the boot's heel

Cycling Level


8 days 7 nights

7 days B&B accommodation
from £1,181 per person (sharing a twin/double room)


If you wish to enquire about this tour please contact us on +44(0)7936 458564 email

Guided: minimum 6 people
Custom dates for groups of 6 or more 

5 stages / 1 guided walking tour
Total distance: 330 km Total climb 2900 mts
average mileage: 66 km/day
average climb: 600 mts/day

Puglia is our easiest tour, its coasts and plains perfect for relaxed rides. A landscape of century-old olive trees, amazing meadows and coastal routes reflect a peculiar light. From the Greeks to the Normans, the Arabs to the Spaniards, this region has been a busy crossroads that has left behind striking art bearing witness to those that have lived here. The Romanesque and Baroque old towns are architectural jewels and, as Italy’s first producer of vegetables, olive oil and wine, the local cuisine is just as inventive as is delicious. Fresh ingredients and a legendary cooking ability combine to give each meal a story to tell. The local wines are numerous so will only mention the superb red Primitivo di Manduria.


our price Includes:

  • 7 nights B&B accommodation in Masseria and 3 star hotel

  • Transfers from and to Bari airport

  • Baggage transfers throughout the tour

  • Walking tour of Matera with licensed guide

  • Wine tasting near Lecce

  • On-call assistance

  • Daily maps and cue sheets

  • Cycling guide

  • Full van support throughout the tour

The itinerary

Day 1:
Arrival Bari
We meet you at Bari airport for transfer to the hotel located in the ‘I Sassi’ district (Unesco WHS) of Matera. A vast assembly of dwellings mostly carved in the stone, ‘I Sassi’ have been inhabited since the Paleolithic Age. In the 1900s living conditions had become so unhealthy so as to force the Italian government to build new housing. Its renaissance began in the 90s with residents restoring the homes in order to move back. It has since gained international popularity, thanks also to several films set here such as Pasolini’s ‘Gospel According to Matteo’ and Mel Gibson’s ‘Passion of Christ’. Where only a few decades earlier people once lived in uttermost poverty, luxury hotels have now sprouted.  

Day 2:
Today we take a walking tour with a licensed guide that will include a visit to the two ‘Sassi’ (Sasso Caveoso and Sasso Barisano) ending at the Duomo located at the town’s highest point. The tour lasts 2.30 hrs but be warned, there will be many stairs to climb. 

Day 3:
Stage 1: Matera-Fasano 75 km - 600 mts total climb
Today we take an easy ride and head toward the Adriatic coast crossing the Murge hills, a luminous landscape of wheat fields and meadows in full blossom. We cross two charming towns where we can take a break for some gelato and refreshments. Our accommodation for the next 3 nights is in a Masseria located only 2 km from the beach. The Masseria are old farmers’ mansions, typical of Puglia, that have been transformed into prestigious lodgings. 

Day 4: 
Stage 2: Fasano-Alberobello-Fasano 64 km - 700 mts total climb
Today’s cycling is set in the Valle d'Itria. After an early climb to Selva di Fasano we reach Alberobello. Along the way we will see the Trulli, the perfectly preserved cone shaped stone dwellings that give a fairytale look to the valley. We take a walk in this fantastic setting rich in small artisan shops. On a narrow rolling back-road flanked by dry stone walls we reach Martina Franca, a remarkable example of well preserved Baroque architecture where we take some time at a café to savour the local delicacies and the charming surroundings. From here the ride is downhill and we return in plenty of time for a swim before dinner.

Day 5:
Stage 3: Fasano-Ostuni-Fasano 58 km - 400 mts total climb
Our tour moves to the Adriatic Coast and the Roman ruins of Egnatia. After reaching the beach resort of Rosa Marina, we embark on a path that follows the course of the ancient Roman ‘Via Traiana’. The road will gently rise and after a few switchbacks, we will see the dazzling whitewashed walls of Ostuni before us. Rightly named ‘la Città Bianca’, Ostuni presents a wonderful mix of architecture, a legacy of its many rulers. We stroll in the maze of alleys up to Piazza Grande and have lunch beneath the Cathedral’s shadow.

Day 6:
Stage 4: Fasano-Cellino S. Marco 80 km - 400 mts total climb
Today we leave Fasano and climb in the shade of pine trees to the walled village of Cisternino. The remaining journey is quite easy, with winding back-roads amongst olive trees, the plains of Puglia’s best wine country and historical towns with remarkable Norman castles. Our ride ends with a wine tasting after which we drive to the magnificent Baroque city of Lecce. The mouthwatering local specialties are hard to resist so we will have time for shopping. We resume our drive to our next Masseria just outside of Otranto ending a long day with a much longed for dive in the Masseria’s pool.  

Day 7:
Stage 5: Otranto-S. Maria di Leuca 53 km - 800 mts total climb
The Salento is a peninsula that extends between the Adriatic and Ionian seas and our final ride is set on its rolling Adriatic coast. Leaving Otranto, the coast becomes rugged and the road clings to the rock that allows breathtaking views of wild scenery, stone watchtowers and charming beach resorts. We reach S.Maria di Leuca and climb up to the Finibus Terrae Sanctuary (Land’s End) where our ride ends. From the top of the Cape the view stretches over the joining of the two seas. En route back to the Masseria we visit Otranto, the beautiful ancient portal town of Greek origin that has been the bridge between East and West. The old town is an open book on the troubled times of the Middle Ages. 

Day 8:
After breakfast we transfer you to Bari airport for your journey back home. 


  • Flights

  • Lunches, dinners and beverages

  • Single room supplement of £227

  • Transfers from and to airport other than Bari

  • Bike hire: from £145 (includes cycle computer, repair kit, pump, lock)

  • Gratuities and items of a personal nature

  • Bicycle case storage: £55

  • Cooking class (arranged upon request)

For groups of 6 or more:
All our cycling itineraries can be customized to your specific tastes and requirements.