Puglia: The Heel of the Boot

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From the “Sassi of Matera” in Basilicata, You’ll cycle towards the Apulian land.

This adventure starts with the crossing of the Murgia plateau. You will also ride in the Itria valley, characterized by the flourishing vegetation in the midst of olive orchards. These vast orchards are cultivated on numerous local farms called Masserie; small, typical stone fortresses. Puglias coasts are marked by long, sandy beaches, dunes and protected natural reserves. In this region you can find trace of old Messapi civilizations, rock settlements, castles and not-to-be-missed trullos made with dry stone techniques.
Sun, Sea and Wind; On the last days of this tour heading south towards the Salento, Nature is the first striking theme as the land stretches in balance between two seas. The Salento cities and inland towns express the unique Lecce Baroque style with Messapi and Salento Grecìa influence, which can still be seen. Its language, songs and feasts still reflect the culture of Magna Graecia. The typical local music called Pizzica, will introduce you into the local life of the Dolcevita.


  • Journey through the heart of the boot of Italy, to the sensational baroque town of Lecce
  • Cycling from Sassi di Matera to Trulli di Alberobello, both UNESCO Heritage Sites
  • Overnight in 4 Superior hotels and Masseria resorts
  • Cycling along one of Italy’s most stunning coastal road
  • Taste local delicacies like Orecchiette pasta


DAY 1– Welcome to Basilicata MATERA
Independent arrival to Matera and get settled in at your hotel. Tour Briefing and bicycle delivery/fitting.
Upon request: Guided walking visit of the Sassi (ancient Matera district) and the Park of Rupestrian Churches. We suggest a dinner (on your own) in a typical Sassi restaurant, carved into the Rocks.
Overnight in Matera.

DAY 2– Alberobello and Trulli
Distance: Km 69 / 43 mi
Difficulty: Easy to Moderate route on stretches false flats and rolling hills.
Bike ride from Matera to Alberobello – You will pass through the small villages of Gioia del Colle and Noci on your way to Alberobello; the capital town of Trulloes and a UNESCO’s world heritage site.
Accommodation: in a Trullo house or a restored farmhouse.
Overnight in Alberobello

DAY 3 – Ostuni, the White Town
Distance: 45 km / 28 mi
Difficulty: Easy to Moderate.
Crossing the Itria Valley, with stops in the characteristic towns of Locorotondo and Cisternino, you will reach the city of Ostuni which is reputed an architectural jewel. Ostuni is commonly referred to as “The White Town” for its typically white-painted walls and unique architecture.
Overnight in Ostuni

DAY 4 – Castles and Farmhouses
Distance: 55 km / 34 mi
Difficulty: Easy to Moderate.
Cycling south through the quiet countryside to the charming town of Francavilla, Fontana and onto your destination of Oria; famous for its 13’th century Castle and delightful historic center. Your accomodation will be in a typical Apulian Masseria (converted farmhouse) for the night.
Overnight in Manduria

DAY 5 – Gallipoli and the Ionian Coast
Distance: 60 km / 37.5 mi
Difficulty: Easy to Moderate.
Today, our chosen route will pass through Porto Selvaggio and skirt the Ionian coast to reach Gallipoli; derived from the Greek word Kalépolis meaning “beautiful city.” Along this route you may want a picnic lunch on a sandy beach and try for a swim if the weather permits.
Overnight in Gallipoli

DAY 6 – Otranto, the Far East
Distance: 71 km / 44 mi
Difficulty: Moderate to Challenging.
Cycling to Otranto, todays route will take you to the wildest and most eastern rocky coast of Southern Italy. Here, even the sun and the atmosphere seems unique, where Turkish and Greeks landed centuries ago. Otranto has a wonderful center with its city walls and castle. The Romanesque Cathedral holds a mysterious mosaic masterpiece not to be missed.
Overnight in Otranto

DAY 7 – Lecce, the Baroque gem
Distance: 45 km / 28 mi
Difficulty: Easy to Moderate.
Last stage of your journey will take you to the town of Lecce, filled with wonderful façade of Baroque buildings and churches. Taste a puccia (local bread filled with salami or vegetables) or a pasticciotto (delicious local pastry), and enjoy shopping and walking in the city center.
Overnight in Lecce

DAY 8 – End of Tour after breakfast
Departure: Train and buses available to reach Bari, where you can take fast train connections to other towns or fly out from the airport.

Cost: 1490 € p/person

Price: Based on double room
Single Supplement:  360 €
Tour name: Puglia, the Heel of the Boot
Tour type:  Self Guided bike tour


  • Seven nights in excellent four & three-star superior hotels
  • Seven breakfasts
  • Bike fitting in Mater on arrival day
  • Route notes, maps, metrics and city maps
  • Sightseeing, restaurant and shopping suggestions
  • All Baggage transfers
  • Pick-up of bikes and gear in Lecce
  • Keepsake BTS water bottle
  • Sales taxes

Not included:

1) Bike Rental per entire tour:
Hybrid bike € 140
Race bike (full carbon) € 210
E-Bike € 210
2) City Tax each town charges a tax per each day between € 0,70 to 4,00.

Total distance: 160 to 190 miles
Daily Mileage: 35-40  mi on rolling hilly terrain with some climbs. Additional mileage available upon request.
Duration: 8 days / 7 nights





Day 1: Palazzo Gattini, Matera

The Palazzo, after its ancient and noble scenario, has been renewed and has opened its doors to the town as well as to travelers. Suffused and gentle lighting invites you to slow down the pace, and gives you the pleasant relax and creates warming moments. The furnishings have turned out to be the result of the best local craftsmen’s creations, who helped to enrich and embellish the palace.


Day 2: Corte dell’Astore, Alberobello

La Corte dell’Astore reflects a new idea of hospitality, that makes the guest the main character of a fairy tale with a happy ending and whose story unfolds in a mixture of creativity, passion and emotion. The story begins from the heart of the creator of La Corte Dell’Astore. He is a master of stonework, loves beauty, is deeply rooted in his place of origin, Alberobello, and is fond of falconry.


Day 3: Ostuni Palace, Ostuni

Recently constructed, the Hotel Ostuni Palace boasts a strategic position from which you can admire the charm of the charming town lying on a dense hillside of whitewashed houses and alleys with fascinating glimpses. In the background, you can not miss the blue of the crystal clear sea that you can see through the extraordinary expanse of olive trees surrounding the city.


Day 4: Masseria Bagnara, Lizzano

An oasis of peace and tranquillity where the warm apulian sun gently caresses this ancient country house white walls. The renovation, made according to tradition, added features and details thus reinventing the fascinating personality and history of Masseria Bagnara. A scenery that will let the Guest feel pampered and relaxed right from his arrival. Surrounded by a beautiful countryside and just a few steps away from the cristal clear Mediterranean Sea, you will enjoy a stay focused around your wellness, right in the middle of Apulia.


Day 5: Palazzo del Corso, Gallipoli 

The five star luxury Hotel Palazzo Del Corso is an elegantBoutique Hotel situated in the main street of Gallipoli, just a few steps awayfrom the old town centre and a few kilometers away from historical sites, cultural places and wonderful landscapes like Lecce, Otranto and Santa Maria di Leuca. Born from the renovation of two ancient buildings of XIX century, the Hotel reflects the love for luxury and the attention to details. It has got a panoramic terrace with a hydro massage-pool where you can spend relaxing moments


Day 6: Masseria Montelauro, Otranto

Masseria Montelauro is an ancient residence of 1878. Immersed in the light and colors of Otranto’s countryside, 2 km from the sea and the town center, the Masseria has been restored in full respect of its original rural nature, including drywall and secular olive trees. Guests of the Masseria will be able to breathe the warm atmosphere of Salento tasting in the restaurant typical dishes of the otrantina tradition


Day 7: Suite Hotel Santa Chiara, Lecce

Suite Santa Chiara is a 4-star boutique hotel located in Lecce’s historical centre, 100 metres from the cathedral. The roof garden on the 4th floor has a bar, outdoor seating and views of the historic centre.Rooms are very elegant and nicely decorated with soothing tones.  As you will know, the Suite Hotel Santa Chiara has 21 furnished apartments with a refined elegance that overlook the most important corners of the city of art.


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