Puglia Cycling | The Heel of the Boot | Luxury Self guided

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Puglia Cycling Tour on Luxury Accommodations: Pedalling from the “Sassi of Matera” in Basilicata, You’ll cycle towards the Apulian land and arrive at the Heel of the Italian boot.

This Luxury bicycle tour  in Southern Italy will be an adventure hard to forget: superior food, outstanding wines and beautiful roads, surfing between history and gorgeous coastal tracks.

This Puglia Cycling tour 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 the 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 kitchen still reflect the culture of Magna Graecia.

The typical local music called Pizzica, will introduce you into the local life of the Dolcevita.

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Tour Details
Tour name Puglia. The Heel of the Boot
Type of tour Self guided, you can start any day of the week
Duration 8 nights, 9 days
Period  From March to November
Level Leisure, additional mileage available
Total Distance 345km / 213mi
Daily mileage 45 to 70km / 28 to 43mi
Start Matera
End Lecce
Suggested Airports In: Bari. Out: Brindisi or Bari


  • 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
Not Included
Optional Services
  • Eight nights in excellent 4 & 3 star superior hotels and Masseria
  • Eight breakfasts
  • Bike fitting in Matera on arrival day
  • Private Event on RWGPS APP, easy to follow on your own mobile
  • Sightseeing, restaurant and shopping suggestions
  • All Baggage transfers
  • Pick-up of bikes and gear in Lecce
  • Keepsake BTS water bottle
  • Sales taxes
  • City Tax; each village charge a tax per each day between euro 0,70 to 2,50
  • Bike Rental
  • Pre/Post Additional Nights
  • Transfers to/from other destinations on the Island
  • Cooking lessons
  • Wine tasting
  • Dinners and activities booking
  • Room upgrade

Day 1Benvenuti to Matera, Basilicata. Meet & Greet

Independent arrival in Matera and get settled in at your hotel. Meet with Bike Tour representative for briefing and delivery of bicycles. Upon request: guided walking visit of the Sassi (ancient Matera districts) and the Park of Rupestrian Churches can be arranged. We suggest a dinner (on your own) in a typical Sassi restaurant carved out into the Rocks.
Lodging at Palazzo Gattini in Matera
Meals included: Breakfast

Day 2 Matera to Alberobello and Trulli. 69 Km / 43 mi, rolling hills

For your first ride, you will pass through the small villages of Gioia del Colle and Noci and on to Alberobello, the capital town of Trulloes and a UNESCO’s world heritage site. Accommodation in a Trullo house or a restored farmhouse.
Difficulty: Hilly route on stretches that are almost flat with brief climbs.
Lodging: at Trulli Holiday in Alberobello
Meals included: Breakfast

Day 3Alberobello to Ostuni, the white town. 45 km / 28 mi, rolling hills

Crossing the Itria Valley, with stops in the characteristic Locorotondo and Cisternino, you will reach Ostuni, which is reputed an architectural jewel, and is commonly referred to as “the White Town” for its white walls and its typically white-painted architecture.
Lodging: at hotel Ostuni Palace**** in Ostuni
Meals included: Breakfast

Day 4 Ostuni to Manduria, Castles & Masserie. 55 km / 34 mi, downhill and flat

Cycling south through the quiet country lanes to the charming town of Francavilla Fontana and on to Oria, famous for its 13th Century’s Castle and delightful historic center. You will reach a Masseria, a typical Apulian converted farmhouse, your accommodation for the night.
Lodging at Vinilia Resort, Manduria
Meals included: Breakfast

Day 5Manduria to Gallipoli & Ionian Coast. 76 km / 47,5 mi, rolling hills and flat

Today your route will pass through Porto Selvaggio and skirt the Ionian coast to reach Gallipoli, derived from the Greek word kalépolis meaning “beautiful city.” Have a picnic on a sandy beach and try to swim if the weather is nice.
Lodging: at the charming Hotel Palazzo del Corso ***** in Gallipoli
Meals included: Breakfast

Day 6 Gallipoli to Santa Maria di Leuca, the heel. 52 km / 32 mi, mostly flat

You have the possibility to add one day (or more) to your fantastic tour in Puglia; one of the most requested is the ride to Santa Maria di Leuca where you can admire the cliffs along the scenic Southern Coast. In this case the tour will finish always in Lecce, because the additional day is between Day 6 and 7.
Ask for a quote.
Lodging: at Montirò Hotel in Leuca
Meals included: Breakfast

Day 7Santa Maria di Leuca to Otranto & the Far East. 61 km / 40 mi, rolling his

Cycling to Otranto, the route will take you to the wildest and eastern rocky coast of Southern Italy. The sun and the atmosphere is unique in a place where Turkish and Greeks landed centuries ago. Otranto has a wonderful center with walls and a castle. A masterpiece is the mysterious mosaic, in the Romanesque Cathedral.
Lodging: at Relais Valle dell’Idro in Otranto
Meals included: Breakfast

Day 8Otranto to Lecce, the Baroque gem. 45 km / 28 mi, rolling ills

Last stage will take you to Lecce, the Baroque town with wonderful façade of buildings and churches. Taste a puccia (local bread filled with salami or vegetables) or a pasticciotto (delicious pastry), and enjoy shopping and walking in the city center.
Lodging: at hotel Palazzo dei Dondoli in Lecce
Meals included: Breakfast

Day 9Arrivederci! Good bye!

Departure: train and bus available to reach Bari, Brindisi Airports or where you can take fast train to other towns.
Meals included: Breakfast


Self Guided
Tour Price: 2210€

Price based on double accommodation, it can change according to the period.

Make it custom: contact us for a quote!

Single occupancy: 780 €

Private & Custom departures at any time

Road bike for rental


Carbon frames with Ultegra 11 speed; compact groupset.



Discover the Sardinian Strade Bianche on Gravel bikes.

Electric bike for rental


The hills won’t be so hard with our new Scott E-Bikes.

Touring Hybrid bike for rental


Hybrid-Touring bikes very light to face the Italian Hills.

Lodging Sample
Palazzo Gattini Matera self guided cycling
Day 1 – Palazzo Gattini Luxury Hotel, Matera

alazzo Gattini Luxury Hotel is located in the Matera Sassi area, a UNESCO World Heritage Site. It offers free Wi-Fi, unique rooms with stone bathrooms, and free access to the property’s spa.

Day 2 – Le Alcove, Alberobello

Experience an unusual mix of modern comforts and ancient stone dwellings when you stay at Le Alcove-Luxury Hotel nei Trulli; a series of traditional Trulli huts in the heart of Alberobello.

Ostuni Palace superior bike tour
Day 3 – Ostuni Palace Hotel, Ostuni

With its impressive façade, Ostuni Palace fits in perfectly in the White City of Ostuni. It offers a spa, an elegant piano bar, and an Italian restaurant. All rooms are air-conditioned and have free wired internet.

Manduria by bike vinilia resort
Day 4 – Vinilia Resort, Manduria

Vinilia has started in the savage land, just outside Salento, Apulia. Here, an antique Castle is transformed into a unique experience of style and warmth, because the beauty is in the eyes of who sees and in the heart of who appreciates it.

Palazzo Gattini Matera
Day 5 – Palazzo del Corso Luxury Hotel, Gallipoli

The five star luxury Hotel Palazzo Del Corso is an elegant Boutique Hotel situated in the main street of Gallipoli, just a few steps away from the old town centre and a few kilometres away from historical and cultural sites

Leuca cycling tour puglia
Day 6 – Montirò Hotel, Leuca 

With a peaceful location in the beautiful Salento area, Montiro’ Hotel features a vast garden with a swimming pool and olive trees.

bike tour puglia palazzo de mori
Day 7 – Palazzo De Mori, Otranto

Facing the sea in the restricted-traffic area of Otranto’s historic center, this elegant B&B offers air-conditioned rooms with free Wi-Fi. Breakfast includes homemade cakes. The property is 656 feet from Otranto’s Cathedral, and a 5-minute walk from the beach.

Puglia Bike Tour
Day 8 – Patria Palace, Lecce

Patria Palace Lecce provides first-class luxury and service in the heart of Lecce, next to the Basilica of Santa Croce and a few steps from the Roman amphitheater.