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Italy - Puglia - The Beautiful South - Guided Road Cycling Holiday

Holiday Highlights

  • Ostuni – the White City and its Arab influenced architecture
  • Ride around the Heel of Italy along from Otranto to Gallipoli
  • Enjoy the sights at Alberobello famous for its Trulli houses
  • 3 UNESCO heritage sites: Lecce, Alberobello & Matera
  • Savour the deep reds of Salento and the crisp whites of Locorotondo
  • Superb regional cuisine, savoured after a day’s ride

View Holiday Schedule

Day Description Distance Ascent Meals
1 Arrival: Bari Airport Non Riding Day    
2 Santa Maria di Leuca to Otranto 34 Miles / 55 Kms Approx. 650 Metres approx. B L  
3 Otranto to Lecce 37 Miles / 60 Kms Approx. 300 Metres Approx. B L  
4 Visit Lecce Ostuni to Alberobello 25 Miles / 40 Kms Approx. 600 Metres Approx. B  
5 Alberobello Loop Ride 40 Miles / 65 Kms Approx. 750 Metres Approx. B L  
6 Alberobello to Matera 46 Miles / 75 Kms Approx. 650 Metres Approx. B L  
7 Matera Loop Ride 56 Miles / 90 Kms Approx. 900 Metres Approx. B L  
8 Departure: Bari Airport Non Riding Day   B  

Key: B - Breakfast, L - Lunch, D - Dinner

For more information download our trip notes

Holiday Information

Brand new for 2017 we are bringing you the opportunity to explore the Puglian region of Italy on 2 wheels. Puglia is located in the southeast in what is commonly known as the heel of Italy’s boot, and also its best kept secret...until now!.
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.
Our route starts in Ostuni, in the heart of the Trulli region, before heading to Lecce, the 'Florence of the South'. From here we head south along the Adriatic coast and the heel of Italy then looping back up north along the Iolian coast and cross country through ancient olive groves, whitewashed hilltop villages toward Alberobello, a town made up of ‘Trulli’ houses.
Our final destination for this week is Matera, just over the border into Basilicata, but famous for the 'Sassi', a whole town's houses carved out of the soft rock where people have lived for over 9,000 years!

For more information download our trip notes

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8 days

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Holiday Summary

8 days
Estimated flight price:


Bike Hire:
Single Room:

Holiday Details

Place to place

7 nights hotels & masserie

6 days riding

Breakfasts and 5 lunches

Guided and vehicle support

Group airport transfers

Luggage transfers

Customer Photos


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

Skedaddle Italia Srl is registed Tour Operator in Italy. Registred No. 406, VAT No. 03592410926. Reg. office: Via Caravaggio 10, Assemini, 09032, Sardinia, Italy

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