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Road Bike Cycle in Italy

On this road cycling trip we cross the breadth of Italy from the Adriatic to the Mediterranean. We take a beautifully scenic route passing through the regions of Le Marche, Umbria and Tuscany. Along the way we pass medieval towns, lakes, mountains, vineyards and Roman ruins. Each evening you can relax and reflect on the day's cycling over a glass of local wine and fine Italian cuisine.

Tour Highlights

  • Coast to Coast - A bike ride from the Adriatic to the Mediterranean
  • Sense of achievement - Cross Italy on two wheels
  • Historic - Stay in medieval walled towns, see Siena and Roman ruins
  • Scenery - Enjoy nature with wonderful views along the ride


Itineraries on some departure dates may differ, please select.

Show more
  • 1
    Trip starts in Bologna Airport; drive to Pesaro

  • 2
    Ride to the picturesque medieval walled town of Urbino

  • 3
    Cycle across the Apennine mountains into Umbria

  • 4
    Ride through Umbria to Tuscan hilltop town of Montepulciano

  • 5
    A classic ride through Tuscan countryside to Siena

  • 6
    Free day in Siena. Optional Chianti Classico cycling

  • 7
    Scenic cycle ride to the Mediterranean coast

  • 8
    Trip ends in Pisa Airport

Trip notes

Each departure date has its own dedicated trip note, detailing all you need to know about that trip. Whether you've already booked, or weighing up your options, please choose carefully the relevant itinerary for you.

We have the following different versions of the Cycle Italy Coast to Coast trip available at present.

Please select a date:

Customer rating:
Cycle Italy Coast to Coast
Why Book this trip
Unlike many other operators, we include the hire of your bike in the overall cost of the holiday: you don't need to bring your own or pay extra to hire one locally. We also provide a support vehicle, spare parts and take care of day to day bike maintenance. All you need bring is your own helmet.
Included meals 7 0 0
Breakfast Lunch Dinner
Bus, Bicycle
7 nights Standard Hotel
Trip Staff
Driver(s), Explore Tour Leader / Cycle guide
Cycling Information
On this tour we cycle 414 km over 5 days (an average of 83 km per day) with a further 65 km available. The terrain is generally undulating. We cycle mainly on quiet, minor tarmac roads with some short sections on main roads. A support vehicle accompanies the rides throughout the tour except on the rest day. We have graded the route as challenging.
Included Bike
18, 20 or 22 gear Focus Culebro or Cayo road bikes with drop bar.
Group Size
Generally 10 - 16