Two riders on Harley-Davidson touring bikes on a country road in southern Italy
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14 nights · Treviglio, Italy · Motorcycle

The Italian Job (Guided)

A fully guided version: ride past the Leaning Tower of Pisa, then Alberobello’s trulli and Matera’s Sassi cave dwellings with a guided walking tour included – fourteen nights the length of Italy, welcome and farewell dinners bookending the road.

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From£5,074pp
Duration14 days
StyleGuided
Best suited toExperienced riders
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14 nights through Italy

The full length of Italy, guided. Fifteen days from Treviglio near Bergamo, fourteen nights and around 1,950 miles, with a tour leader, an orientation briefing, welcome and farewell dinners, and a guided walking tour of Matera included.

Tuscany opens it, and the first three days are the best known of the whole trip. Pisa and the leaning tower, Volterra and the Chianti hills lead to Siena, then Montalcino and Lake Bolsena towards Rome. The Amalfi Coast follows, with two nights on the Sorrento Peninsula and a free day for Capri or Pompeii, which is the right way to handle a stretch of road that rewards a slow pace.

The south is the part that surprises people. Maratea and the Cilento coast lead into Basilicata and Alberobello, a town of conical dry-stone trulli, then Matera, where dwellings carved into the ravine were lived in until the 1950s and the guided walk explains how. Melfi castle, the olive groves of Puglia and Vieste on the Gargano follow, then the Adriatic coast, the Sibillini mountains and Assisi, before two nights in Florence.

EAGLERIDER provides the motorcycle, the tour leader, all fourteen nights and the group dinners. Fuel, most meals and insurance are arranged separately, and prices are quoted in US dollars. The guided route is around 150 miles shorter than the self-guided version and takes a slightly different line through Puglia. For riders who want the whole of Italy without having to navigate a mile of it, this is the complete guided version.

Style
Guided
Duration
A fortnight (11-15 nights)
Region
Europe
Vehicle provision
Vehicle provided
Departures
May
Starts/ends
Treviglio, Italy
Support
Guide
Accommodation
Hotels
Suitable cars
Experienced riders
Vehicle
Motorcycle
Price basis
Per person, two riders with two bikes (operator Package 3), USD 6,722. Operator also prices one rider with one bike at USD 8,115 and two riders sharing one bike at USD 5,394 per person. Read from the operator page 14 Oct 2026.
Run by
Specialist Stradora partner

What's included

  • Guided group with tour leaders
  • motorcycle rental
  • nightly hotel accommodation
  • welcome dinner
  • farewell dinner
  • guided walking tour of Matera's Sassi
  • full inclusions list needs manual check

Not included

  • Fuel
  • insurance (optional add-on)
  • most meals
  • taxes and fees

Ready to drive it?

14 days, from £5,074pp

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