The Land of Trulli
We were introduced to this corner of Italy by one of our Italian guides who lives in the region and has long boasted of its stunning scenery, ancient traditions, and some of the best food. With the Adriatic as a back-drop, quiet roads to cycle, and fascinating sites including the enigmatic trulli in Alberobello, we were easily convinced to create a trip. Beginning in Monopoli and finishing in Otranto, you’ll see the best of this region all the while enjoying distinctive lodging and exquisite meals. Buon appetito!
Only Great Explorations:
“Puglia is natural and wild, authentic in the true sense, rustic and traditional, friendly and safe. It is totally enchanting if these are the qualities you are searching for in a place” — Written by a traveller who fell in love with Puglia and stayed.
Puglia is one of our most popular trips for good reason. It appeals to people because of the climate but also the fact that the towns and villages are so appealing. The roads in Puglia and much of southern Italy may not match the pristine condition of Tuscany for example, but they add a touch of rugged charm to the journey. While our routes are generally peaceful, you might encounter the odd rough patch and occasional litter, especially near small villages. However, these are minor and are offset by Puglia’s beautiful countryside and warm hospitality.
In Puglia, we choose to stay outside of towns on certain days for several reasons. Staying at a masseria in the countryside offers many advantages: the roads are quieter, making it easier to travel to and from the property compared to staying in a city centre like Monopoli or Otranto. Additionally, masserias often feature large swimming pools and other amenities that city centre hotels typically don’t offer. All of the these properties have restaurants but in some locations we choose to dine outside the property at a superior restaurant.
Finally, our itinerary allows you to see and experience each of Monopoli, Locorotondo, Ostuni, and Otranto — perhaps the gem of the region. We take a train from Ostuni to Squinzano to bypass Brindisi and cycle along the coast, right to Otranto and our hotel there. On the final day, we get to ride south along the coast — a magnificent ride.
Straight Talk
Capitolo
Day 1+2
Locorotondo
Day 3
Ostuni
Day 4
Otranto, Province of Lecce, Italy
DAYS 5+6
| 2026 | 2027 |
|---|---|
| Apr 18-24 | Apr 17-23 |
| May 9-15 | May 8-14 |
| May 16-22 | May 15-21 |
| Jun 6-12 | Jun 5-11 |
| Jun 13-19 | Jun 12-18 |
| Sep 19-25 | Sep 18-24 |
| Oct 4-10 | Sep 25-Oct 1 |
| Oct 2-8 |
Custom trips are also available and can start any date, call or email for details.
Trip Size
Total Days
Arrive/Depart
Activity LevelModerate
Average daily distance: 40-65 km
Van supported
Terrain2 days are flat; 2 days are gently rolling; 2 days are moderately rolling
CostLand Cost
US $3,150
Includes 6B/2L/5D
Single Supplement
US $800
Bike Rentals
Hybrid Bikes: US $320
Racing Bikes: US $420
E-bikes*: US $480
Pre-trip Extension in Monopoli
US $495
Includes two nights stay at Palazzo Indelli, transfer to hotel on arrival from Bari or Monopoli, 1/2 day walking tour, and transfer to Casale del Murgese for the start of the trip
Post-trip Extension in Lecce
US $595
Includes two nights stay at Patria Palace Hotel and 1/2 day walking tour
*E-bikes are generally available but are on an ‘on request basis ‘ and will be confirmed on receipt of your booking registration. E-bikes provided are the best rentals available in the region. Our regular fleet of hybrid and race bikes are fun to ride and light and fast, but if having an e-bike will make your trip, we’ll do our best to provide. E-bike rentals are non-refundable.
Getting There
Our trip starts from the Casale del Murgese, located 15 km from Monopoli. The nearest train station is Fasano and if you are travelling by train from Rome or Bari, it is the stop after Monopoli. The shuttle from Fasano takes 5 minutes and we will meet you on arrival. If you are considering arriving a day early, consider our Extension with a night in historic Monopoli, where you can stroll to restaurants and cafes.
Savelletri di Fasano
We’ll meet at our first hotel at 2 p.m., where our guides will fit your bikes.
Let’s go cycling! Today’s ride is a loop to Egnazia, a Roman port city dating back to the 5th century, where remnants of the ancient road to Rome, a beautiful acropolis, and other monuments still exist. We’ll visit the museum here to learn more about this fascinating history. Take a swim at the hotel in the late afternoon, then join us for a wine reception before dinner.
Distance: 20 km; elevation gain: 84 m or 29 km; elevation gain: 124 m
Savelletri di Fasano
There are several options today, each beginning with a ride to historic Monopoli, which boasts a charming historic centre and a vibrant port where fishermen bring in the day’s catch. Visit the impressive 16th-century castle, explore the shops, and enjoy the restaurants in the centre.
A shorter option leaves Monopoli heading west through small villages, with a lunch option at a favourite restaurant before cycling back to the hotel. Prefer a longer ride with some moderate hills? Polignano a Mare and/or Conversano are both worth visiting, with historic centres and excellent restaurants to tempt you. We will dine tonight at a seafood restaurant popular with locals.
Distance: 35 km; elevation gain 173 m or 55 km; elevation gain: 430 m or 77 km; elevation gain 600 m
Locorotondo
We’ll cycle to the UNESCO World Heritage Site of Alberobello, which boasts more than 1,500 trulli — distinctive round stone buildings with conical slate roofs. We’ll join a local guide here to learn the secrets of this fascinating town on a walking tour, followed by lunch together.
The short option will take you directly to Locorotondo, known as the “Balcony of the Itria Valley” for its stunning views. Puglia produces 17% of Italy’s wine, and the region’s white wines are particularly popular. You can sample wines from more than 1,000 vintners at the Cantina Sociale in town. A longer option will take in the Bosco delle Pianelle Nature Reserve.
We’ll stay at a charming hotel featuring a collection of private suites in the historic centre of town. For dinner, we’ll follow the locals to a charming trattoria. Try the house pennette, quill-shaped pasta in a hearty tomato sauce spiked with hot peppers and onions, or the lamb chops with cheese, parsley, and wild herbs.
Distance: 44 km; elevation gain: 695 m or 75 km; elevation gain: 947 m
Ostuni
Start your day cycling to Martina Franca, an ancient city with stone walls, stunning piazzas, and tiny winding streets. En route, you’ll pass through olive groves, vineyards, and forested landscapes on quiet roads with very little traffic. Midway, we’ll have time to explore Cisternino, with its great cafés and restaurants. We’ll finish the day in Ostuni, known as the “White City,” with its Arab-influenced architecture and labyrinth of streets designed to confuse invaders (we’ll show you the easy way in). Tonight, we’ve arranged a cooking class at a local restaurant, where you’ll enjoy the Apulian specialties you prepare.
Distances: 36 km; elevation gain: 489 m or 46 km; elevation gain: 498 m
Otranto
This day will start with a transfer by local train to Squinzano, followed by a coastal ride with the aquamarine Adriatic at your side. The seaside town of San Foca awaits you for lunch, and afterwards, we’ll continue south to historic Otranto, the most easterly point on the Italian peninsula and one of our favourite cities in the region. Like much of Puglia, Otranto has a colourful past, with Greek, Byzantine, Roman, and Aragonese influences. We’ll stay at Masseria Bandino, located just outside of town, with a large swimming pool and beautiful grounds. Tonight will be a free evening for dinner, there are many excellent restaurants to choose from in Otranto’s centre.
Distance: 70 km; elevation gain: 317 m
Otranto
We save the best ride for last! Cycle south along the dramatic coastal road to Santa Cesarea Terme, surrounded by unparalleled architectural and natural beauty in one of Italy’s most serene locations. There will be opportunities to swim along the way, as well as some of the most stunning scenery in Italy. For those who want a challenge, you can continue all the way to Marina di Leuca, at the “southern tip of the boot,” and back for a century ride. Those who prefer a shorter ride can cycle directly back to Otranto after lunch, where you can explore the Castello Aragonese, a mighty fortress that once formed part of the city’s defenses, or relax around the hotel pool.
We’ll finish the day with a wine tasting hosted by a local sommelier, followed by a celebratory dinner in the hotel dining room.
Distance: 45 km; elevation gain: 459 m or 109 km; elevation gain: 1,356 m
Depart
After breakfast, we provide a shuttle to the train station in Lecce by 10 a.m. for onward travel.
This historic upscale property overlooks the Adriatic Sea and sits on lush farmland in an oasis of tranquility. Individually decorated guest rooms, a restaurant with open-air dining and infinity swimming pool make this a cool hotel.
This hotel comprises a group of historic and beautifully appointed apartments or casas, each unique and distinctly renovated. It’s located in the old town centre and walking distance to everything.
Occupying a 13th century palace, adjacent to St. Peter’s Benedictine monastery, this family-run hotel sits in the centre of Ostuni. It houses a wonderful restaurant and a charming bar built out of quarried stone.
This former 17th-century manor house sits on 5 hectares of park, features an outdoor pool and large comfortable rooms. The surrounding area is rich in olive trees, citrus plantations, and the Salentine beaches.
Tour Reviews
This was probably the best vacation I have ever had. Well planned with interesting activities besides the biking. Well done.
The guides were great and gave it their all!!! Their choices of locations to visit as well as restaurants were awesome. Fabulous way to experience a country!!
Puglia was beautiful, as expected. Dinners, wine tasting, tour of Trullis, and cooking class were wonderful.
Great trip. Nice quiet roads and lots of riding and side trip.
It was just fabulous. I had a wonderful time. I had never been on a bike trip before but now I want to go on many more.
The tour guides provided a good mix of biking, interesting sites and good food.
“Italian food was fabulous. Guides were great. Hotels were very nice. We loved the scenery.”
“Puglia was a beautiful place to cycle for this time of the year. Gabiele and Davide were outstanding- encouraging, supportive, and they made the entire trip simply amazing!. All accommodations were great. Loved the coffee stops along the way – it made the cycling more enjoyable.”
“It was amazing, loved the whole trip. Puglia is beautiful and our route was fantastic. Bianca and Nico were the best, they worked well together, they were always up beat. My favourite was the first- Hotel Masseria Garrappa. I loved the setting, the style of hotel, my room, the beautiful garden eating area. Best meal at Masseria Garrappa. Pietro was amazing with the two tours, the museum and Trulli houses. We had a special trip the last day, we did a boat trip to look at Grotto rather than go in the caves. Maps were good. The riding options were great as were our guides who were so accommodating. Van & mechanical support were all excellent. We could not have asked for better.”
“I loved riding my bike!!! And the variety of the terrains we rode through. Loved the Masserias. The two events I particularly enjoyed were the trullis and the archeological museum with the guide Pietro. I was fortunate that you allowed us to have a boat tour to visit the caves. All 4 of us had previously visited several caves in Europe, so this was new and enjoyable. The riding level and distances were just right for me. The van was always in the right place at the right time. Our guides tech support was excellent!”
“This trip certainly met my expectations since I had not done a bike trip previously. Before embarking, I felt confident I would be impressed with the tour and I was not disappointed in the least. Lovely hotels. Having at least one close or in a town was appreciated (La Terra in Ostuni), and the peace and quiet of the ones in the country side was also good. All meals were delicious but I especially enjoyed the final dinner at Masseria Bandino. All trip events were excellent and exceeded my expectations mostly due to Pietro’s knowledge and fabulous presentation. I very much enjoyed learning about local culture, history and farming practices. Route was very good and I enjoyed the different terrain experienced each day. Excellent and very attentive van support. Bike was great.”
“I loved the last day and the day in the upland nature reserve. Loved the historical hotels, with beautiful common rooms and courtyards. Loved breakfasts in Monopoli. Daily distances and level of difficulty were as expected. Van was available when I needed it.”
“I was very happy with the trip. We had some interesting and enjoyable side tours such as a museum, olive oil refinery and wine tasting event. The guides were flexible to the needs of all riders which makes cycling with Great Explorations an enjoyable experience. I like not having to worry about travel logistics because you can trust your guides to take care of your needs and ensure you have an enjoyable experience.”
“Repeat trippers with GE! They scout out really interesting and scenic routes for cycling; accommodations are top notch as are their dining locations. The guides were great, friendly and had our safety and concerns at their forefront. They were able to adjust as circumstances presented and ensured that everyone’s expectations were met or exceeded. Full marks to them. We will ride again with GE!”
“Beautiful region – very unique. Logistically well organized. Hotels were great. The freedom to ride at our own pace was nice. Guides were quick to address any issues or requests.”
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