming agriturismos with a good book and an organic wine. 


Maybe not all roads lead to Rome, but certainly many of them in Italy do. The Strade Statali, or state highways, are labeled SS in Italy and SS1 through SS8 all lead to Rome. On this journey you will be traveling through three distinct regions of Italy - Tuscany, Umbria and Lazio. You will mostly travel on smaller SR (Strade Regional) and SP (Strade provincial) roads. These roads carry far less traffic than Strade Statali or the even larger Autostrada (A1, A2, etc) and allow time to enjoy the beautiful scenery of provincial Itlay.  

You will begin your journey in Florence, in the heart of the Tuscan region. Tuscany is known as the birthplace of Italian Renaissance and stretches from Aulla in the north to Pitgliano in the south. The major cities in the area include Florence, Siena, Pisa, Luca and Cortona. Probably the most famous, Florence is home to two world class galleries: the Uffizi and the Academy, both essential stops on any trip to the city. Several famous wines are produced in the area as well. The Chianti region, known for making the DOCG wine with the iconic red rooster, and Montepulciano, whose wine makers may only claim to produce wine from Montepulciano if their grapes are grown within 7 kilometers of the tiny city, are two good examples. 

To the East of Tuscany lies Umbria, which is often known as the green heart of Italy because it contains dense forests, hidden castles and areas foraged for expesnive truffles. On this itinerary, you will drive through a small portion in the far west of Umbria to reach Orvieto, a mighty hill top town with a sprawling cathedral. You will then continue on into Lazio. In Lazio lay the bulk of ancient ruins and much of the history of Roman antiquity. The capital city is Rome, however many other exciting cities lay in wait here including Civita di Bagnoregio, Viterbo and Tivoli. Rome is home to a vast array of cultural icons like the Vatican, St. Peters and the Collesium. Because of the confluence of roads mentioned before, we have arranged for travelers to arrive into Tivoli, 30 miles to the east. 




How do we plan your trip?

The first thing we do is establish a base itinerary. There are a number of routes to take that will get you to Rome. Our suggested itinerary (listed below) includes a variety of experiences and hits several highlights that we feel are unique to the regions. We pay close attention to historic towns, fortresses and culinary ambitions and also to the rich agricultural heritage of Italy - the agriturismos are a perfect setting for kicking back with a bottle of wine and a good meal. This itinerary is well suited for adventurous couples looking for something different. If you are group of friends traveling together, we have a similar itinerary that places you closer to the center of most cities. Please let us know your preference when you inquire. 

We also offer customized itineraries (additional fee may apply). Maybe you are a huge Etruscan fan and want to see the ruins near Bolsena. Or maybe you can’t get enough of everything wine and we can develop your itinerary around the wines of Chianti, Montepulciano and Viterbo. Or maybe you just want to relax and find some harmony outside of a hectic office space. In that case, we know some killer secret hot springs that will make the stress melt away. Whatever your passion is, we will enthusiastically help you feed it. 

After we figure out your base itinerary, we fill in the finer details. We have a list of private and group tours in the cities and towns that you visit. Generally, we recommend to leave the itinerary plenty loose. That way you have plenty of time to indulge in your whims and make spontaneous decisions. 



Arrive in Rome and catch a connecting first class rail to the renaissance city of Florence. You will be met at the train station and transferred via private driver to your centrally located hotel. After unpacking, you will join your experienced vespa trainer for your first day of training. The vespas will be available in an area without heavy traffic and you will drive through the city surroundings for approximately 4 to 5 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. The next stops depends on your preference, either a trip to a lux winery for tasting or the suggested route to the city of Greve in Chianti, where you will stop for lunch at a famous butcher shop and learn about their sustainable practices (lunch not included).



Today’s focus is the wine of the Chianti Region including the Chianti Classico, Chianti Reserve and Supertuscans. Included is a wine tasting at Rocca di Castignoli which can be arranged directly with the tasting room. Other wineries will be recommended based on your level of interest. (Overnight in Rocca di Castagnoli)



After breakfast, you will take off on your Vespa - bound for the circular fortress city of Monteriggioni. Explore the town at your leisure and ride into Siena in the afternoon.



Today you will explore the city of Siena, an ancient rival of the Florentines. Many sites await your discovery, including the bustling Piazza del Campo, the storied Siena Cathedral and the Basilica of San Domenico. Specific recommendations made based on interest. (Overnight at La Villa Str)



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, which is perched on a forested hill. A stop in Pienza’s Renaissance city center, a UNESCO heritage site, is also possible. After a full day, wind down with a 6 course meal at your agriturismo (included).



Today, after waking up with a beautiful view of the hilltop city, you will explore Montepulciano.
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. Recommendations based on interest. (Overnight at San Martino)



Riding is on tap for today. After breakfast, you will hit the backroads for a scenic drive through the Etruscan city of Chiusi and down to Orvieto. Situated on tufa rock, Orvieto was once a stronghold for popes. In the 16th century, Pope Clement VII built an impressive 65 meter well so that the city could withstand a siege similar to one that occurred in Rome in 1527. After spending time in Orvieto, you will ride to your agriturismo, located outside of the town of Sorano.



Today, you can visit the towns surrounding your agritursimo. Of note is the Jewish quarters of Sorano and Pitigliano and Etruscan ruins. Alternatively, you can relax at your Agriturismo with a good book and some organic wine.



Today you will explore one of the most iconic hill-towns of Italy. Rising out of the badlands, a medieval city sits precariously on eroding rock. In the past, a dirt path snaked its way steeply to the mouth of the village from the valley floor below. However, that path was destroyed and now a single paved path, the only way in and out of the city, sits in its place. The city varies in population, from 12 in the winter, to 100 in the summer. After exploring the city, you will hit the road again. Your destination is Viterbo. At it’s heart sits a winding medieval center. Take your time; exploring the ancient cobbled streets. Arrive at your spa hotel and unwind with a cocktail at their outdoor bar. You will stay at a working Olive orchard, 10 minutes from the city center.



Outside of Viterbo sits Lago Vico, whose waters sit in the basin of Vico Volcano. The lake feeds many thermal springs in the area, including the famous Bullicame, which was mentioned in Dante’s Inferno. We can recommend some “Wild Spas” that are hidden on the outskirts of the city. With your Vespas, you will be sitting in the same healing waters that the popes did more than a half a millennium ago in no time.



Today you will visit one of the first resort towns in the world. With ancient villas, cascading waterfalls and lush forests blanketing the surrounding hills, Tivoli is a feast for the eyes. After an arranged drop off of your Vespas, you will hop on a train to reach the city center of Rome. You will be picked up at the train station and transferred to your hotel in Rome City Center.



After Breakfast, you will be picked up at your hotel and driven to the train station. From here you will board a high speed train to the airport. Additional days in Rome can be arranged at your discretion.

Pygmy miles

Pygmy Miles Total

Motorized Vehicle
3080pygmy miles

Base Miles

You earn 1 Pygmy Mile for every dollar you spend with us.

795pygmy miles

Vespa Distance

You earn 3 miles for every mile you travel by Vespa (miles are approximate).

500pygmy miles

Complete a challenge

Getting yourself some A to Z will be an adventure. If you are up to the challenge, we will reward you with 500 bonus miles.

250pygmy miles

Slow Travel Bonus

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 her.

Total Pygmy Miles

4625pygmy miles



Dedo Boutique Hotel


The Dedo Boutique Hotel is located in the 3rd floor of a classic building, featuring modern rooms and is a 5 min walk from Santa Maria Novella Station and a 10min walk from Ponte Vecchio & Florence Cathedral.

Rocca di Castagnoli


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 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 twentieth century (walking distance from the historic center). The rooms are tastefully decorated with respect for the aesthetic and historical origins of the building.

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.

Sant Egle


100% of the energy used comes from renewable sources. The heating and hot water is provided by solar panels, fireplaces and a condensing boiler. The rainwater is used for irrigation of the farm. The breakfast and dishes from the restaurant are made from organic produces, many from organic farms in the area and Sant Elge's own Farm.

Relais Villa Rossi Danielli


Rooms are located in a farmhouse on a working olive orchard with over 14,000 olive trees on the property. This small hotel de charme has been completely restored, but it is great to see that its rural origins have been respected in communal areas and that the furnishings refer to the original use of the house. Materials used are natural and prized: terracotta floors, the handles and lampshades made from wrought iron, table tops from marble.

Mama's Home Rome


Marzio F. Campi, hospitality entrepreneur, reinvented and redesigned the historic home of his family, a palace of the 14th century, creating a mix of traditional and new style with bathroom products directly from Sbordoni, bathroom line signed by Maison Martin Margiela and toiletries (MALIN + GOETZ): ceilings with wooden beams, ancient stones coming together with steel, among antique mirrors and home automation technology.

Practical info


Price per person based on double occupancy: $3,080 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 rental
  • Vespa pick-up from Tivoli and return to Florence
  • One day training around Florence
  • One day guided tour from Florence to Chianti
  • Baggage transfers
  • Maps, guidebook and suggested route.
  • 12 Breakfasts
  • 1 Wine Tasting
  • 3 Zero Km dinner
  • 12 Nights of handpicked accommodation at Agriturismos and boutique hotels
  • 1st class train ticket Florence to Rome (or vice versa)
  • Private transfer from Florence train station to hotel
  • Train from Tivoli to Rome
  • Private transfer from Rome train station to hotel
  • Incidentals
  • Alcohol
  • Travel and medical insurance (mandatory)
  • Flight to and from Italy


Service categories

Pygmy Itineraries

From Scratch

You can either build your vacation on top of our itinerary, or we will build one for you from scratch (extra fee may apply). We're here to help either way. We have an extensive list of extra excursions that you can take including private wine tasting, gallery tours, cooking classes and guided city tours are also possible. 


not available

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

Challenge Level

Technical Ability

Level : High

Mental Strength

Level : Medium

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.