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Italy - Puglia - Self-Guided Leisure Cycling Holiday

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A self-guided cycling holiday discovering the heel of Italy's boot.

Holiday Highlights

  • Cycling through lush landscapes of ancient olive groves and vineyards
  • Exploring the UNESCO World Heritage town of Alberobello
  • Discovering the traditional Trulli houses of Puglia
  • Relaxing each evening in comfortable hotels in authentic towns and villages
  • Stopping at beautiful, sandy beaches with turquoise seas
  • Tasting delicious local products, like extra virgin olive oil and Primitivo wine

View Holiday Schedule

Day Description Distance Meals
1 Arrival into Bari Airport - Transfer to Altamura    
2 Altamura to Matera Long 31 Miles / 50 Kms - Short 23 Miles / 37 Kms B  
3 Matera to Alberobello 43 Miles / 70 Kms B  
4 Alberobello Loop 29 Miles / 47 Kms B  
5 Alberobello to Ostuni 29 Miles / 47 Kms B  
6 Rest Day Non-Cycling Day B  
7 Ostuni to Polignano sul Mare 33 Miles / 53 Kms B  
8 Departure from Polignano - Transfer to Bari Airport   B  

Meals: B = Breakfast L = Lunch D = Dinner | Please keep in mind the distances and ascent information provided are intended to be indicative and may vary from the actuals due to accommodation changes or when compared on different GPS devices and software

For more information download our trip notes

Holiday Information

This is a self-guided cycling holiday exploring the Apulian region of Italy, and dipping into Basilicata to discover Matera. Located in the Southeast, in what is commonly known as the heel of Italy's boot, this lesser-discovered region combines glistening ocean views, authentic Italian towns and lush olive groves, offering a cycling treat!
This interesting and eclectic region is steeped in history and has been governed by the Greeks, Romans and Spaniards over the centuries, each leaving their own distinctive mark, from local dialects and flavoursome cuisine to unique architecture.
Your cycle tour will take you into a region of stunning, unspoilt beauty. Starting in Altamura, located in the Murgia region and famous for its churches that have been carved out of the limestone rock, your first ride will take you to Matera. Crowned as the European Capital of Culture in 2019, Matera is famous for its Sassi quarter, now a World Heritage Site.  Riding on through ancient olive groves and narrow country lanes, you'll reach Alberobello, a town made up of Trulli houses where you'll stay for two nights.
After exploring this fascinating Trulli region you'll carry on to Ostuni, known as 'La Citta Bianca', thanks to it's pristine, white-washed buildings. Your rest day will offer the opportunity to jump on the train to Lecce, the "Florence of the South", where you'll discover awe-inspiring architecture and vibrant streets filled with wine bars. 
Heading north you'll soon reach the Adriatic coast, enjoying stunning coastal views and exploring the idyllic towns of Monopoli and Polignano a Mare. Your final destination, Polignano a Mare, boasts a charming old town, beautiful beaches and culture to boot, making it the ideal spot to reflect on your week of cycling.

For more information download our trip notes

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Departure Dates:

Duration: 8 days
Return: 16/05/2020

Prices From:

£845 p.p.

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Holiday Summary

8 days
Prices From:
Estimated flight price:


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Holiday Details

Place to place

7 nights hotel accommodation

5 days riding

1 rest day



Route notes and maps provided

Luggage transfers

Airport transfers

Minimum 2 people

Daily departures

Customer Photos


Ask about private departures and group bookings

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Skedaddle News, Views and Holiday Stories

Customer Story: Exploring the ‘heel’ of Italy

Setting off on their first ever cycling holiday, Tom and Gillian didn’t quite know what to expect! Luckily they came to the right place, and with the expert guidance of our team they were able to pick out the trip that was a…

The post Customer Story: Exploring the ‘heel’ of Italy appeared first on Skedaddle Blog.

Last Updated: 27/03/2019