Cycling Puglia’s White Villages Plus! the Salento

  • Length 11 days
  • From USD$6250
  • Style/Level Classic 2.0
  • Countries Italy
  • Begin/End Matera / Lecce
See related tours

Beautifully situated on the Adriatic Coast between the spur and heel of Italy’s “boot” lies Puglia. Nestled against the brilliant blue of the Mediterranean ancient Greek and Italian cultures mingle among hillside vineyards, olive groves, and whitewashed villages. Join us as we begin our bicycling journey in Matera, a world renowned UNESCO World Heritage Site, where dwellings carved into limestone caves create an enchanted and ancient stone city. We’ll pedal east toward Alberobello, another UNESCO World Heritage Site, through a landscape filled with unique conical shaped dwellings known as trulli. Continue to the striking “Città Bianca” or “White City” of Ostuni before heading south to Grottaglie, famed for its ceramics, and the important coastal towns of Gallipoli and Otranto where you’ll revel in impromptu stops at some of the beautiful beaches that attract visitors from all over Italy. Our final stop brings us back inland to Lecce, the baroque Florence of Southern Italy where palatial streets welcome us. Along the way you’ll enjoy meals prepared with Italian, Greek, and Middle Eastern influences and discover the warmth and hospitality of Southern Italy’s friendliest people.

If this sounds great but you prefer a shorter ride check out the 7-day Cycling Puglia’s White Villages.


  • UNESCO World Heritage Sites – Sassi of Matera and trulli of Alberobello, White city of Ostuni, Cheese tasting, Locorotondo, Ancient olive mill visit, Via Traiana, Otranto, Lecce – the baroque Florence of Southern Italy, The tip of the heel of Italy’s boot, Grottaglie and its ceramics


  • 11 days, 10 nights accommodation

  • meals as noted in itinerary

  • guided visit of Matera

  • guided visit of Alberobello

  • 1 cheese tasting

  • and olive mill visit

  • All Classic tour inclusions

Keep in mind

We work hard to maintain consistency across all of our tours, but some trips have unique differences. Here are some things to keep in mind about this tour.

There is a van shuttle on Day 3 and 7.

Date Price Private room fee Note
Sep 22-Oct 2, 2024 USD$5850 USD$650 One space remaining!
Sep 29-Oct 9, 2024 USD$5850 USD$650 Sold out! Wait list available.
Apr 20-30, 2025 USD$6250 USD$650 Book now and save $200 per person.
May 4-14, 2025 USD$6250 USD$650 Book now and save $200 per person.
Sep 7-17, 2025 USD$6250 USD$650 Departure confirmed to go! Book now and save $200 per person. One Recycle discount available. 
Sep 21-Oct 1, 2025 USD$6250 USD$650 Book now and save $200 per person.
Sep 28-Oct 8, 2025 USD$6250 USD$650 Book now and save $200 per person.
DateSep 22-Oct 2, 2024
Private room feeUSD$650
NoteOne space remaining!
DateSep 29-Oct 9, 2024
Private room feeUSD$650
NoteSold out! Wait list available.
DateApr 20-30, 2025
Private room feeUSD$650
NoteBook now and save $200 per person.
DateMay 4-14, 2025
Private room feeUSD$650
NoteBook now and save $200 per person.
DateSep 7-17, 2025
Private room feeUSD$650
NoteDeparture confirmed to go! Book now and save $200 per person. One Recycle discount available. 
DateSep 21-Oct 1, 2025
Private room feeUSD$650
NoteBook now and save $200 per person.
DateSep 28-Oct 8, 2025
Private room feeUSD$650
NoteBook now and save $200 per person.

Download Itinerary

We’ll send you a link to a full day by day tour itinerary that can be downloaded and printed so you can review all the details online and offline. This packet also includes details about what to expect on tour and arrival and departure details.
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  • Total distance 422 km (260 miles)
  • Average daily distance 47 km (29 miles)
  • Tour style Classic
  • Tour level 2.0

Highlights: Welcome drink, bike fitting, dinner in the “Sassi” of Matera

Arrive in Matera, unique in all of Italy for the cave dwellings that ring the central city. Inhabited by refugee clerics and monks from Greece and the Balkans during the 8th and 9th centuries, the cave churches and domestic dwellings carved into the town’s calcarenite or semi-sandstone cliffs at one time housed as many as 25,000 people. Today, the churches and caves are preserved as a World Heritage Site as being the “most outstanding, intact example of a cave-dwelling settlement in the Mediterranean.” Settle into our hotel and enjoy our welcome dinner after fitting bikes.

Meals : Dinner
Lodging : Hotel San Domenico

Highlights: Guided walk of the Matera’s “sassi”, Appian Way

We’ll start the morning with a loop ride exploring Matera’s surroundings. Sights along the way include the fortified Massaria Jesce, which was an ancient Roman “post office” on the Appian Way – one of the most important Roman Roads. We’ll also visit the cave crypt of San Michele Arcangelo with frescoes dating to the 14th century. This afternoon features a guided walk exploring Matera’s history including a typical sassi, a cave dwelling house. Fodor’s has described the sassi as “one of the most unique landscapes in Europe,” on this tour we’ll gain a better understanding for the living conditions of what is believed to be one of the first human settlements in Italy.

Meals : Breakfast
Lodging : Hotel San Domenico

Highlights: Trulli, vineyards, mozzarella demo and tasting

Today we shuttle from Matera to Gioia del Colle, famous for one of Frederic II castles. Start cycling and enjoy a ride through olive groves and vineyards on the way to the “Valle d’Itria” which is the heart of Puglia’s trulli region. Trulli are conical shaped dwellings unique to this part of Italy. Originally used as storage sheds for farmers, they quickly became popular as temporary shelters. Our destination is the small but vibrant town of Locorotondo, our home for the next two nights. At lunch together, we’ll learn more about and sample the fresh mozzarella, burrata and stracciatella for which Puglia is renowned. This afternoon get lost in the whitewashed maze of lanes and historic buildings towering over them.

Meals : Breakfast, Lunch, Dinner
Lodging : Hotel Leonardo Trulli Resort

Highlights: Guided tour of Alberobello and trulli

We’ll pedal to the iconic “trulli” town of Alberobello where we’ll have a guided tour to learn more about these conical shaped buildings and the people who built them. Take time to explore this unique town and have lunch on your own before you bicycle back to Locorotondo.

Meals : Breakfast, Dinner
Lodging : Hotel Leonardo Trulli Resort

Highlights: Ostuni – La cittá bianca

Our ride today will take you first through vineyards and olive groves to the whitewashed town of Ostuni. Our hotel is located in the center of this amazing village which spans three hilltops and is crowned by a Gothic cathedral. Destroyed by Hannibal during the Punic Wars in 1st and 2nd Centuries BC, Ostuni was rebuilt by the Greeks and takes its name from them as “Astu néon or “new town”. Rebuilt by the Normans in the 10th Century, Ostuni then flourished during the Italian Renaissance under Duchess Isabella of Bari. This is an imposing and beautiful city from afar and within.

Meals : Breakfast
Lodging : Ostuni Palace

Highlights: Ancient olive mill, the beach, Carovigno

We’ll take a loop ride from our hotel today to the Adriatic Sea coast. The first stop will be to visit an underground olive press dating to pre-Roman times and used until the 19th C. Our ride continues on the Via Appia Traiana just before reaching the Adriatic Coast. Built by order of the Roman Emperor Traiano in the 2nd century A.D., the Via Traiana connected Rome to Brindisi, one of the most important ports for commerce with the Middle East. We’ll parallel the coast today with a possible dip at a local beach before continuing to the medieval town of Carovigno and back to our hotel.

Meals : Breakfast, Dinner
Lodging : Ostuni Palace

Highlights: Ceramics of Grottaglie, Ionian Coast, ancient Gallipoli

It’s a relaxing and pleasant ride this morning to Grottaglie, Puglia’s most famous pottery town. Be sure to visit one of the many local studios and learn about their painting and firing techniques. The abundant clay in this area, has long been an economic driver for the town. During the 18th century, there were over 42 ceramic related companies in Grottaglie which employed more than 5,000 people. Once your pottery curiosity has been satisfied, we’ll have lunch together in a typical osteria in Grottaglie before shuttling to the coastal town of Gallipoli. Our hotel is located near the heart of old Gallipoli, a small island connected to the mainland by a bridge.

Meals : Breakfast, Lunch
Lodging : Hotel Palazzo del Corso , Relais Corte Palmieri

Highlights: Scenic beaches, coastal towers

We’ll leave the small island city of Gallipoli to pedal along the Gulf of Taranto, the largest gulf in the Ionian Sea. Our ride today explores the Salento, home to a wide variety of beautiful beaches including the “Salento Maldives” which resembles the tropical islands so much they’ve been named after them. We encourage you to stop and take a swim along the way! Our lodging tonight is in Santa Maria di Leuca, the town at the very bottom of the “heel” of Italy.

Meals : Breakfast, Dinner
Lodging : Hotel L’Approdo

Highlights: Riding along the Adriatic Coast, and between ancient fortresses and guard towers, Otranto

Upon leaving the small town of Leuca, you can continue south to land’s end and the sanctuary Santa Maria di Leuca, or start your journey north. Our route to Otranto is along the jagged coast, dotted with karstic caves and ancient defense towers or castles. Arrive in Otranto, historically one of the most important trading cities in Puglia. Enjoy the seafront promenade and the city perched on the waterfront.

Meals : Breakfast
Lodging : Hotel Otranto Corte Di Nettuno

Highlights: Lecce, nature reserve

Continue pedaling north along the coast in between defense towers and scenic cliffs. Our route also includes a car-free section through a nature reserve before turning inland to reach our final destination, arguably Puglia’s most beautiful city – Lecce. Also known as the baroque Florence of Southern Italy, Lecce’s pink sandstone buildings and pedestrian city center make for an inviting afternoon of exploration. This evening, we’ll celebrate the end of our journey with a farewell dinner.

The Sept 29 Departure will stay at Pollicastro Boutique Hotel.

Meals : Breakfast, Dinner
Lodging : Suite Hotel Santa Chiara Lecce , Pollicastro Boutique Hotel

Highlights: Buon viaggio!

We’ll say good-bye after breakfast today. Spend an extra day exploring Lecce, or just enjoy some R&R back on the coast. Whatever you decide, thanks for cycling Puglia with us.

Meals : Breakfast

Visit our Tour Level page to learn more about terrain levels and how we determine day and tour levels.

Pre-trip planning checklist

Italy travel planning page

  • Scenic ride through a very historical area. Tours explained the history

    Alec B., Gardnerville, NV – October 2023
  • Level of difficulty was as described. The region was wonderful to explore and not overcrowded with tourists. So much history in Puglia so the excursions were terrific. Loved riding near the coast.

    Beverley T., Vancouver, Canada – September 2023
  • An intimate experience of the geography, history, and culture of the Puglia region.

    Jo-Ann H., Aldergrove, Canada – September 2023