The Land of Trulli
Puglia is a land of dazzling light, historic villages, a vast blue sea. Orchards, olive groves and vines cover the landscape and quaint villages of whitewashed homes and fairytale-like trulli invite discovery. Cycling along the Adriatic coast is sublime and the cuisine, with abundant fresh seafood and imaginative pasta dishes are the reward for each day’s journey. Best of all are the people, who have lived here away from the rush of life in other parts of Italy, eager to welcome you into their hearts. Benvenuti!
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
Savelletri di Fasano
Day 1+2
Locorotondo
Day 3
Ostuni
Day 4
Otranto, Province of Lecce, Italy
DAYS 5+6
Lecce, Province of Lecce, Italy
Extension Day 7+8
| 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 |
| Sep 27-Oct 3 - PRIVATE | Sep 25-Oct 1 |
| Oct 4-10 | Oct 2-8 |
Trip can start at any date. Custom and self-guided trips also available. Call or email us for details.
Trip Size
Total Days
Arrive/Depart
Activity LevelModerate
Average daily distance: 40-65 km
Van supported
Terrain3 days gently rolling; 3 days are moderately rolling
CostLand Cost
US $3,950
Includes 6B/2L/5D
Single Supplement
US $1,000
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 Risorgimento Resort 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, an upscale restaurant with open-air dining, an infinity swimming pool, and a great location make this hotel ideal.
This masseria style hotel boasts authentic trullis and villa rooms with contemporary touches. Other amenities include a large outdoor saltwater pool, a hot tub and a garden, plus a restaurant and a bar. Unwind with a massage or stretch it out with a yoga class.
“A romantic, stylish and refined hotel that features modern comforts and excellent personal service. Beautiful airy bedrooms in whites and pastels with ethereal drapes. Wonderful restaurant, roof top terrace and private beach just a few kilometeres away. The perfect romantic getaway. ” - HG.
Located just outside of Otranto, this luxurious masseria was built in 1878, originally as a monastery. Lovingly restored with attention to its historical significance, and surrounded by orchards with a large pool in its courtyard, this is a lovely hotel to finish our journey.
Tour Reviews
The Puglia trip was spectacular with incredible scenery, food and local culture.Our guides, Guido and Bianca, took care of our every needs.
As first timers to a bike tour we were really impressed with the whole experience Great Explorations provided in our trip to Puglia.
Bike was just like mine at home. I was very comfortable with it and it was in very good shape…I felt very spoiled every night at dinner. We ate like royalty!
The guides were wonderful and definitely made the trip a delight. The food was great, but sometimes too much. Also thanks for getting us great weather-I’m sure that was part of the package!
I was blown away with everything!! The scenery, most of the accommodation, the organization, and above all the guides – Silvia and Gabrielle were absolutely remarkable!!!
Trip was fantastic, we were a family of 8 including a 8 month baby. The trip was very organized and geared to our
family. It was evident a lot of planning went into this trip to make it special and we really appreciated the attention to
all the details that made it memorable for all of us.
“The area is beautiful as a whole. The biking was enjoyable and the final three hotels were as advertised “luxe”. We really enjoyed walking around the cities. Ostuni was great in being able to stay in the city and walk at night. The second Masseria was very nice. Food was very good and plentiful. Biking in the country side of Puglia was fantastic and trips to Alberobello and ostuni were fabulous. Nice balance on the tours. Guide (Petro) was excellent during museum, Alberobello and Olive Oil factory visit. Monopoli is a fun old city to walk around for a few hours.”
“Beautiful region of Italy. Lovely to explore… especially on a bike. I had an amazing time, with a wonderful group of people in what I think is a spectacular region of Italy. The ride up the escarpment towards Alberobello and the last day ride from Otranto were especially beautiful. My favourite activities were the cooking class at the Lonardo Trulli Resort and the Olive oil tour and tasting. All the dinners were fantastic!! I thought the rides were great. I used an ebike and it was a great option… I loved it! I enjoyed the cycling and felt very proud that I did it. I was a trip I will never forget.”
“Wonderful guided tour through a beautiful region. Well organized and well executed. Guides were very informative and read the group well. Each of the hotels were well located and each offered different their own unique experiences. Dinner locations and menus were great. Vehicle support was great.”
“The whole experience was awesome! We loved our guides, the accommodation and food. The olive oil factory tour and tasting were great. We also enjoyed our cooking class. All the hotels were terrific. Our Travel Advisor was excellent! Viva Italia!”
“Great little hilltop towns. Olive oil factory and cooking class were great. As usual, loved the hotels and food. Our Travel Advisor was great – very detail oriented and quick to respond to my questions.”
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