Tuscany Motorcycle Tour

April 3 - 11, 2020

Welcome Riders!

A great journey into the heart of Italy. Six days experiencing the challenging, curvy backroads of Tuscany and Umbria, as well as one rest day to explore the beautiful town of Siena. But also time to discover beautiful art-filled cities, such Orvieto, Pienza, and Civita di Bagnoregio.

The tour includes 2 overnights in the Eternal City of Roma, 3 nights in the ‘World Heritage” city of Siena, and 3 nights in the Majestic City of Orvieto.

The scenic roads and rolling hills of Tuscany, Umbria and Lazio are what connect these amazing cities for 8 days of a magnificent experience.

Enjoying a lunch or a coffee in small villages along the way will endear you to the rural life and culture that Italy is so famous for.

The lovely 16th century Inn in Siena has a swimming pool overlooking Siena, the Wine Resort Hotel in Orvieto has an outdoor swimming pool, an outdoor Jacuzzi, a spa with whirlpool, Turkish bath, and sauna… nestled into the center of a wonderful winery with 4 star food.

Enrico Grassi, Tour Leader and Founder of Hear the Road has spent many hours discovering the riding routes and the extraordinary hospitality to leave you with a Holiday Adventure you will always remember with a smile.

The tour starts and ends in Roma which allows easy planning to extend your visit to this fabulous city should you want to.

*Harley-Davidson® models are available upon request!*





Art / History


Food / Wine


Tuscany and Umbria in a Glance
> Date/s: April 3 - 11, 2020
> Tour Grading:     
> Total Distance: 1.178 km – 732 miles
> Riding Days: 6
> Riding Hours per day: 4 - 6
> Longest riding day: 267 km – 166 miles
> Shortest riding day: 106 km – 66 miles
> Free Day: Siena
> Support Vehicle: Yes
> 9 days / 8 nights (6 riding days – 1 free day)
> Day 1 − “Welcome to Roma”
> Day 2 − Roma to Siena (267 km / 166 miles)
> Day 3 − Chianti loop ride (247 km / 153 miles)
> Day 4 − Free day in Siena
> Day 5 − Siena to Orvieto (217 km / 135 miles)
> Day 6 − Visit of Orvieto and Lake Corbara Loop Ride (106 km / 66 miles)
> Day 7 − Hot Springs loop (174 km / 108 miles)
> Day 8 − Orvieto to Roma (177 km / 110 miles)
> Day 9 − Departure day

Where We Ride – What We See – What We Hear


A private car will transfer you from the airport to the hotel where you will find your Hear The Road host Enrico, waiting to give you a warm Italian welcome.
Late morning/early afternoon arrival is recommended.

After you’ve put your luggage in the room and take a good refreshing shower, we convene in the bar of the hotel for a “Meet and Greet” with your tour colleagues. Then we are ready to go to pick up the bikes and bring them to the hotel garage.

Back to the hotel Enrico gives you a general briefing of the tour and will be very glad to answer to all your questions.

Finally we are ready to go all together to taste the “Welcome Dinner”, where you’ll learn more about what to expect for the next exciting week.

HIGHLIGHTS: Meet your motorcycle, Meet your guide, Meet your fellow riders, Welcome Dinner.

DAY 2:  ROME TO SIENA (267 km / 166 miles)

We head north towards Tuscia, an area once inhabited by the Etruscans. This is also one of Italy’s biggest hazelnut grove areas, the small nut that Ferrero magically transforms into the famous Nutella spread.

After a short break for your first good Italian coffee on the road in Civita Castellana, we get back on the bikes and ride, first the beautiful coastline roads that run along the shores of Lake Vico and Lake Bolsena, and then the scenic backroads of Val D’Orcia – a UNESCO World Heritage site.

We arrive in Radicofani where we stop for lunch. Radicofani is a stunning Orange Flag awarded town (The Orange Flag Award was an idea formed by the Italian Touring Club in 1998 with the aim of promoting tourism in lesser known places in Italy) which surrounds the base of a hill on which the majestic fortress has stood since 973AD.

On the way to Siena we visit the tiny village of Bagno Vignoni, another fantastic little medieval village with its characteristic piazza boasting an enormous 16th-Century thermal bathtub!

Your first dinner in Siena is courtesy by Hear the Road…you will be pampered by the delicious dinner that Mrs. Letizia, proprietor of a lovely 16th century Inn has prepared for you to celebrate your first riding day in the heart of Italy! 
OVERNIGHT IS IN SIENA (The hotel has an infinity pool with a spectacular view of Siena). 

HIGHLIGHTS: Tuscia Viterbese, Civita Castellana, Val D’Orcia, Radicofani, Bagno Vignoni, Homemade dinner.

DAY 3: SIENA TO SIENA – CHIANTI LOOP (247 Km / 153 miles)

Are you ready to be blown away by the stunning roads of Tuscany? Spectacular landscapes, art, first-class food and wine! In the first part of the morning we head south riding on roads that are a true paradise for motorcyclists: wide bends, scenic stretches of asphalt, incredible landscapes, miles of vineyards, and dozens of stately villas.

Our first stop is San Galgano where we vist its stunning Abbey without the ceiling, and the little church of Montesiepi home to our very own “sword in the rock.

Back on the bikes we reach the gorgeous hilltown of San Gimignano, a splendorous Medieval atmosphere enwrapped by its 13th-Century wall, also known as “la città delle torri” (the city of towers).
“A masterpiece of creative human genius, it is unique testimony to a past civilization, and as an exceptional exemplar of both architectonic complex and landscape, demonstrates significant passages in human history.” It is for such qualities that San Gimignano earned its place on the UNESCO World Heritage List in 1990. 

Back on the bikes we still cruise the beautiful off-beaten small roads of the Chianti Region heading north to Greve in Chianti, the birthplace of Giovanni da Verrazzano, the famous Italian explorer who first sailed into New York Bay.

Back in the saddle we head South to Siena, for more exciting kilometers along the sweeping roads of Chianti.

And the day is not yet finished…Back at the hotel we will enjoy a great wine tasting, and then we will put our legs under the table for another superb homemade dinner, courtesy by Hear The Road.

Yes today is a day that you’ll will remember fondly when you are back home!

HIGHLIGHTS: San Galgano Abbey, San Gimignano, Chianti, Greve in Chianti, Wine tasting and Homemade dinner.


There is so much to see and do in Siena, so we chose this as our ‘Free’ day, where you can visit Siena on your own.

The town of Siena
Start from Piazza del Campo, or – as the Italian simply call it – “Il Campo”, where the famous Palio horse-race is held.

The town is a trophy of Medieval Art, the most prolific period of Siena. The square has the shape of an amphitheatre, looking at the Palazzo Publico, a masterpiece of Civil Gothic architecture. The square is on a gentle slope, climbing gently towards the Fonte Gaia, by Jacopo della Quercia. Above the building you’ll see the Mangia Tower, antagonist of the nearby Cathedral.

The Civic Centre is only a few steps away from the religious part of Siena, where you can admire the gothic lines that merge with the Medieval architecture of the Duomo dell’Assunta, one of the most beautiful buildings of this period.

Around the Catheral there are several important buildings: the Palazzo Arcivescovile, the Spedale di Santa Maria della Scala (now the National Archaeological Museum), the Palazzo del Governatore, the Opera Metropolitana Museum, and the 14th century Palazzo Piccolomini, also known as Palazzo delle Papesse. And between a church and an historic building you will be able to do some wonderful shopping.

For those who prefer to ride, we’ve organized an afternoon day ride led by Enrico that leaves from and returns to our hotel in Siena.

Dinner is at your leisure.

HIGHLIGHTS: Siena at your pleasure.

DAY 5: SIENA TO ORVIETO (217 km / 135 miles)

We leave Siena heading south towards the Crete Senesi, famous for its stunning moonscape.

After a short break in the little medieval village of Trequanda, we continue on to the beautiful city of Pienza, considered to be the incarnation of a Renaissance utopia and an ideal city. Having obtained recognition as a UNESCO World Heritage Site in 1996, today it continues to show off to the world its refined and sophisticated Renaissance urban plan. Its spaces and perspective into its 15th-Century “piazze and palazzo” are organized according to the era’s ideals of rationality and humanism. 

After lunch we saddle up again for a fantastic plunge on the winding roads of the “Green Umbria”, heading towards Orvieto where we’ll spend the next 3 nights.

Just to finish the day in the best possible way, we’ll experience a classic “Umbrian Tasting Dinner”, washed down with local wines that the hotel produces from the vineyards that surround it. Dinner is courtesy by Hear The Road.
OVERNIGHT IS IN ORVIETO (The hotel in Orvieto has spectacular ‘spa’ amenities such as, an outdoor Jacuzzi, a spa with whirlpool swimming pool, Turkish bath, and sauna…Getting pampered is all part of the experience!).

HIGHLIGHTS: Crete Senesi, Trequanda, Pienza, Sarteano.


We spend the morning visiting Orvieto and then after lunch we ride the scenic roads that meander around Lake Corbara, till the medieval town of Todi.

On the way to Todi, we visit the little hamlet of Titignano, with its wonderful square facing the Tiber Valley, but above all we will ride the challenging road that the local call “La Strada delle Mille Curve”…”the road of 1000 curves!”.

Dinner is at your leisure.

HIGHLIGHTS: Orvieto, Prodo, “the road of 1000 Curves”, Titignano, Todi, Lake Corbara.

DAY 7: ORVIETO TO ORVIETO – HOT SPRING LOOP (174 km / 108 miles)

Today is a day that we can call a relaxing day!

From Orvieto we head West towards Pitigliano where we stop briefly to take in the sights of this beautiful walled-village, characterized by its parapets, ceramic tile roofs and multi-tiered buildings, perched on layers of red volcanic tufo stone.

Back on the bikes we ride the scenic roads of the Maremma Toscana, – land of the “butteri” (the typical local cowboy) and brigands – where each town and village boast origins lost in the mists of time, and then we reach the Terme di Saturnia (Saturnia Spa), where we spend a big part of the day immersed in the hot spring waters. 

On the way back to Orvieto we challenge again the scenic and surprising roads in the heart of Italy!

Dinner is at your leisure.

DAY 8: ORVIETO TO ROME (167 km / 104 miles)

It may be our last riding day, back to Rome, but certainly not an unforgettable day as we ride along some of the best roads of Umbria and Lazio.

Our first stop is the historic Civita di Bagnoregio, an enchanted town, perched as if by magic, on a rock of tufo.

Our last lunch on the road is a picnic…yes we stop on the shores of Lake Vico surrounded by the Cimini Mountains, to devour panini padded with local prosciutto and cheese!

Then we wind our way back to Rome on more nice roads.

After returning the bikes we arrive at the hotel with time to freshen up before getting together for our “Tour Celebration” dinner, courtesy of Hear the Road.

HIGHLIGHTS: Civita di Bagnoregio, Pic nic on Lake Vico, Farewell Dinner.


Time to say goodbye, shop for any last minute souvenirs, and pack your bags. After breakfast, guests will be transferred to the airport in conjunction with their departure schedule.

2020 Prices

* Motorcycle Models Rider in Shared Room Rider in Single Room Couple
Rider in Shared Room Rider in Single Room Couple
Motorcycle Class 1
€ 3.330 € 3.780 € 5.420
Motorcycle Class 2
BMW F750 GS - BMW F800 GT
€ 3.420 € 3.870 € 5.510
Motorcycle Class 3
€ 3.480 € 3.930 € 5.570
Motorcycle Class 4
BMW R1250 R - BMW R1250 RS
€ 3.520 € 3.970 € 5.610
Motorcycle Class 5
BMW R1250 RT
€ 3.550 € 4.000 € 5.640
Motorcycle Class 6
BMW S1000 XR - BMW S1000 R
€ 3.670 € 4.120 € 5.760
Motorcycle Class 7
€ 3.750 € 4.200 € 5.840
Own Motorcycle
€ 2.590 € 3.040 € 4.680

*Rented Motorcycle Subject to Availability

For currency converter click here


Ken & Gina B.

“My wife and I took the Umbria/Tuscany this August. The tour was fantastic. The other people in the group were great. The accommodations were first class. It was clear Enrico did his homework planning this tour.
As this was a motorcycle tour we road motorcycles. The rental bikes were all in good shape and we got exactly what we reserved. Enrico planned into the rides plenty of breaks either to eat, tour a small town or just relax and enjoy the scenery.
The riding was invigorating but as Enrico says on his webpage this is not a ride to learn how to ride a motorcycle. The Italians do not ride/drive like Americans and you will be riding like Italians. The riding is often quick paced and often on old Italian roads. Sometimes narrow curvy roads, sometimes cobblestone. Italians lane split and love to pass the vehicles in front of them. If you enjoy spirited riding you will love it.
With that said you will never be pressured to ride outside of your comfort zone. Enrico does his best to accommodate everyone. You can ride at your own pace. Often my wife and I would slow down to enjoy the scenery as other riders wanted to ride faster. Enrico would wait for us to catch up further down the road.
This was a great trip and my wife and I have been talking about how much…fun it was ever since.”

David & Arlene A.

“The Tuscany and Umbria tour exceeded our expectations!  Pictures alone don’t do it justice. Your jaw will drop at every bend of the road.  The scenery is unbelievable and every one of your senses will be stimulated. And while your jaw is open, take the time to shove some porchetta in it. It is “bunga bunga” for your taste buds.  You will not be disappointed. You must experience the countryside firsthand, and the best way is by motorcycle. Enrico is a first class guide and host.  I can honestly say that the worst part of the tour was coming home.  We miss Italy.  We miss Enrico!  We will be back soon to Hear The Road!”

Roger S.

“So you say to your friends “I’m going to Italy to ride a bike….in August….in Tuscany” and the first reaction is…..wow a crowded and hot summer on Italian roads!  But let me assure that it’s quite the opposite.  Not only did we feel like we had the entire Italian countryside to ourselves, we felt like we were in the best and most hospitable hands and places in the entire country!  Granted Italy is a special place, but really much of the credit goes to company founder and tour leader Enrico Grassi.  It takes a special skill to know the right road, the right detour, the right coffee shop to make you feel like you are both at home and away, a local and a special visitor and Enrico knows how to push all the right buttons.   From total ride time, to road conditions, to excellent views, great restaurants and accommodations, this tour has a little bit of everything!  You want to tour Rome and get some history, check!  You want to sit back in a piazza and relax over a nice meal and excellent wine, check!  You want to haul ass on a nice twisty road with open corner after corner after corner, check! check! check!  This was my first time riding in Europe and I don’t regret the tour choice one bit.  A great way to whet my appetite and keep me coming back for more!  Corsica, Sardinia here we come!  Ciao Enrico!!”

Joel & Bonnie K.

“My partner and I had been to Italy before, or taken a guided motorcyle tour. We were blown away. Enrico planned every day perfectly. The hotels were top notch, with a true taste of Italian style. We loved our room at Alta Rocca in Orvieto, with a view of the vineyards from our window and balcony. Our stay for three nights at Podera della Strega in Siena was storybook, with breakfasts every morning outside, overlooking the valley and Siena. Our host, Ms. Leticia, was fabulous.
The food was marvelous, from the multicourse meal and wine at the resort in Orvieto, to the roadside stops for paninis and cafe.
Enrico seems to know all the best roads in Italy. Endless twisties and tornanti (harpin turns) with breathtaking views.
And best of all was the comraderie of the group. Evening, after evening, of good food and wine with friends.
Take one of Enrico’s tours. I promise you will NOT be disappointed.”

Creation of the tour: Associazione Culturale Hear The Road.
Organization and marketing: Hear The Road srl.

Content not available.
Please allow cookies by clicking Accept on the banner

Minimum number of participants: 8

If the minimum number of participants isn’t reached the tour may be cancelled or run with a different format.

What is included:

  • only for those who have decided to rent their bike through us: motorcycle rental with side cases, top case, tank bag, locks and alarm. (A deposit for damage theft and fire, between 1.250 and 2.000 euros is required for the rental bikes depending the bike you will rent)
    WHAT IS THE DAMAGE SECURITY DEPOSIT ? Each motorcycle has a damage deposit. This amount will be frozen on your credit card, but not cashed. The deposit is your maximum liability for theft or damage to the vehicle. Please ensure that you have enough funds to cover  the damage deposit on your cards.
  • the bike rental prices include costs for public-liability insurance and insurance for any road assistance in case of break-down
  • welcome and farewell dinners in Roma.
  • 1 dinner in Siena, 1 wine tasting and dinner in Siena, 1 dinner in Orvieto.
  • accomodation: 2 nights including breakfast in 4-star hotel in Roma, 3 nights including breakfast in 4-star hotel in Siena, 3 nights including breakfast in 4-star hotels in Orvieto.
  • Italian tour leader.
  • transfer from and to the airport.
  • courtesy van to pick up and leave the bikes.
  • support van where we’ll carry your cases (1 suitcase + 1 handbag per person) from Roma to Siena, Siena to Orvieto and Orvieto to Roma. The support van will be not with the group on day 3, 4, 6, and 7.
  • a detailed Road-book with all the information you’ll need; a map with the itinerary well marked; the “Wordless Travel Book”, and a Hear the Road T-shirt.
  • Insurance covering most any medical issue during the trip including, doctors, ambulance, hospital and any appropriate family travel.

What is not included:

  • fuel for your motorcycle.
  • tolls on motorways.
  • entrance fees to museums or other sites.
  • gratuities and tips.
  • all meals and beverages except for the welcome and farewell dinners, 1 dinner in Siena, wine tasting and dinner in Siena, and 1 dinner in Orvieto.
  • flights to and from Roma.
  • We also suggest that anyone traveling abroad for one of our Tours consider purchasing  “Travel Insurance”. It can take the worry out of the unexpected situations that can arise in any travel plan. 

Terms of payment:

  • 800 € Deposit, to be paid, on reserving a place on the tour.
    (The deposit is totally refundable in case we don’t reach the minimum number of participants).
  • Balance, to be paid, 60 days before the starting date when you get confirmation from HEAR THE ROAD.

In case of cancellation:

If you decide to cancel the tour for whatever reason that does not depend on HEAR THE ROAD, these are the penalties that will incur:

  • up to 60 days prior to the starting date, HTR holds the deposit, that you can use for another tour in the same or in the following year;
  • between 59 and 10 days prior to the starting date you lose the deposit. HTR holds the balance that you can use for another tour in the same or in the following year.
  • from 9 days prior to the starting date you lose 50% of the total amount. HTR holds the remaining 50% that you can use for another tour in the same or in the following year.

By continuing to use the site, you agree to the use of cookies. more information

The cookie settings on this website are set to "allow cookies" to give you the best browsing experience possible. If you continue to use this website without changing your cookie settings or you click "Accept" below then you are consenting to this.