A link to reset your password has been sent to your email

Guided Cycling Tour in Italy

Join Italy Cycling Tour in this guided cycling tour exploring Puglia in South Italy! This tour is designed for those who like to explore the cuisine, culture, and history of the Apulian region while riding through the amazing hilltop towns and seaside ports. The focus is on getting away from the crowds and closer into the real Southern Italy, with selected authentic accommodation ready to make you sleep like a baby at the end of the days.

Key information

  • Trip type: Guided
  • Lodging: Point to Point
  • Terrain: 90% asphalt, flat to hilly terrain with some gentle climbs and descents
  • Starts in: Matera
  • Ends in: Lecce
  • Difficulty level: Moderate (Cyclist needs to have a good level of fitness, the terrain is mostly hilly or unpaved but they will ride on flat terrain sometime, 31-45 miles per day)
  • Total Distance: 237 Miles / 382 Kilometers
  • Type of bike: Road bike
  • E-bike: Available to rent / 290 EUR


  • 6 days with guided cycling
  • Explore Southern Italy on a bike
  • Luggage transfers and a support van is available
  • There's a local expert bike escort throughout the tour
  • Breakfasts, lunches, and dinners with beverages daily
  • Selected 3 or 4-star authentic lodging
  • 7 nights' accommodation

Skill level

  • Intermediate


6 cycling days in English
The organizer also speaks: Italian
Group size: 2-16 participants
Hide all


You will be staying in a double room with private facilities. Italy Cycling Tour guarantees 3 or 4-star hotel or bed-and-breakfast accommodation based on the room availability.


  • Hotel San Domenico al Piano
  • Hotel Place Matera


  • Hotel Ramapendula
  • Hotel Olimpo
  • Hotel Astoria
  • Hotel Victor Country


  • Hotel 33 Baroni
  • Hotel Fly


  • Hotel Terminal - Caroli
  • Hotel Approdo


  • Hotel Minerva
  • Balconi sul Mare
  • Masseria Uliveto


  • 8+ Hotel
  • Hotel delle Palme
  • Hotel President
  • Vico della Cavallerizza


Day 1: Matera

Your guide will meet you at Bari Karol Wojtyła Airport (BRI), then, it is a presentation and transfers to your accommodation in Matera. Recognized by UNESCO as a World Heritage Site, Matera is unique in the world because the original town was dug into a canyon. Its caves were inhabited up until the late 1950s. This city has been used as the set of many movies including Mel Gibson’s "The Passion of the Christ". Matera is also a lively city and is also awarded the title of European Capital of Culture for 2019. Presentation of the itinerary, dinner, and overnight stay in Matera.

  • Meals: Dinner

Day 2: Matera - Alberobello (74 kilometers / 46 miles)

Cycling across the countryside between Basilicata and Puglia. Today, your destination is Alberobello. The UNESCO site of Alberobello is undoubtedly the capital of the Trulli: its historic center is integrally constituted by these rather particular white pyramidal structures that make it so famous and identifiable.

The best way to experience Alberobello is getting lost in the cluster of white dry stone huts, unique in the world. Visit an organic cheese factory set in the middle of a stunning landscape among grazing cows, olive groves, and almond trees. Savor a cheese tasting that will include mozzarella, provolone, and other local specialties (light lunch). Dinner is at a typical grill restaurant and overnight stay is in Alberobello.

  • Meals: Breakfast, light lunch, and dinner

Day 3: Alberobello round trip (70 kilometers / 43 miles)

It is a round trip from Alberobello, crossing the Itria Valley (a sub-region situated between Brindisi, Taranto, and Bari, it's also known as the Trulli Valley), in a bright landscape of vineyards, olive groves, and vast gentle slopes. Before return back to your accommodation, you will have the possibility to admire and taste Capocollo, a typical cold cut of the Apulia region and "Slow Food Presidium", directly in the company (light lunch). Overnight stay is in Alberobello.

  • Meals: Breakfast and light lunch

Day 4: Alberobello - Manduria - Gallipoli (65 kilometers / 40 miles)

From Alberobello, crossing Ceglie Messapica, you cycle up to Manduria. Founded by the Messapians, it still bears vestiges of its ancient past including the megalithic walls, the remains of the moat, and the necropolis.

Here, you will stop at one of the oldest cooperative Winery of Puglia, for tasting “Primitivo wine of Manduria” and other typical products (light Lunch); you will visit the museum of primitive wine and admire the old works machines. After a little transfer, you will reach the nice city of Gallipoli. Overnight stay is in Gallipoli.

  • Meals: Breakfast and light lunch

Day 5: Gallipoli - Leuca (53 kilometers / 33 miles)

You will ride from Gallipoli up to the extreme heel of Italy. Today’s destination is Leuca, the southernmost tip of Puglia. The stage starts from Gallipoli the "beautiful city" in Greek, a very charming and lively holiday destination. Not to be missed is the old town with its ramparts and defensive walls around a kilometer and a half, to defend the city against attacks from the sea.

Along your journey, you will stop for a local picnic before arriving in Leuca. Here, you can admire "the meeting" between the Ionian Sea and the Adriatic Sea, and the lighthouse, and sanctuary which welcome you at the end of the day. The sanctuary of Santa Maria de Finibus Terrae, located on a promontory within walking distance from the lighthouse, with its height of 48.60 meters and its location at 102 meters above sea level, is among the most important in Italy. Overnight stay is in Leuca.

  • Meals: Breakfast and light lunch

Day 6: Leuca - Otranto (60 kilometers / 37 miles)

Today, the sea will be the leitmotif of the journey. You cycle northwards along the Adriatic coast to Otranto, the top eastern point of the Italian and a city that was for centuries the meeting point of different cultures and the crossroads between the Mediterranean and the Orient.

Enjoy peaceful panoramic overview: nestled among the cliffs above the sea, this road is a huge balcony that looks onto the Adriatic Sea. The sea is extraordinarily beautiful, a sparkling blue. The rocky bays, where one can dip, are a continuous temptation difficult to resist. Before arriving in Otranto which is famous for its beautiful Cathedral and the great Aragonese Castle, you stop for a delicious meal at an excellent seafood restaurant overlooking the sea. Overnight stay is in Otranto.

  • Meals: Breakfast and lunch

Day 7: Otranto - Lecce (60 kilometers / 37 miles)

The final step will take you up to Lecce one of the most elegant and refined towns of southern Italy, including its Baroque churches, noble palaces, and the Roman amphitheater. Pedal along the Adriatic coast, through the Alimini Lakes and their unique Mediterranean bush, to reach "the Florence of South": Lecce.

Halfway, you will meet Acaya, a charming town characterized by massive and impressive walls, towers, and walls built in order to protect the coast and the hinterland against the incursions of the Ottoman Empire. Enjoy a typical lunch and overnight in Lecce.

  • Meals: Breakfast and lunch

Day 8: Lecce

There will be transfer service to Bari Karol Wojtyła Airport (BRI) or Brindisi Airport (BDS).

  • Meals: Breakfast


This tour is taking place in Southern Italy covering Matera, Alberobello, Leuca, Otranto, Gallipoli, and Lecce.


The following meals are included:

  • Breakfast
  • Lunch
  • Dinner
  • Drinks

The following drinks are included:

  • Water
  • Alcoholic beverages

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

Things to do (optional)

You can book guided walking tours in Matera, Alberobello, Otranto, Gallipoli, and Lecce for an additional cost during the holiday.

What's included

  • 6 days of guided cycling
  • Local expert bike escort throughout the tour
  • Luggage transfers
  • Support van shuttles
  • Breakfasts, lunches, and dinners
  • Beverages at meals (local wine and water)
  • 7 nights' accommodation

What's not included

  • Airfare
  • Airport transfers
  • Guided walking tours (750 EUR)
  • Tickets and entrances
  • Tourist taxes

How to get there

Recommended Airports

Cancellation Policy

  • A reservation requires a deposit of 40% of the total price.
  • The deposit is non-refundable, if the booking is cancelled.
  • The rest of the payment should be paid 10 days before arrival.
8 days / 7 nights
from --
Pricing information
  • Based on 3 pax: 1,995 EUR per person
  • Based on 5 pax: 1,755 EUR per person
  • Road bike hire: 490 EUR per person for 6 days
Minimum group size

This trip requires a minimum of 2 participants

Select your package:

For this organizer you can guarantee your booking through BookCyclingHolidays.com. All major credit cards supported.

Why choose BookCyclingHolidays.com

Largest Selection
Friendly Customer Service
Offers for every budget
Best Price
Don't miss out, join our mailing list and get updates & special offers!
Served by www:8000

Logging out

of Tripaneer websites