Sicily, Walking & Cycling Holidays in Italy
8 days / 7 nights
8 days / 7 nights
From Matera's Ancient Caves to Alberobello's Trulli.
Cycle through one of Southern Italy's most fascinating landscapes, where ancient cave dwellings, dramatic limestone ravines, centuries-old olive groves and whitewashed villages create a journey unlike any other. This 8-day self-guided cycling holiday connects two extraordinary UNESCO World Heritage sites—Matera and Alberobello—before reaching the sun-drenched shores of the Ionian Sea.
Rated Easy to Moderate, the route covers approximately 280km, combining quiet country roads with gentle climbs and exhilarating descents through the rugged countryside of Basilicata and Apulia. Along the way, you'll discover a landscape shaped by generations of farming, ancient civilisations and deeply rooted traditions, with wonderfully characterful places to stay—from a cave hotel in Matera to an authentic trullo in Alberobello and welcoming countryside agriturismi.
Tour Type
Self Guided
Duration
8 days / 7 nights
Activity Days
6 days
Level
Easy to Moderate
Avg. Daily Distance
70 km
Most Enjoyable Months
mar, apr, may, jun, sep, oct
Arrival/Departure Town
Matera / Matera
Enjoy an included 2-hour guided walking tour through the ancient cave districts, rock churches, and subterranean cellars.
Sleep inside an authentic 1600s trullo in the heart of the world capital of trulli houses.
Cycle through two of Italy's most beautiful whitewashed hill towns and sample local DOC white wine.
Climb to the magnificent Benedictine Abbey overlooking the Bradano Valley.
Walk into the Gravina canyon and discover the ancient rupestrian village and caves of Cristo La Selva.
Day
Route
Meals
Distance
Elevation
Time
Activity
Day 1
Arrival in Matera
B
Check In
Day 2
Matera to Alberobello
B
69 km | 43 mi
Cycling
Day 3
Alberobello Vineyard & Cave Loops
B
45 km | 28 mi
Cycling
Day 4
Alberobello to Castellaneta Marina
B
70 km | 43 mi
Cycling
Day 5
The Bradano Valley & Montescaglioso
B
55 km | 34 mi
Cycling
Day 6
Rest Day or The Ancient Via Appia
B
35 km | 22 mi
Rest Day/Cycling
Day 7
Montescalgioso to Matera
B
25 km | 16 mi
Cycling
Day 8
Departure from Matera
B
Check Out
Day 1
Arrival in Matera
Meals
B
Distance
Elevation
Time
Activity
Check In
Day 2
Matera to Alberobello
Meals
B
Distance
69 km | 43 mi
Elevation
Time
Activity
Cycling
Day 3
Alberobello Vineyard & Cave Loops
Meals
B
Distance
45 km | 28 mi
Elevation
Time
Activity
Cycling
Day 4
Alberobello to Castellaneta Marina
Meals
B
Distance
70 km | 43 mi
Elevation
Time
Activity
Cycling
Day 5
The Bradano Valley & Montescaglioso
Meals
B
Distance
55 km | 34 mi
Elevation
Time
Activity
Cycling
Day 6
Rest Day or The Ancient Via Appia
Meals
B
Distance
35 km | 22 mi
Elevation
Time
Activity
Rest Day/Cycling
Day 7
Montescalgioso to Matera
Meals
B
Distance
25 km | 16 mi
Elevation
Time
Activity
Cycling
Day 8
Departure from Matera
Meals
B
Distance
Elevation
Time
Activity
Check Out
Day 1
The Ancient City of Stone.
Arrive in Matera, one of Southern Italy's most extraordinary and atmospheric cities, and settle into your hotel. This afternoon, join an included two-hour guided walking tour through the remarkable Sassi di Matera, a UNESCO World Heritage Site since 1993.
Wander through a maze of narrow lanes, stone stairways and terraces carved into the ancient ravine, discovering rock-hewn churches, cave dwellings, ancient cellars and homes carved directly into the limestone. Some of these remarkable spaces were inhabited continuously from medieval times until as recently as the 20th century.
This evening, experience Matera's unique atmosphere over dinner in a traditional cave restaurant, where the setting is every bit as memorable as the local cuisine.
Overnight: Matera
Day 2
Journey to the Capital of Trulli.
Terrain: Easy to Moderate.
Receive your bike handover and tour briefing before setting off for Apulia. Ride through the picturesque agricultural villages of Gioia del Colle and Noci before arriving in Alberobello, the UNESCO-listed capital of trulli. Check into your unique accommodation: an authentic historical trullo dating back to the 1600s.
Overnight: Alberobello
Day 3
The Whitewashed Itria Valley.
Terrain: Easy to Moderate.
After your bike handover and tour briefing, leave Matera behind and begin your journey into Apulia. Ride through the peaceful countryside and agricultural landscapes around Gioia del Colle and Noci, where vineyards, olive groves and traditional farmsteads create a quintessential southern Italian backdrop.
Continue towards Alberobello, the enchanting UNESCO World Heritage town famous for its extraordinary collection of trulli—whitewashed limestone dwellings topped with distinctive conical roofs.
Your accommodation tonight is part of the experience itself: settle into an authentic historic trullo dating from the 17th century, giving you the rare opportunity to spend the night inside one of Apulia's most iconic architectural traditions.
Overnight: Alberobello
Day 4
The Land of the Ravines.
Terrain: Easy to Moderate.
Leave the trulli of Alberobello behind and cycle south into the province of Taranto, following quiet country roads through a landscape of vineyards, olive groves and fertile farmland.
As you approach Mottola and Palagianello, the scenery becomes increasingly dramatic as you enter the Land of the Ravines. Here, the limestone plateau is carved by deep, spectacular gorges, with sheer canyon walls plunging more than 100 metres into the valleys below. Keep an eye out for ancient cave settlements and rock-hewn churches hidden among the cliffs.
Continue towards the Ionian coast, where you can finish the day with the sea breeze at Castellaneta Marina. Alternatively, your overnight stay may be at a peaceful agriturismo along the Bradano River, surrounded by the countryside.
Overnight: Castellaneta Marina or Bradano River
Day 5
Abbeys and Farm Estates.
Terrain: Easy to Moderate.
Follow the winding Bradano River through fertile countryside, where orange groves, vineyards and fields create a peaceful rural landscape. The route gradually climbs towards Montescalgioso, a historic hilltop town overlooking the surrounding valleys.
Take time to explore the town's impressive Benedictine Abbey of San Michele Arcangelo, one of Basilicata's most important monastic complexes, before enjoying the descent back into the valley.
Tonight, experience the authentic countryside of Southern Italy with a stay at a working agriturismo, set among vegetable fields and farmland. Relax by the swimming pool and savour the slower pace of rural life.
Overnight: Agriturismo near Montescalgioso
Day 6
Roman Roads and Valley Views.
Terrain: Easy to Moderate.
Today is yours to enjoy at your own pace. Relax by the pool at your agriturismo, soak up the peaceful countryside, or set out on a scenic loop ride along one of Italy's most historic roads.
The cycling option follows sections of the ancient Via Appia, the celebrated Roman road that once connected Rome with the south of Italy. Continue to the charming hilltop village of Miglionico, where panoramic views stretch across the surrounding valleys and rugged Basilicata landscape.
After exploring the village, return by bike to your agriturismo and enjoy another relaxing evening in the countryside.
Overnight: Agriturismo near Montescalgioso
Day 7
Park of the Rock Churches.
Terrain: Easy to Moderate.
Set out towards Matera, cycling along the edge of the extraordinary Park of the Rock Churches, where rugged limestone landscapes, deep ravines and ancient cave settlements define the countryside.
After approximately 12 km, leave your bikes behind and continue on foot into the spectacular Gravina canyon. Follow the trail through this dramatic landscape to Cristo La Selva, an ancient rupestrian settlement hidden among the caves and cliffs. This remarkable site offers a fascinating glimpse into the region's centuries-old tradition of living, worshipping and farming within the rock.
Return to your bikes and continue towards Matera, arriving in time to enjoy a free afternoon. Explore more of the Sassi, relax at your hotel, or simply wander through the atmospheric streets of this extraordinary city.
Overnight: Matera
Day 8
Your cycling adventure through Basilicata and Apulia comes to an end after breakfast in Matera.
If you have time, we recommend extending your stay to explore more of Matera's remarkable Sassi, cave churches and historic streets before continuing your journey.
Tour Ends: Matera
7 nights in double/twin rooms including cave hotels, authentic trulli, and farm stays (agriturismi).
Breakfast daily.
2-hour guided walking tour of the Sassi di Matera.
Reliable luggage transfers between all accommodations.
Detailed road book and technical/emergency hotline assistance. (Guided group option includes a cycling guide, daily breakfasts & dinners, and Bari airport transfers).
Medical/luggage insurance and transportation to/from Matera.
Lunches and drinks during dinners.
Entrance fees to churches, caves, and museums.
Tips, personal extras, and local city hotel taxes (approx. €2–4 per person/night paid directly to hotels).
Minivan support available on demand for an extra charge.
How difficult is cycling in Basilicata and Apulia?
This tour is graded as Easy to Moderate. The terrain is characterized by rolling hills, with daily cycling distances ranging between 25km and 70km. While there are gentle ascents leading up to hill towns like Montescalgioso and Locorotondo, the roads are mostly deserted and rural, offering a very comfortable pace.
What are the Sassi di Matera?
The Sassi di Matera are ancient cave dwellings carved directly into the limestone canyons of Basilicata. Inhabited since the Paleolithic era, they form one of the oldest continuously inhabited settlements in the world and were recognized as a UNESCO World Heritage site in 1993. Your tour includes a 2-hour guided walking tour to explore these subterranean caves and urban structures.
What kind of accommodations will I stay in on this tour?
This tour emphasizes unique, authentic local stays. Depending on the stage, you will stay in historical cave hotels in Matera, sleep inside an authentic 17th-century drystone trullo in Alberobello, and relax at working farm estates (agriturismi) complete with swimming pools.
When is the best time of year to cycle this route?
The self-guided tour runs daily through March, April, May, June, September, and October. Spring and autumn offer ideal, comfortable cycling weather. July and August departures are only available on request, as mid-summer temperatures in Southern Italy are very hot and busy.
How do I get to Matera to start the cycle tour?
Matera is easily reached from Bari International Airport (BRI) , located approximately 60km away. Direct airport shuttle buses, private transfers, and regional train connections connect Bari Airport and Bari Central Station to Matera.
What is the "Land of the Ravines" (Terra delle Gravine)?
Encountered on Day 4 near Mottola and Palagianello, the Terra delle Gravine is a spectacular natural regional park defined by massive limestone canyons formed by river erosion. These precipices—often reaching depths of over 100 meters—resemble North American canyons and served as natural defensive shelters and cave villages during medieval times.
What is the Park of Rock Churches in Matera?
Located on Day 7 of your itinerary, the Parco delle Chiese Rupestri (Park of the Murgia Materana) encompasses over 150 ancient rock-carved churches and monastic hermitages. Carved into the canyon walls by Byzantine and Benedictine monks between the 8th and 13th centuries, many of these cave sanctuaries feature ancient fresco paintings preserved on their stone walls.
What makes Locorotondo one of Italy's most beautiful villages?
Located in the Itria Valley, Locorotondo gets its name from its circular, hilltop town layout ("locus rotundus"). Voted one of the "Borghi più belli d'Italia" (Most Beautiful Villages of Italy), it is renowned for its gleaming whitewashed houses with pointed gable roofs (cummerse), flower-filled balconies, and delicate DOC white wine.
What are the Castellana Caves (Grotte di Castellana) featured on Day 3?
If you choose the optional 40 km loop ride on Day 3, you will have the opportunity to visit the spectacular Castellana Caves. This massive underground karst cave system stretches for approximately 3 kilometers and plunges to depths of over 120 meters. It is widely considered one of Italy's most extraordinary natural wonders, featuring towering stalactites, stalagmites, and the legendary Grotta Bianca (White Cave), which is famously celebrated as one of the most resplendent caves in the world due to its striking alabaster-like whiteness.
What is the historical significance of Miglionico and its castle?
On Day 6, your ride along the ancient Roman Via Appia takes you to the charming hilltop village of Miglionico. The town is dominated by the Castello del Malconsiglio (Castle of Bad Counsel), an imposing 8th-9th-century fortress flanked by towers that offers sweeping views over the Bradano Valley. The castle earned its infamous name because it was the site of the dramatic "Conspiracy of the Barons" in 1485, where southern Italian nobles plotted against King Ferdinand I of Naples.
What is the architectural difference between Matera's Sassi and Alberobello's Trulli?
This cycle tour uniquely links two entirely different, UNESCO-recognized ancient building techniques.
The Sassi di Matera (Basilicata) are ancient subterranean cave dwellings, cellars, and rupestrian churches carved directly into the steep limestone faces of a canyon.
The Trulli of Alberobello (Apulia) are above-ground, whitewashed limestone dwellings featuring iconic, cone-shaped roofs. They are remarkable examples of a prehistoric drywall (mortarless) construction technique that remains in use across the Itria Valley today.
What will I see in the Bradano Valley?
You will cycle through the Bradano Valley on Days 5 and 6 of your itinerary as you loop back into the Basilicata region. Following the winding path of the Bradano River, this tranquil, rolling agricultural area is awash with color and features ancient olive trees, fragrant orange groves, sweeping vineyards, and traditional farmhouses. The valley is also home to the natural oasis of San Giuliano Lake and is majestically overlooked by the Benedictine Abbey of Montescalgioso.
30+ Years
2 star
AUDs quote
GBPs quote
Cycling
Top Choice
Self Guided
Walking & Cycling Holidays in Italy | Tuscany
Moderate to Challenging
Cycling
Popular
Top Choice
Self Guided
Walking & Cycling Holidays in Italy | Tuscany
Moderate
Cycling
Popular
Top Choice
Self Guided
Walking & Cycling Holidays in Italy | Puglia
Easy to Moderate
Cycling
Popular
Top Choice
Self Guided
Walking & Cycling Holidays in Italy | Tuscany
Moderate