This 8-day cycling journey through Puglia is a slow ride through one of southern Italy’s most delicious regions. Starting in Matera’s surreal cave city, we pedal quiet backroads through olive groves, vineyards, and whitewashed villages as we cross the Valle d’Itria and the Salento peninsula. Along the way, trulli houses, hill towns, and endless countryside set the scene, while stops for olive oil, local wine, and long Italian lunches keep the energy high. We finish on the Adriatic in Otranto, with a week of scenic riding, incredible food, and beautiful masserias behind us.
We arrive in Bari and transfer to Matera, one of southern Italy’s most fascinating historic cities. After settling into our boutique hotel in the old town, we head out on a guided walk through the UNESCO-listed Sassi districts, where cave dwellings carved into limestone create one of Italy’s most unique landscapes. In the evening, we gather for a welcome dinner and our first taste of Lucanian cuisine.
Accommodation: Boutique hotel in Matera
Meals: Dinner
After a bike fitting and technical briefing, we roll out for our first ride across the Murgia plateau. Quiet countryside roads lead us toward the historic town of Altamura, famous for its traditional bread. Later in the day, we dive deeper into local flavors with either a bread-making workshop dedicated to Altamura bread or a guided wine tasting with a local sommelier.
Accommodation: Boutique hotel in Matera
Meals: Breakfast, dinner
Cycling: 58 km (36 mi), rolling terrain
Elevation gain: 450 m (1,476 ft)
Today we leave Basilicata and ride into Puglia along quiet rural roads surrounded by farmland and olive groves. As we enter the Valle d’Itria, the scenery shifts and the iconic trulli houses begin to appear along the route. Our destination is Alberobello, the UNESCO-listed town famous for its cone-roofed stone houses, where we spend the night in a traditional trullo-style property or countryside masseria.
Accommodation: Trullo-style hotel or countryside masseria in Alberobello / Valle d’Itria
Meals: Breakfast, dinner
Cycling: 69 km (43 mi), rolling terrain
Elevation gain: 520 m (1,706 ft)
Today’s ride explores the heart of the Valle d’Itria, a region known for its vineyards, olive groves, and dry-stone walls dividing the countryside. Quiet backroads take us through small villages and rolling landscapes before we approach Ostuni, the famous White City overlooking the Adriatic coast. Along the way, we stop for an olive oil tasting before returning to our countryside masseria.
Accommodation: Countryside masseria in Valle d’Itria
Meals: Breakfast, dinner
Cycling: 50 km (31 mi), gentle rolling terrain with short climbs
Elevation gain: 530 m (1,739 ft)
We continue south toward the Salento region, cycling through quiet countryside and small villages as the terrain becomes flatter. Our destination is Manduria, one of the historic homes of Primitivo wine. After settling into a beautiful wine resort, we enjoy a tasting of local wines before dinner.
Accommodation: Vinilia Wine Resort, Manduria
Meals: Breakfast, dinner
Cycling: 60 km (37 mi), mostly flat terrain
Elevation gain: 300 m (984 ft)
We follow the Ionian coast through the protected natural park of Porto Selvaggio before rolling into Gallipoli—derived from the Greek kalépolis, meaning “beautiful city.” The ride is relaxed and scenic, with the sea never far away. We stop for a beach picnic and, if the weather plays along, a swim before arriving in town for dinner.
Accommodation: Relais Corte Palmieri
Meals: Breakfast, dinner
Cycling: 55 km (34 mi), flat terrain
Elevation gain: 180 m (591 ft)
Today we cross the Salento peninsula, linking the Ionian and Adriatic coasts. Quiet inland roads lead us through villages and Mediterranean landscapes before we reach Otranto, one of Puglia’s most beautiful seaside towns. After exploring the town and visiting the cathedral, we celebrate the journey together with a farewell dinner.
Accommodation: Masseria dei Monaci, Otranto
Meals: Breakfast, dinner
Cycling: 72 km (45 mi), rolling terrain
Elevation gain: 490 m (1,607 ft)
After breakfast, the trip concludes. Transfers are available to Bari or Brindisi airports.
Meals: Breakfast
Included:
Add-ons (pricing shown at checkout):
Not included:
To join this Puglia cycling holiday, good fitness is recommended. Expect cycling up to 72 km (45 mi) & around 4–5 hours per day, with up to 530 m (1,739 ft) of elevation gain. The terrain is mostly rolling with some flatter coastal sections, and rides take place on quiet countryside roads.
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Here’s a list of the equipment you need to bring:
Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.
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Group sizes and pricing
A Puglia cycling holiday can be arranged for larger groups. Contact us to make arrangements.
Min. age requirements
If your group has participants under the age of 18, contact us prior to booking to make arrangements.
The price for this Puglia cycling holiday is based on twin-share rooms, but a single occupancy room can be arranged at an additional fee. You can add it to your booking at checkout.
The starting point of your Puglia cycling holiday is Matera. To get there, most people fly into Bari Airport (BRI). From there, you can take a shuttle service, public transport, taxi, or rent a car to reach Matera.
You will meet your guide on Day 1 at your hotel in Matera.
We highly recommend that you cover all your bases with insurance. To make your booking and traveling experience as carefree as possible, you’ll be offered to simply insure your trip with Redpoint at checkout.
Redpoint—the official 57hours insurance partner—tailors protection packages for adventure travel, offering a comprehensive travel program, even in remote locations! Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.