Bike Across Southern Italy

A Magical Sea-to-Sea Exploration of Undiscovered Lands

Download a Detailed Itinerary

Our comprehensive itineraries are a one-stop-shop for all the delightful details of our carefully crafted tours, including:

  • A thorough daily itinerary
  • Details for exact accommodations
  • What to expect
  • Travel planning tips

Please provide your contact information so that we can say “benvenuto”. After submitting the form, you will be able to download the itinerary immediately.

Nuns in Southern Italy at sunset
A person standing in a cave in Belvedere, Italy


This tour was featured in Outside Online's "Trips of a Lifetime" in 2004.

Once you have a trip confirmed, we will feed you a steady diet of additional pre-departure information that includes: How to train, prepare, pack and all the wonderful, inspirational and practical things you want and need to know before you go! Our Travel Advisors will be available to help plan your pre- and post-tour travel.

  • Van Support
  • Expert, bilingual guides
  • Guided walking tours of the Trulli of Alberobello, the Sassi of Matera and the “Certosa” monastery in Padula
  • Wine tasting
  • Shuttle at the end of the tour

What’s Included

  • Use of our exclusive carbon road bike, La Classica Ribelle (or Equivalent Carbon Road Bike)
  • Garmin Edge Explore GPS loaded with the GPX tracks of your rides
  • Two water bottles
  • Saddle bag with repair kit
  • Optional: map holder on handlebar 

Pedal Options

  • Flat pedals
  • Half-toe pedals (without straps)

What’s Not Included

  • Helmet
  • Optional: clipless/SPD pedals with shoes
  • Optional: your own saddle
  • All accommodations
  • All breakfasts
  • 3 lunches
  • 7 dinners

Discover an Italy you never imagined on this magical cycling trip. Deluxe accommodations await at the end of each day’s adventure on our cycling tour. We’ll spend a night each in Palinuro and Maratea, two of Italy’s most beautiful coastal towns, so you can enjoy the area’s forests and beach coves, friendly residents, and welcoming trattorie and seafood restaurants. We will visit Matera, one of the oldest continuously inhabited cities in the world. It is a magical place that contains evidence of human settlements dating back to the Palaeolithic period, in natural caves that were carved into the rock. When you visit Matera, which is located on a limestone plateau in Basilicata, you will encounter deep fissures, ravines, rocks, and caves that make you feel like you are entering a nativity scene.



Jun 2-10
Sep 9-17


May 17-25
Jun 13-21
Sep 27-Oct 5
From $6,380 PP 9 days / 8 nights
From $6,430 PP 9 days / 8 nights
$1,575 Optional Single Supplement
Any of our tours can be made private. Contact us to learn more.

Confirmed tours are dates that have been selected by us that have a very high probability of reaching the minimum group size for us to run the tour and for you to receive the best Ciclismo Classico experience. These tours are confirmed as much as a year in advance, compared to our regularly scheduled tours which are confirmed around 90 days prior to departure.  When you place your deposit for a confirmed tour, you have the green light to make your pre and post travel plans and even book your flight with our personal guarantee that your tour will run!

Optional Single Supplement

If you are traveling alone, this optional single supplement will guarantee you a room to yourself at each hotel. The cost of a single room is often more than half the price of a shared room, so this additional supplement reflects that increased cost for each night over the course of the trip.