Cycling Puglia – The Heel of Italy

Day 1: Putignano
Day 2: Putignano - Alberobello - Putignano, 21 mi (34 km)
Day 3: Putignano - Polignano a Mare - Monopoli, 31 mi (49 km)
Day 4: Monopoli - Ostuni, 28 mi (45 km)
Day 5: Ostuni - Avetrana, 40 mi (66 km)
Day 6: Avetrana - Sea Loop, 33 mi (53 km)
Day 7: Avetrana - Lecce, 34 mi (55 km)
Day 8: Lecce

Day 1: Putignano
Welcome to Putignano, one of Puglia’s oldest towns, best known for its centuries-old carnival – the longest-running in Europe. The town’s historic center is a maze of medieval alleyways, limestone houses, and charming piazzas. Upon arrival at your accommodation, you’ll receive a warm welcome, complete with a bike fitting and a detailed tour briefing. Your first Apulian experience begins with a wine tasting, where you’ll discover the region’s rich enological traditions. The tasting includes a light aperitif of regional delicacies, from local cheeses to artisanal taralli. If time allows, visit the Museo del Carnevale to learn about Putignano’s mask-making traditions, or stroll through its baroque churches before enjoying authentic Pugliese cuisine.

Sample accommodations: Petrantiche

Day 2: Putignano - Alberobello - Putignano, 21 mi (34 km)
Today’s ride takes you deep into the Itria Valley, a landscape dotted with trulli, the cone-shaped stone houses that make this region famous. Follow the Apulian Aqueduct cycling route (Ciclovia dell’Acquedotto) toward Alberobello, a UNESCO World Heritage Site. As you pedal along country paths framed by ancient olive trees and dry-stone walls, you’ll reach this magical town where more than 1,500 trulli create a fairytale skyline. Wander through Rione Monti and Aia Piccola, the two oldest districts, and enjoy a coffee or gelato before returning to Putignano.

Sample accommodations: Petrantiche

Day 3: Putignano - Polignano a Mare - Monopoli, 31 mi (49 km)
Today, cycle from the rolling hills of Putignano toward the Adriatic coast. Your first stop is Polignano a Mare, a town perched dramatically above limestone cliffs. The birthplace of singer Domenico Modugno (“Volare”), Polignano offers panoramic terraces and sea-view trattorias where you can sample fresh seafood and handmade pasta. Continue along the coastal route to Monopoli, a town blending medieval architecture with seaside charm. Explore its ancient port, baroque churches, and labyrinthine old town before settling in for an evening near the sea.

Sample accommodations: Albergo Diffuso

Day 4: Monopoli - Ostuni, 28 mi (45 km)
Depart Monopoli through a landscape filled with centuries-old olive trees, some dating back over a thousand years. As you move inland, the horizon reveals Ostuni, known as “La Città Bianca” (The White City) for its dazzling whitewashed buildings. Before reaching town, enjoy views of the Adriatic Sea from scenic overlooks. Once in Ostuni, explore its cobblestone streets on a guided Ape Calessino tour, an iconic Italian three-wheeled vehicle that winds through narrow lanes. The evening is yours to enjoy local specialties such as burrata, bruschetta, and regional wines.

Sample accommodations: Laterra Hotel 

Day 5: Ostuni - Avetrana, 40 mi (66 km)
Your longest ride leads through Salento’s red earth landscapes and endless olive groves. Stop in Oria, a medieval gem crowned by a Swabian Castle built by Frederick II and a cathedral topped with a colorful tiled dome. Continue along the Primitivo Wine Route to Manduria, considered the birthplace of the Primitivo di Manduria DOC wine. Visit the town’s 5th-century cathedral, noble palaces, and archaeological park before cycling onward to Avetrana, where you’ll stay at a traditional Masseria (farmhouse). Enjoy a homemade dinner featuring farm-to-table cuisine and local wine.

Sample accommodations: Masseria Bosco

Day 6: Avetrana Sea Loop, 33 mi (53 km)
Today’s loop ride leads to the Taranto province, where golden beaches meet the waters of the Ionian Sea. These shores remain one of Puglia’s best-kept secrets, perfect for a swim or a picnic by the water. In the afternoon, visit a local olive farm for an in-depth olive oil experience. Learn about cultivation, harvesting, and cold-pressing techniques, then enjoy a guided tasting of six distinct olive oils. Return to the Masseria for another authentic Pugliese dinner under the stars.

Sample accommodations: Masseria Bosco

Day 7: Avetrana - Lecce, 34 mi (55 km)
The final ride brings you inland through serene Salento countryside, passing by vineyards and dry-stone walls that define the region’s agricultural heritage. Your destination is Lecce, often called the “Florence of the South” for its elaborate Baroque architecture. Explore landmarks like the Basilica di Santa Croce, Piazza del Duomo, and Roman Amphitheater, and watch the limestone façades glow golden at sunset. This is the perfect finale to your cycling adventure through Puglia.

Sample accommodations: Arco Vecchio

Day 8: Lecce
After breakfast, your Apulian cycling journey officially ends.  

Enhance your trip with a pre-tour stay in Matera, one of the oldest continuously inhabited cities in the world. Discover its remarkable Sassi cave dwellings, carved into limestone cliffs and recognized as a UNESCO World Heritage Site.

The City of the “Sassi”

The city of Matera, a UNESCO World Heritage Site, is world-renowned for its ancient “Sassi” cave dwellings carved directly into limestone cliffs. These remarkable homes, some dating back to the Paleolithic era, were continuously inhabited until the 1950s. Today, many have been beautifully restored and repurposed into boutique hotels, restaurants, and museums, offering a glimpse into a lifestyle that once defined southern Italy’s earliest communities. The surrounding gravine (canyons) create a striking natural backdrop, making Matera one of Italy’s most beautiful destinations.

Day 1: Matera
Upon arrival at your accommodation, you’ll receive a warm welcome, complete with a bike fitting and comprehensive tour briefing to prepare for the days ahead. Once settled, begin exploring Matera’s ancient Sassi districts – Sasso Caveoso and Sasso Barisano – where you can step inside preserved cave dwellings that reveal how families lived for centuries in these rock-hewn homes. If time allows, venture into the Murgia Materana Park, home to over 150 cave churches adorned with medieval frescoes. The area offers scenic trails and panoramic viewpoints overlooking Matera’s stone skyline. As evening falls, visit the Belvedere di Murgia Timone, where the city glows golden at sunset. End your day at a local trattoria savoring Lucanian cuisine, featuring dishes like orecchiette with breadcrumbs, roasted lamb, and the region’s signature bread, Pane di Matera IGP, baked in traditional wood-fired ovens.

Sample accommodations: La Suite Matera

Day 2: Matera - Castellaneta, 37 mi. (60 km)
Departing Matera, today’s route follows quiet country roads through the Parco Naturale Regionale delle Gravine, or Ravines Regional Park, known for its dramatic cliffs and archaeological sites. You’ll cycle past golden wheat fields and olive groves, with occasional glimpses of shepherd huts and stone farmhouses typical of rural southern Italy. Stop in Laterza, a town renowned for its Maiolica pottery and its artisan bakeries, where traditional “Pane di Laterza” is made. Enjoy a coffee or light lunch in the historic center before continuing toward Castellaneta, a peaceful countryside area surrounded by vineyards and orchards. Castellaneta is also the birthplace of silent film star Rodolfo Valentino, and you can visit a small museum dedicated to him if time permits. Spend the evening relaxing in your Masseria, a traditional farmhouse, enjoying views of the rolling Apulian hills under a wide, star-filled sky.

Sample accommodations: Le Grotte di Sileno

Day 3: Castellaneta - Putignano, 34 mi. (55 km)
After breakfast, your ride continues through the Ravines Regional Park, crossing an impressive stone bridge spanning one of the deep canyons that characterize this region. As you leave the rugged landscape behind, the terrain softens into the classic scenery of Puglia’s heartland: dry-stone walls, olive trees, vineyards, and trulli, the cone-roofed limestone huts unique to this area. Approaching Putignano, you’ll start to see more of these traditional trulli structures dotting the countryside. Putignano itself is a town steeped in history and famous for hosting Europe’s oldest carnival, dating back to 1394. Its historic center is a maze of baroque churches, narrow alleys, and lively piazzas, perfect for an evening stroll. Conclude the day with dinner at a local osteria, sampling Pugliese specialties such as handmade orecchiette with turnip greens, local cured meats, and a glass of Primitivo wine, a proud symbol of Apulian viticulture.