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9 Days In the Heart of Italy Guided Motorcycle Tour in Tuscany and Umbria

Rome, Lazio, Italy

Tuscany Motorcycle Tour Italy

Welcome to a great journey into the heart of Italy! Five days experiencing the challenging, curvy backroads of Tuscany and Umbria, as well as one rest day to explore the beautiful town of Siena. Also, there will be time to discover beautiful art-filled cities, such as Orvieto, Pienza, and Civita di Bagnoregio. 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 Rome which allows easy planning to extend your visit to this fabulous city should you want to.

Key information

  • Terrain: asphalt
  • Bike: personal or rental bike (BMW, Moto Guzzi, Ducati, Harley Davidson models)
  • Mileage: 1,178 kilometers / 732 miles
  • Daily rides: 106 - 267 kilometers / 66 - 166 miles
  • Riding gear: Not included: helmets, motorcycle boots, armored jackets, rain gear, and gloves
  • Meals: all breakfast, welcome and farewell dinners in Roma, 1 dinner in Siena, 1 wine tasting and dinner in Siena, and 1 dinner in Orvieto

Meet the guides

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  • Starts and ends in Rome
  • Visit the stunning Radicofani and medieval village of Bagno Vignoni
  • Ride along the beautiful roads in San Gimignano, Chianti, Greve in Chianti
  • Visit Crete Senesi, San Giovanni d’Asso, Pienza, Città Della Pieve
  • Cruise the beautiful off-beaten small roads of the Chianti Region
  • Enjoy wine tasting and homemade dinner in Siena
  • A support vehicle is provided
  • 8 nights accommodation

Skill level

  • Intermediate
  • Advanced


6 riding days in English
The organizer also speaks: Italian
Group size: 8-12 participants
Airport transfer included: Leonardo da Vinci–Fiumicino Airport
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Throughout the tour, you will stay in four-star hotels; 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.


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.


Day 1: Welcome to Rome!

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, Hear The Road Motorcycle Tours Italy convenes in the bar of the hotel for a "Meet and Greet" with your tour colleagues. Then you 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, you 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. Overnight is in Rome.

Highlights: Meet your motorcycle, meet your guide, meet your fellow riders, and welcome dinner.

Day 2: Rome to Siena (267 kilometers / 166 miles)

You 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, you 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.

You arrive in Radicofani where you 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, you visit the tiny village of Bagno Vignoni, another fantastic little medieval village with its characteristic piazza boasting an enormous 16th-Century thermal bathtub is truly fascinating!

Your first dinner in Siena is courtesy of 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 Magical Italy. Dinner is courtesy by Hear The Road. 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 kilometers / 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, you 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.

Your first stop is San Galgano where you visit 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, you 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, you 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, you 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, you will enjoy a great wine tasting, and then you will put your legs under the table for another superb homemade dinner, courtesy by Hear The Road. Yes, today is a day that you’ll remember fondly when you are back home! Overnight is in Sienna.

Highlights: San Gimignano, Chianti, Greve in Chianti, wine tasting, and homemade dinner.

Day 4: Free day in Sienna

There is so much to see and do in Siena, so we chose this as your 'free' day, where you can visit Siena on your own. 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 amphitheater, 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, an 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 Cathedral 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 a historic building, you will be able to do some wonderful shopping.

For those who prefer to ride, Hear The Road Motorcycle Tours Italy has organized an afternoon day ride led by Enrico that leaves from and returns to our hotel in Siena. Dinner is at your leisure. Overnight is in Siena.

Highlights: Siena at your pleasure.

Day 5: Siena to Orvieto (217 kilometers / 135 miles)

You leave Siena heading south towards the Crete Senesi, famous for its stunning moonscape. After a short break in the little medieval village of Trequanda, you 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, you saddle up again for a fantastic plunge on the winding roads of the "Green Umbria", heading towards Orvieto where you'll spend the next 3 nights.

Just to finish the day in the best possible way, you'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, San Giovanni d’Asso, Pienza, Città Della Pieve.

Day 6: Orvieto to Orvieto - Visit of Orvieto and Lake Corbara Loop (106 kilometers / 66 miles)

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

On the way to Todi, you visit the little hamlet of Titignano, with its wonderful square facing the Tiber Valley, but above all, you will ride the challenging road that the local call "La Strada Delle Mille Curve or "the road of 1000 curves!". Dinner is at your leisure. Overnight is in Orvieto.

Highlights: Orvieto, Prodo, "the road of 1000 curves", Titignano, Todi, Lake Corbara.

Day 7: Orvieto to Orvieto - Hot Spring Loop (174 kilometers / 108 miles)

Today is a day that you can call a relaxing day! From Orvieto, you head West towards Pitigliano where you 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 bike, you 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 you 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. Overnight is in Orvieto.

Highlights: Pitigliano, Saturnia Spa.

Day 8: Orvieto to Rome (167 kilometers / 104 miles)

It may be your last riding day, back to Rome, but certainly not an unforgettable day as you ride along some of the best roads of Umbria and Lazio. Your first stop is the historic Civita di Bagnoregio, an enchanted town, perched as if by magic, on a rock of Tufo. Your last lunch on the road is a picnic, yes you stop on the shores of Lake Vico surrounded by the Cimini Mountains, to devour panini padded with local prosciutto and cheese!

Then you wind your way back to Rome on more nice roads. After returning the bikes, you arrive at the hotel with time to freshen up before getting together for your "tour celebration" dinner, courtesy of Hear the Road. Overnight is in Rome.

Highlights: Civita di Bagnoregio, picnic on Lake Vico, farewell dinner.

Day 9: Departure day

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.

Motorcycle rental models

Motorcycle Class 1

  • BMW F800 R
  • Moto Guzzi V7

Motorcycle Class 2

  • BMW F750 GS
  • BMW F800 GT
  • Ducati Scrambler 800
  • Ducati Monster 797

Motorcycle Class 3

  • BMW F850 GS
  • Ducati Multistrada 950
  • Ducati Supersport

Motorcycle Class 4

  • BMW R1250 GS
  • BMW R1200 GS
  • BMW R1250 R
  • BMW R1250 RS
  • Ducati Scrambler 1100

Motorcycle Class 5

  • BMW R1250 GS ADV
  • BMW R1200 GS ADV
  • BMW R1250 RT
  • Harley-Davidson models: Softail Heritage / Ultra Limited / Road King / Road Glide / Road Guide Ultra / Street Glide

Motorcycle Class 6

  • BMW S1000 XR
  • BMW S1000 R
  • Ducati Multistrada 1260
  • Ducati Diavel

Motorcycle Class 7

  • BMW K1600 GLT


If you decide to rent the bike through Hear The Road Motorcycle Tours Italy, the following equipment is included: motorcycle rental with side cases, top case, tank bag, locks, and alarm. The bike rental prices include costs for public-liability insurance and insurance for any road assistance in case of break-down.

Please note that a deposit for damage, theft, and fire between 1,500 and 3,000 EUR is required for the rental bikes, depending on the bike you will rent. Each motorcycle has a damage deposit. This amount will be frozen on your credit card, but not cash. 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.

Support van

The van will be carrying a tool-kit for small repairs. You’ll be able to leave your cases (one suitcase plus one handbag per person) in the van, as well as any souvenirs you pick up along the way. The van also has a couple of seats that passengers might like to use if they feel they need a little rest from the bikes!

Skill level(s) required for this tour: intermediate to advanced


  • can ride for 3-4 hours
  • average riding experience
  • little assistance required
  • comfortable with extreme curves and leans
  • average experience with unsurfaced roads
  • steep ascents and descents


  • can ride for 5-6 hours
  • extensive riding experience
  • assistance on demand (if required)
  • experienced with riding a variety of motorcycles
  • comfortable with any terrain and weather conditions


Enrico Grassi


This tour will bring you to fascinating places in Tuscany and Umbria. You will have one free day in Siena to enjoy what the city has to offer.


Daily breakfast, welcome and farewell dinners in Roma, 1 dinner in Siena, 1 wine tasting and dinner in Siena, and 1 dinner in Orvieto are included in the package.

The following meals are included:

  • Breakfast
  • Dinner

The following drinks are included:

  • Alcoholic beverages

The following dietary requirement(s) are served and/or catered for:

  • Regular (typically includes meat and fish)
If you have special dietary requirements it's a good idea to communicate it to the organiser when making a reservation

What's included

  • Motorcycle rental with side cases, top case, tank bag, locks, and alarm
  • Welcome and farewell dinners in Roma
  • 1 dinner in Siena, 1 wine tasting and dinner in Siena, 1 dinner in Orvieto
  • 8 nights accommodation
  • Italian tour leader
  • Transfer from and to the airport
  • Courtesy van to pick up and leave the bikes
  • Support van where your cases will be carried (1 suitcase and 1 handbag per person) from Roma to Siena, Siena to Orvieto and Orvieto to Roma
  • 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's not included

  • A deposit for damage theft and fire, between 1250 and 2000 EUR is required for the rental bikes depending on the bike you will rent
  • 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
  • Travel insurance

How to get there

Recommended Airports

Arrival by airplane

Please book your flight to arrive in Rome, at Leonardo da Vinci–Fiumicino Airport (FCO). Transfer from and to the airport is included. Hear The Road Motorcycle Tours Italy will pick you up from the airport.

Airport: Leonardo da Vinci–Fiumicino Airport Airport transfer included: Leonardo da Vinci–Fiumicino Airport No additional charges. You can request this in the next step.

Cancellation Policy

  • A reservation requires a deposit of 20% of the total price.
  • The deposit is non-refundable, if the booking is cancelled.
  • The rest of the payment should be paid 30 days before arrival.
9 days / 8 nights
from --
Minimum group size

This trip requires a minimum of 8 participants


Start: Thursday April 29, 2021
End: Friday May 7, 2021

Tour information

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

Additional prices
  • 1 rider with Class 7 motorcycle in a shared twin room: 3,980 EUR
  • Single supplement: 490 EUR
  • Pillion: 2,330 EUR

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