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8 Days in the Heart of Italy 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 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

  • Bike: personal or rental bike (BMW, Ducati, Moto Guzzi, Harley Davidson models)
  • Terrain: asphalt
  • Mileage: 969 kilometers / 602 miles
  • Daily rides: 98 to 257 kilometers / 61 to 160 miles
  • Riding gear: Not included: helmets, motorcycle boots, armored jackets, rain gear, and gloves
  • Meals: daily breakfast, welcome and farewell dinners, 1 dinner in Siena, 1 wine tasting and dinner in Siena, 1 dinner in Orvieto

Meet the guides

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  • Start and ends in Rome
  • Ride four to six hours a day for five days
  • 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
  • Enjoy wine tasting and homemade dinner in Siena
  • Support vehicle is provided
  • 7 nights accommodation

Skill level

  • Intermediate
  • Advanced


5 riding days in English
The organizer also speaks: Italian
The maximum participants in the group is 12
Airport transfer included: Leonardo da Vinci–Fiumicino Airport
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Throughout the tour, you will stay in four-star hotels.


Day 1: Welcome to Rome! (late morning / early afternoon arrival is recommended)

A private car will transfer you from the airport to the hotel where you will find your Hear The Road host, Enrico, waiting for you to give you a warm Italian welcome. After you’ve put your luggage in the room and take a good refreshing shower, you will convene in the bar of the hotel for a "meet and greet" with your tour colleagues. Enrico gives you a general briefing of the tour and he will be also very glad to answer to all your questions.

Finally you are ready to go to pick up the bikes and bring them to the hotel garage. Then you 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, welcome dinner.

Day 2: Roma to Siena (257 kilometers / 160 miles)

It’s 9 a.m., Saturday morning, the town is still sleeping. This is the perfect time to leave Rome without having to deal with its traffic. You will 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 Ronciglione, you will 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 973 AD.

On the way to Siena, you will 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. Overnight is in Siena. The hotel has a swimming pool.

  • Highlights: Tuscia Viterbese, Ronciglione, Val D’Orcia, Radicofani, Bagno Vignoni, homemade dinner.

Day 3: Siena to Siena - Chianti loop (226 kilometers / 142 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.

Your first stop is San Galgano where you visit its stunning Abbey without the ceiling, and the little church of Montesiepi home to Italy's very own "sword in the rock."

Back on the bikes, you will 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. A good panino, stuffed with the local prosciutto and cheese, at the Macelleria Falorni is a must!

Back in the saddle, you will 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, you will enjoy a great wine tasting, and then you will put your legs under the table for another superb homemade dinner. Yes today is a day that you’ll will remember fondly when you are back home! Overnight is in Siena.

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

Day 4: Free day in Siena

There is so much to see and do in Siena, so Hear The Road Motorcycle Tours Italy chose this as the free day, where you can visit Siena on your own. For those who prefer to ride, Hear The Road Motorcycle Tours Italy will organized an afternoon day ride led by Enrico that leaves from and returns to your hotel in Siena. Overnight in Siena.

  • Highlights: Siena at your pleasure.

Day 5: Siena to Orvieto (206 kilometers / 128 miles)

You will leave Siena heading south towards the Crete Senesi, famous for its stunning moonscape. After a short break in the little medieval village of San Giovanni d’Asso, you will 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 will saddle up again for a fantastic plunge on the winding roads of the "Green Umbria," heading towards Orvieto where you’ll spend the next three 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.

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 (99 kilometers / 61 miles)

You will spend the morning visiting Orvieto and then after lunch we ride the scenic roads that meander around Lake Corbara. On the way, you will visit the little hamlet of Prodo, with its wonderful square facing the Tiber Valley. Then, you continue on to Todi, which is remarkable for its historical and artistic heritage. Overnight in Orvieto.

  • Highlights: Orvieto, Prodo, Todi, Lake Corbara

Day 7: Orvieto to Rome (178 kilometers / 110 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 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 will 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 Roma on nicer roads. After returning the bikes, you arrive at the hotel with time to freshen up before getting together for the tour celebration dinner, courtesy of Hear the Road. This will be your last overnight in Rome.

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

Day 8: 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 models

Motorcycle class 1

  • BMW G650 GS, BMW F700 GS, BMW F800 R, MOTO GUZZI V7
  • 1 rider in a shared room: 3,050 EUR
  • 1 rider in a private single room: 3,430 EUR
  • Couple in a private room: 5,080 EUR

Motorcycle class 2

  • 1 rider in a shared room: 3,150 EUR
  • 1 rider in a private single room: 3,530 EUR
  • Couple in a private room: 5,180 EUR

Motorcycle class 3

  • 1 rider in a shared room: 3,250 EUR
  • 1 rider in a private single room: 3,630 EUR
  • Couple in a private room: 5,280 EUR

Motorcycle class 4

  • BMW R1200 GS ADV, BMW R1200 RT
  • 1 rider in a shared room: 3,280 EUR
  • 1 rider in a private single room: 3,660 EUR
  • Couple in a private room: 5,310 EUR

Motorcycle class 5

  • 1 rider in a shared room: 3,400 EUR
  • 1 rider in a private single room: 3,780 EUR
  • Couple in a private room: 5,430 EUR

Harley-Davidson models

  • Softail Heritage, Ultra Limited, Road King, Road Glide, Road Glide Ultra, Street Glide
  • 1 rider in a shared room: 3,400 EUR
  • 1 rider in a private single room: 3,780 EUR
  • Couple in a private room: 5,430 EUR

Motorcycle class 6

  • BMW K1600 GLT
  • 1 rider in a shared room: 3,470 EUR
  • 1 rider in a private single room: 3,850 EUR
  • Couple in a private room: 5,500 EUR


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 the bike you will rent. 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.

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.

The town of Siena

During the free day, you can explore the city 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, antagonist of the nearby cathedral. The Civic Center 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 an historic building you will be able to do some wonderful shopping.


Daily breakfast, welcome and farewell dinners in Rome are included in the price. You will also enjoy one dinner in Siena, one wine tasting and dinner in Siena, and one dinner in Orvieto.

The following meals are included:

  • Breakfast

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

  • Welcome and farewell dinners in Rome
  • 1 dinner in Siena, 1 wine tasting and dinner in Siena, 1 dinner in Orvieto
  • 2 nights including breakfast in 4-star hotel in Roma, 3 nights including breakfast in 4-star hotel in Siena, 2 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 it’ll carry your cases (one suitcase plus one handbag per person) from Rome to Siena, Siena to Orvieto and Orvieto to Rome. The support van will be not with the group on day 3, 4, and 6
  • A detailed road-book with all the information you’ll need, a map of Central Italy, the “Wordless Travel Book”, a courtesy mobile phone with 10 EUR of credit 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

  • 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 Rome
  • Travel insurance (Hear The Road Motorcycle Tours Italy suggests that anyone traveling abroad for one of their tours consider purchasing travel insurance. It can take the worry out of the unexpected situations that can arise in any travel plan)

How to get there

Recommended Airports

Arrival by airplane

Book your flight to arrive in Rome, at Leonardo da Vinci–Fiumicino Airport (FCO). Transfer from and to the airport is included. The organizer 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 60 days before arrival.
8 days / 7 nights
from --


Start: Friday April 3, 2020
End: Friday April 10, 2020

Tour information

This tour requires minimum 8 riders. 


Pricing information
  • Get one free night in Rome if you book by January 2019.
  • The price packages below show options for motorcycle class 1 and bring your own bike. If you are interested in other motorcycle models, please send Hear The Road Motorcycle Tours Italy an inquiry.

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