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Guided Tour

The Italian Job

15 days / 14 nights • Guided • 2099 mi / 3358.4 km • 55 - 85 °F / 12.8 - 29.4 °C

A travel through history in the home of some of the world's most influential art and sculpture and dining. Experience the beautiful lifestyle of Italy with its unique culture, cuisine and countryside. The best of Italy experienced on a motorcycle.

Transform your journey into an exhilarating Harley Tour by selecting one of our incredible Harley models such as the Harley-Davidson Road Glide Special, Harley-Davidson Street Glide Special, Harley-Davidson Road Glide Ultra, Harley-Davidson Electra Glide Limited, Harley-Davidson Heritage Softail Classic, or for a different riding experience, choose from our sport touring models like the BMW R 1250 GS, Harley-Davidson Pan America 1250, BMW R 1200 RT, BMW R 850 GS, BMW R 1250 GS Adventure, or KTM 1290 Super Adventure.

  • Treviglio

    day 1

    Treviglio - Arrival

    0 mi / 0 km

    Arrival to Milan or Bergamo Airport. In the afternoon motorcycle check-in at EagleRider location and after a quick orientation of the bikes, briefing with our tour leaders. Welcome Dinner at the restaurant of EagleRider location and overnight stay in Treviglio.
  • Treviglio - Siena

    day 2

    Treviglio - Siena

    239 mi / 382.4 km

    Your amazing Italian adventure begins today with a ride across the vast agricultural flat land called “pianura padana” into Emilia Romagna region. A scenic ride over the Appennini mountains will drop us right into the heart of Pisa, home of the world-famous leaning tower and Piazza dei Miracoli. After snapping a few memorable photos and savoring our first bites of Italian food we will resume our ride and head towards the hills where we will stop in beautiful Volterra, one of the oldest Etrurian settlements in the area. A scenic cruise through the Chianti hills, Italy’s most known red wine, will take us to Siena, Citta` del Palio”, one of Italy’s most beautiful cities. Walking through its “contrade” (districts) will set you back a few centuries, till the medieval era, soaking in its rich historical and cultural qualities. Siena, declared a UNESCO’s world heritage site, is home of the first world bank still operating these days. Overnight in Siena.
  • Siena - Fiumicino

    day 3

    Siena - Fiumicino

    150 mi / 240 km

    Today we saddle up and enjoy the ride through Tuscany’s enchanting wine country towards Montalcino and along its endless vineyards. After a coffee break surrounded by some of Tuscany’s most sensational scenery, we continue our ride to Lake Bolsena (Lazio region) where we will take our lunch and then ride all the way to Fiumicino where we overnight.
  • Fiumicino - Sorrento Peninsula

    day 4

    Fiumicino - Sorrento Peninsula

    250 mi / 400 km

    Leaving Fiumicino, we ride along the coast of the Tyrrenian sea going from the Lazio region into Campania, we reach the heart of south of Italy, the Sorrento Peninsula and Amalfi coast, world famous as the most beautiful and romantic place. Our hotel is overlooking the enchanting panoramic views of the Gulf of Naples and the Vesuvius. From its large and sunny terraces, you will be able to enjoy breathtaking views of the sea, the woods and the olive groves providing the best moments for us to enjoy for the next 2 days. Overnight in Sorrento Peninsula.
  • Sorrento & Amalfi Coast - day free

    day 5

    Sorrento & Amalfi Coast - day free

    0 mi / 0 km

    Our first day of relaxation! Amalfi: a UNESCO’s world heritage site, one of the only 4 ancient marine republics, gives its name to the coast where it rises, a magical place where the scents of lemons and ciders will welcome you. The Amalfi Coast is a popular tourist destination for the region and Italy as a whole, attracting thousands of tourists annually. In 1997, the Amalfi Coast was listed as a UNESCO World Heritage site. Today we will have the option to visit the island of Capri, easily reachable by hydrofoil or Pompeii, the ancient Roman city at the foot hill of the Vesuvius, the eruption of which completely buried it back in the year 79 A.C. The local food is nothing short of exceptional so make sure to taste and enjoy some of the local specialties.Overnight in Sorrento Peninsula.
  • Sorrento Peninsula - Maratea

    day 6

    Sorrento Peninsula - Maratea

    220 mi / 352 km

    Today’s ride will be memorable as we cruise south along the coast and then through the Cilento peninsula with its beautiful evergreen hills and charming small villages. We’ll reach Maratea, a beautiful southern town perched on the hilly coastline, also known as "the pearl of the Tyrrhenian Sea" and "City of 44 churches" for its numerous churches, chapels and monasteries. It was in this region (Basilicata) that the name “Italia” was born, previously of Greek origin, later extended to the rest of the peninsula.
  • Maratea - Alberobello

    day 7

    Maratea - Alberobello

    170 mi / 272 km

    The morning views from Maratea are jaw dropping but soon we will leave those behind to enter the heart of the Basilicata region. We will rise a brief coast to coast from the Tyrrenian sea to the Ionian Sea, perhaps savor some seafood along the way and ride towards today’s destination: Alberobello. worldwide famous for its Trulli, the traditional Apulian dry stone huts with their unmistakable conical roofs.
  • Alberobello - Matera

    day 8

    Alberobello - Matera

    80 mi / 128 km

    In the late morning we will ride to Matera and enjoy a walking guided tour to visit in the famous Sassi di Matera. The Sassi originated in a prehistoric troglodyte settlement, and these dwellings are thought to be among the first ever human settlements in what is now Italy. Many of them are little more than small caverns, and in some parts of the Sassi a street lies on top of another group of dwellings. In the 1950s, as part of a policy to clear the extreme poverty of the Sassi, the government of Italy used force to relocate most of the population of the Sassi to new public housing in the developing modern city. Until the late 1980s the Sassi was still considered an area of poverty, since its dwellings were, and in most cases still are, uninhabitable and dangerous. The present local administration, however, has become more tourism-orientated, and it has promoted the regeneration of the Sassi as a picturesque touristic attraction with the aid of the Italian government, UNESCO, and Hollywood. Overnight in Matera
  • Matera- Vieste

    day 9

    Matera- Vieste

    210 mi / 336 km

    With the magic of Matera still in our minds we ride north. Our lunch stop will be in Melfi right outside a medieval castle, host of an archeology museum. Due to its central location in the Mediterranean, South of Italy was at different times inhabited by different civilizations all of which left several traces. After visiting the museum It’s time to ride out and into the Puglia region. There is an estimated 50 to 60 million olive trees in Puglia and the region accounts for 40% of Italy's olive oil production. A gelato stop in Manfredonia and afternoon ride to Vieste, Gargano’s promontory most eastern town.
  • Vieste - Montegranaro

    day 10

    Vieste - Montegranaro

    220 mi / 352 km

    Now riding along the Adriatic Sea, we leave the Puglia region behind, crossing the Gargano, into the Molise and Abruzzo region. We’ll stop for lunch along the way and reach our hotel with plenty of time to relax at our hotel in the town of Montegranaro where we overnight.
  • Montegranaro - Nocera Umbra

    day 11

    Montegranaro - Nocera Umbra

    210 mi / 336 km

    From Montegranaro we say goodbye to the sea and head inland cruising through the Monti Sibillini National Park into the Umbria region, nicknamed by its inhabitants “the center of the world”. We arrive in Assisi, town of San Francis, Patron of Italy, and birthplace of the Franciscan Fathers. Perched on the hillside of Mount Subasio, you can admire the Basilica di San Francesco. In this magical town we will take a long lunch/sightseeing break and after that we will ride to our hotel in the rolling countryside of Umbria region.
  • Nocera Umbra - Firenze

    day 12

    Nocera Umbra - Firenze

    130 mi / 208 km

    Today will be a short ride from Umbria back to Tuscany but no rush, there is always time for an espresso break somewhere along the way and more tasteful Italian delicacies. We reach Firenze in the early afternoon in time to make some plans for our well-deserved day off. There are so many sightseen options in Florence that it might take the time of a few aperitifs to plan it out…
  • Firenze - day free

    day 13

    Firenze - day free

    0 mi / 0 km

    Day free in Firenze. Firenze was a center of medieval European trade and finance and one of the wealthiest cities of that era. It is considered the birthplace of the Renaissance and has been called "the Athens of the Middle Ages”. From 1865 to 1871 the city was the capital of the recently established Kingdom of Italy. The Florentine dialect forms the base of Standard Italian, and it became the language of culture throughout Italy due to the prestige of the masterpieces by Dante Alighieri, Petrarch, Giovanni Boccaccio, Niccolo` Macchiavelli and Francesco Guicciardini. The city attracts millions of tourists each year, and the Historic Centre of Florence was declared a World Heritage Site by UNESCO in 1982. The city is noted for its culture, Renaissance Art and Architecture and monuments. The city also contains numerous museums and art galleries, such as the Uffizi Gallery and the Palazzo Pitti, and still exerts an influence in the fields of art, culture, and politics. Due to Florence's artistic and architectural heritage, it has been ranked by Forbes as one of the most beautiful cities in the world.
  • Firenze - Treviglio

    day 14

    Firenze - Treviglio

    220 mi / 352 km

    Sadly, it is our last day of riding, nonetheless an amazing one full of great sceneries riding from the Tuscan hills into Appennini area. Time for our final stretch, all the way to the EagleRider headquarter. We return our bikes and get ready to share some stories and good memories at our farewell dinner. We now wish you safe travels back and hope to see you soon for another great Italian ride.
  • Treviglio - Departure

    day 15

    Treviglio - Departure - Arrival

    0 mi / 0 km

    Check out and departure from Italy. Be sure to let us know if you would like to spend few days in Milan or keep your EagleRider motorcycle a bit longer and we will make the arrangements for you.

starting at $4,984

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$4,984 per person