Sassi and Trulli 8 Days Cycling Tour

After staying in the Sassi di Matera, the ancient cave dwellings carved into the rock in one of Italy’s most iconic UNESCO World Heritage Sites, you will continue toward the enchanting Itria Valley. This karstic landscape—also known as the Valley of the Trulli—is famous for its unique trullo houses, traditional conical stone dwellings found only in Apulia (Puglia).

On your way back to Basilicata, you will pass through the charming hilltop town of Montescaglioso, renowned for its impressive Benedictine Abbey of San Michele Arcangelo, historic palaces, and panoramas over the surrounding countryside. A short ride further brings you to Miglionico, a medieval village dominated by Castello del Malconsiglio, a fortress steeped in history and legends that offers breathtaking views of the Bradano Valley.

From here, you will cycle through rolling hills bursting with colors, surrounded by ancient olive groves, vineyards, and traditional masserie (farmhouses).

The region’s rich local culture, authentic traditions, and delicious Southern Italian cuisine will immerse you in the unforgettable atmosphere of this captivating corner of Basilicata and Apulia, making your journey truly memorable.

Highlights

The Sassi of Matera
The Trulloes and the Itria Valley
The Land of Ravines
The Bradano Valley

Itinerary

Day 1 – Matera

Arrival in Matera and transfer to your hotel.
Suggested (not included): guided tour around the Sassi – a UNESCO world heritage site since 1993 – with its small streets and squares, caves, rock churches and cellars. Two districts built from the Medieval age through to the last century. We suggest you have dinner at one of the Sassi’s typical restaurants. Overnight stay.

Day 2 – from Matera to Alberobello

Distribution of bicycles, briefing and departure for Alberobello. 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 world heritage site. Accommodation in the historical centre in a trullo dating from 1600. Overnight stay.
Length: 69 km
Grade: Easy to Moderate

Day 3 – Alberobello Loop

A day cycling among trulli houses, dry stone walls, vineyards, vegetable gardens and cattle farms. You will visit Locorotondo, Cisternino and Martina Franca.
A picnic under an oak tree, an aperitif with a view of the valley, a wine tasting in a cellar, will make your ride a perfect experience.
Length: Approx. 50 km
Grade: Easy

Day 4 – The Land of Ravines

Heading south into the Taranto province, you will pedal through deserted roads and vineyards. You will cross the Land of the Ravines and the villages of Mottola and Palagianello. The Ravines are deep precipices, often more than 100 metres deep, similar to canyons. Overnight stay in a farm not far from the Bradano River.
Length: Approx. 65 km
Grade: Easy to Moderate

Day 5 – greek ruins and ionian sea

Start your ride through quiet country roads lined with citrus groves and ancient olive trees as you head toward the majestic Tavole Palatine, the well-preserved Doric temple dedicated to Hera, a striking reminder of Magna Graecia. After a short visit, continue cycling toward the wide sandy beaches of Metaponto, where the turquoise Ionian Sea offers a refreshing break.
Enjoy the coastal atmosphere before turning inland along gentle farmland landscapes and rural tracks, making your way back to your hotel for a relaxing end to your ride.

Length: Approx. 37 km
Grade: Easy

Day 6 – the Bradano Valley

Today you will continue pedaling along the Bradano River through vineyards and orange trees. After a light ascent on the Montescaglioso hill (a visit to the Benedictine Abbey is a must), back to the valley you will reach Miglionico, a medieval hilltop village famed for its historic Malconsiglio Castle.
Length: Approx. 49 km
Grade: Easy to Moderate

Day 7 – Back to Matera

From Miglionico, your ride begins with gentle hills leading toward the medieval village of Grottole, surrounded by forests, clay hills, and quiet rural landscapes. Continue cycling along panoramic country roads until you reach the tranquil Lake San Giuliano, a protected natural oasis where reed beds, birds, and shimmering water create a peaceful backdrop for your ride.
Back in Matera, enjoy a free afternoon to visit museums, explore the winding alleys of the Sassi, and end your day with a memorable dinner in a traditional cave restaurant.
Length: Approx. 54 km
Grade: Moderate

Day 8 – End of tour

Breakfast and end of tour.