Chat with us on WhatsApp. We're just a message away.Self-Guided
at your own pace
7 days
86 km
~12 km/day
easy to moderate
Otranto
ends Matera
2–12
participants
Casual+ Inns (4★)
May – Jun, Sep – Oct
Discover southern Italy's hidden treasures on this immersive walking journey through Puglia and Matera. This culinary-focused adventure takes you from the coastal town of Otranto to the ancient cave dwellings of Matera, a UNESCO World Heritage Site. Along the way, experience authentic food traditions through cheese-making workshops, olive oil tastings, cooking classes, and wine therapy. Walk through baroque Lecce, wander among millenary olive groves, explore the trulli houses of Alberobello, and traverse the dramatic landscape of rock churches. Each day combines moderate walking with hands-on cultural experiences that engage all five senses, offering an intimate look at Puglia's rich gastronomic heritage and architectural wonders.
Highlights
Experience Puglia's renowned food traditions firsthand through cheese-making workshops, olive oil sommelier tastings, cooking classes, and wine therapy treatments. Each day offers hands-on encounters with local artisans and producers who share their time-honored techniques.
Discover two UNESCO-recognized treasures: Alberobello's unique trulli houses with their distinctive conical roofs, and the ancient Sassi di Matera, one of the world's oldest continuously inhabited settlements carved into limestone cliffs.
Walk through the baroque splendor of Lecce's historic center and explore dramatic Mediterranean coastlines featuring wind-carved cliffs, hidden bays, and timeless scenery along Otranto's southern shores.
9 Days from $2,995
Free cancellation · Up to 60 days before group departure
| Day | Place | Casual+ Inns | Meals | Distance | Activity |
|---|---|---|---|---|---|
| 01 | Otranto | Palazzo Papaleo (5-star) | D | - | |
| 02 | Otranto | Palazzo Papaleo (5-star) | B | 11 km / 7 mi | hiking |
| 03 | Lecce | Palazzo Bignami (4-star) | B | 13 km / 8 mi | hiking |
| 04 | Ostuni | Hotel Rione Antico La Terra (4-star) | B, D | 7 km / 4 mi | hiking |
| 05 | Montalbano | Masseria Ancella | B | 12 km / 7 mi | hiking |
| 06 | Locorotondo | Sotto Le Cummerse | B | 15 km / 9 mi | hiking |
| 07 | Locorotondo | Sotto Le Cummerse | B | 19 km / 12 mi | hiking |
| 08 | Matera | Casa di Lucio | B | 9 km / 6 mi | hiking |
| 09 | Departure | - | B | - |
Meals: B = Breakfast · L = Lunch · D = Dinner
Listed hotels are subject to availability and may be replaced with similar alternatives.
Begin your journey with an exploratory stroll through Otranto's historic center. Pass through Porta Alfonsina, the ancient gateway that leads into the old town's timeless streets. Wander the atmospheric alleys and admire the medieval architecture before settling in for your first evening. Dinner is included tonight, offering a taste of local Puglian cuisine to start your culinary adventure.
Meals: D
Accommodation: Palazzo Papaleo (5-star)
Meet your guide after breakfast for an authentic dairy experience. Visit a traditional cheese-making facility where you'll walk with the master cheesemaker through each stage of production, followed by a generous tasting of local cheeses and specialties. Afterward, your walk continues along Otranto's southern coastline, where wind-sculpted cliffs, hidden coves, and rocky bays create a dramatic Mediterranean landscape frozen in time.
Meals: B
Hiking Distance: 11 km / 7 mi
Accommodation: Palazzo Papaleo (5-star)
Walk independently through the lush Idro valley, passing the historic Le Costantine Foundation. Continue to La Cutura Botanical Garden, home to several themed gardens showcasing over three thousand succulent species. A private transfer brings you to Lecce, the city's extraordinary baroque architecture and winding historic lanes. In the afternoon, participate in a traditional papier-mâché workshop, learning the craft that has defined Lecce's artisan heritage for centuries.
Meals: B
Hiking Distance: 13 km / 8 mi
Accommodation: Palazzo Bignami (4-star)
Depart Lecce for Masseria il Frantoio, nestled among ancient olive groves on the Puglian plains. Tour the underground mill and walk through the centuries-old olive grove before participating in an expert-led tasting of organic extra virgin olive oils. Walk the ascending paths to Ostuni, known as the White City for its stunning whitewashed buildings. After free time to explore, enjoy a cooking class and dinner at a traditional restaurant in the beautiful historic center.
Meals: B, D
Hiking Distance: 7 km / 4 mi
Accommodation: Hotel Rione Antico La Terra (4-star)
Transfer from Ostuni to the Sanctuary of Sant'Oronzo, surrounded by natural beauty. Stop at a family-run farm along the route for a coffee break and tasting of local specialties to energize your walk to the masseria. The afternoon is dedicated to Wine Therapy, an innovative wellness experience featuring beauty treatments using wine and must extracts, rich in antioxidants that combat aging and detoxify the skin.
Meals: B
Hiking Distance: 12 km / 7 mi
Accommodation: Masseria Ancella
After breakfast, transfer to Cisternino before beginning your walk. The route from Cisternino to Locorotondo follows portions of the historic Apulian Aqueduct's path. Arrive in Locorotondo, a charming village distinguished by its distinctive pointed-roof houses. Sample excellent local wines in an intimate, well-curated wine shop tucked among the town's picturesque streets, learning about the region's unique varietals.
Meals: B
Hiking Distance: 15 km / 9 mi
Accommodation: Sotto Le Cummerse
Begin walking from Martina Franca toward Alberobello, the heartland of trulli architecture. These unique conical limestone dwellings have earned Alberobello UNESCO World Heritage recognition since 1996 for their architectural significance and historic importance. To fully appreciate Puglia's most distinctive architecture, enjoy a traditional aperitif inside an authentic trullo before transferring back to Locorotondo for the night.
Meals: B
Hiking Distance: 19 km / 12 mi
Accommodation: Sotto Le Cummerse
Walk through the Natural Park of Rock Churches surrounding Matera. Cross the suspension bridge spanning the Gravina stream, which connects the Murgia plateau to the ancient Sassi district. The bridge offers both an adventurous thrill and spectacular views of Matera's cave dwellings rising from the gorge below. Arrive in one of the world's oldest continuously inhabited cities, where ancient stone houses climb the ravine walls.
Meals: B
Hiking Distance: 9 km / 6 mi
Accommodation: Casa di Lucio
Matera ranks among the world's most ancient cities, preserving evidence of Italy's earliest human settlements. The Sassi di Matera, a complex of cave dwellings carved into the limestone cliffs, received UNESCO World Heritage designation in 1993. After exploring this remarkable city at your leisure, transfer to the airport for your departure.
Meals: B
Each accommodation has been thoughtfully selected to ensure an exceptional and memorable experience for guests. Should the listed hotel be unavailable, we will ensure an alternative of similar quality.
A luxury boutique hotel located in the historic center of Otranto, just opposite the cathedral and close to the sea. The hotel combines elegant historic architecture with modern comfort and offers panoramic terrace views of the Adriatic coast.
An elegant boutique hotel featuring sophisticated interiors and spacious accommodations. Perfect for guests looking for a refined, luxurious, and memorable stay experience.
A historic hotel located in the heart of Ostuni’s old town, surrounded by whitewashed streets. Offers refined interiors and a tranquil ambiance, perfect for a peaceful getaway.
Lodging
All hotels as mentioned in the tour details or similar (subject to availability).
Luggage Transfer
Transportation of luggage from one hotel to another.
Airport Pickup
Enjoy a hassle-free group airport pickup to start your journey. Available only on the tour start date.
Airport Drop
Enjoy a hassle-free group airport drop to finish your journey. Available only on the tour end date.
Meals
Meals as per itinerary. Guests are given the opportunity to dine on their own so that they discover a location independently.
• 8 nights accommodation with breakfast • Transfer IN & OUT Bari/Brindisi Apt •Dinner day 1 •Guided walking excursion day 2 •Dairy visit and local cheese tasting day 2 • Entrance at the Botanical Garden day 3 • Lecce walking guided tour day 3 •Papier-mâché workshop day 3 •Olive oil tasting and visit day 4 •Cooking Class with dinner day 4 •Coffee break day 5 •Wine therapy day 5 •Wine tasting with Aperitivo day 6 and 7 •Scheduled Private transfers • Travel App (maps, tracks, route notes) • Luggage transportation hotel to hotel •Hotel tourist taxes •Phone assistance 08:00-20:00
Beverages
Beverages such as alcohol, tea, coffee, juice at a hotel or restaurant.
Gratuity
Gratuities for your guide team are not included in the trip price.
Otranto
Matera
Bari Karol Wojtyła Airport (BRI) or Brindisi Airport (BDS)
Bari Karol Wojtyła Airport (BRI) or Brindisi Airport (BDS)
Arrival
Arrivals for the tour take place via Bari Karol Wojtyła Airport (BRI) or Brindisi Airport (BDS). From either airport, a pre-arranged transfer is included to take guests to Otranto, the starting point of the tour. There is no fixed arrival time on Day 1, offering flexibility to travelers. Hotel rooms are generally available from 3:00 PM onwards, allowing guests to settle in comfortably before beginning their experience.
Departure
The tour concludes in Matera, from where a transfer to either Bari or Brindisi airport is included in the package. After breakfast and check-out, guests are transferred to the airport for their onward journey, ensuring a smooth and well-organized departure.
The best time for walking in Puglia is during spring (April-May) and fall (September-October) when temperatures are mild and comfortable for daily walks, typically ranging from 15-25°C.
Summer (June-August) can be hot with temperatures reaching 30°C or higher, though coastal breezes provide relief.
Winter (November-March) is mild compared to northern Europe with temperatures around 10-15°C, making it suitable for walking, though some days may be rainy.
The tour operates from mid-February through November, with peak season in July-August and the most pleasant walking conditions in May-June and September-October.
January
Mixed
February
Mixed
March
Mixed
April
Good
May
Best
June
Best
July
Offseason
August
Offseason
September
Best
October
Best
November
Good
December
Mixed
Packing wisely ensures comfort and safety on your hiking adventure. This list covers essential hiking gear, clothing, and travel items to help you handle varied terrain and weather conditions.
Please limit your luggage to one medium-sized suitcase and one daypack. Mark your luggage clearly with your name, address, and phone number.
EU citizens can travel with a national identity card, though some international airlines may require a passport. Non-EU members should check visa requirements for Italy. A European driving license is valid throughout the EU; non-EU drivers need an international license. European Economic Area residents should obtain a European Health Card before traveling.
Medical insurance that covers medical costs in case of an accident during the trip is mandatory to participate in our tours.
We recommend purchasing adequate travel insurance to protect yourself from unforeseen events. Our experience shows that guests who purchase travel insurance, including coverage for all activities on the itinerary, trip cancellation, interruption, delay, baggage damage, loss or theft, personal accident, death and repatriation costs, medical and emergency expenses, and personal liability, travel with greater peace of mind.
Is proof of medical insurance required?
Yes. You must provide your insurer's name, policy number, and emergency contact through our reservation form. If you cannot provide proof, you'll need to purchase insurance before traveling with us.
Can I use my credit card insurance?
Yes, as long as it meets our requirements and provides adequate coverage. Keep your emergency contact number and policy number accessible while traveling.
When should I buy travel insurance?
Purchase travel insurance as soon as you've paid in full or booked your flights.
Does Art of Bicycle Trips sell travel insurance?
We do not sell travel insurance directly. We recommend comparing policies and choosing the one that best fits your needs. A useful place to start is Insured Nomads.
The walking routes are easy and suitable even for children with minimal walking aptitude. The itineraries mainly follow paths and low-traffic roads, with some passages on busier roads and occasional more technical sections. Daily distances range from 7 to 19 km with moderate elevation gains.
We recommend comfortable walking shoes, a hat, trekking poles, drinking water, sun cream, a swimsuit, and a waterproof jacket in case of rain.
Your luggage will be transported between hotels during daily activities. Only one piece of luggage per person up to 20 kg is accepted. Bags should be ready by 9:00 AM and will be delivered to your next hotel by 5:30 PM. Luggage labels will be provided during the welcome briefing.
Breakfast is included daily. Additionally, dinner is included on Day 1 and Day 4. Various food experiences are included throughout, such as cheese tastings, olive oil tastings with lunch, cooking class with dinner, coffee breaks, and wine tastings with aperitivo.
Yes, dietary requirements can typically be accommodated. Please inform us of any dietary restrictions when booking so arrangements can be made with restaurants and food experiences.
The Travel App provides maps, GPX routes, points of interest, and real-time position tracking. It works offline to save battery and data. The app is available in English and can be downloaded for free. A shortcut code will be provided in your service list.
