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 in Italy. 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 7 days later in Otranto you’ll see the best of this region, all the while enjoying distinctive lodging and exquisite meals. Buon appetito!

Only Great Explorations:

  • Small groups, extraordinary guides, and authentic experiences
  • A ride you will never forget: from Otranto south along the coast to Santa Cesaria Terme
  • Cooking course with an Italian chef at a local trattoria
  • Order off the menu at restaurants you won’t find in guidebooks
  • Distinctive, charming hotels too small for larger groups
  • Wine included at first and final night receptions and at sommeliere tasting in Otranto
  • We design and operate our own trips so there are only good surprises

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 traveler who fell in love with Puglia, and stayed.




Day 1+2



Day 3



Day 4


Otranto, Province of Lecce, Italy

DAYS 5+6

What’s Included in the Cost of Your Trip?


Services of one or more experienced Great Explorations guides
Support vehicle
6 nights lodging
All breakfasts, 2 lunches, and all dinners but 1
Wine tasting in Locorontondo
Wine included at reception on first and final nights
Entrance fees for selected historical sites and museums
Detailed map and route instructions
All baggage transportation
Gratuities for all meals, hotels etc. are included; tips for Great Explorations guide(s) are additional and at your discretion

Not Included

Bike rental




Apr 3-9
Apr 29-May 5
May 13-19
Aug 29-Sep 4
Sep 7-13
Sep 14-20
Sep 16-22 - Full
Sep 23-29 - Full


Dates available upon request

Trip can start at any date. Custom trips also available. Call or email us for details.


4-16 participants


7 days / 6 nights


Monopoli / Lecce


30-65 km / 20-40+miles daily
Van supported


2 days are flat; 2 days are gently rolling; 2 days are moderately rolling


Land Cost:
US $2,950
Includes 6B/2L/5D

Single Supplement:
US $750

Bike Rental:
US $280

E-Bike Rental:
US $480

Please note: Final itinerary is subject to revision; any changes made are done so in an attempt to provide the best possible trip given route conditions and available services. Due to the nature of our business and exchange rates, prices are subject to change. All prices quoted are U.S. dollars but we gladly accept payment in Canadian dollars also. Due to cancellations and waiting lists, trip availability fluctuates daily. If you have any questions or would like to confirm space on this trip before making your reservation, please contact us at or by telephone at 604.730.1247.

Getting there
Monopoli/Egnazia: We’ll meet at 2:00 at our first hotel, the Masseria Donnaloia, located 10 km from Monopoli near the beach at Capitolo. Taxis are available from the Monopoli train station to shuttle you there.  If you are flying into Bari, and prefer a shuttle direct from the airport, cost is approximately 60 euros.


Day 1


We’ll meet at our first hotel at 2:00, where our guides will do bike fit. Let’s go cycling! The ride on this day is a loop to Egnazia, a Roman port city dating 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 about this fascinating history. We stay at the Masseria Donnaloia, a hotel located just 200 m from the beach. The hotel has a fine restaurant, swimming pool, and private beach club. We’ll host a welcome wine reception followed by dinner in the dining room of the hotel tonight.
Ride Distance: 23 km/ 40 km


Day 2


Today we’ll ride to Monopoli which boasts a charming historical center and a vibrant port where fisherman bring in the day’s catch. Visit the impressive 16th century castle, and shops and restaurants in the center and return after lunch to the hotel to enjoy the beach. Prefer a longer ride with some moderate hills? Polignano a Mare and/or Conversano are both worth visiting with historical centers and cafes to tempt. Want to challenge yourself with a century ride? Continue to Castellana Grotte to explore its cavernous grottes. Whichever ride you choose will finish with a long descent back to Capitolo. We’ll have dinner tonight at a local restaurant that will be memorable.
Ride Distance: 40 km/ 60km/ 80 km


Day 3


We’ll cycle to the Unesco World Heritage site of Alberobello which boasts over 1500 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 walk 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 whites produced here are very popular; you can sample from over 1000 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 that boasts a collection of private suites in the historical center 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 lamb chops with cheese, parsley and wild herbs.
Ride distance: 42 km or 65 km


Day 4


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 lands on quiet roads with very little traffic. Midway, we’ll have time to explore Cisternino, with great cafes and restaurants. We’ll finish the day in Ostuni, known as the “white city” with its Arab influenced architecture and a labyrinth of streets designed to confuse invaders (we’ll show you the easy way in). Tonight, we have arranged a cooking class at a local restaurant where you will enjoy eating the Apulian specialties you prepare.
Ride Distances: 36 km or 64 km


Day 5


This day will start with a transfer by local train to Squinzano and then a coastal ride with the aquamarine Adriatic at your side. The sea-side town of San Foca awaits you for lunch and afterwards we’ll continue south to historical Otranto, the most eastern point on the Italian peninsula and one of our favorite cities in the region. Like much of Puglia, Otranto had a colourful past with Greek, Byzantine, Roman, and Aragonese influences. We’ll stay at the Masseria Bandino, located just outside of town with large swimming pool and grounds. Tonight will be a free night for dinner- there are many excellent restaurants to choose between in Otranto’s center.
Ride distance: 70 km (flat)


Day 6


We save the best ride for last! Cycle south along the dramatic coastal road to Santa Cesarea Terme with unsurpassed architectural and natural beauty in one of Italy’s most serene locations. There are swimming opportunities along the way and some of the most stunning scenery in Italy. For those who want the challenge, you could continue all the way to Marina dei Leuca at the ‘southern tip of the boot’ and back for a century ride. For those who prefer to cycle directly  back to Otranto after lunch, you can explore the Castello Aragonese, a mighty fortress castle that formed the defense of the city, or relax around the pool at the hotel. We’ll finish by hosting a wine tasting with a local sommelier followed by a celebratory dinner in the dining room of the hotel.
Ride distance: 34 km, 60 km or 100 km


Day 7

Departure: We provide a shuttle to the Lecce train station by 10:00 for onward travel.

*Distance and elevation gains may vary depending on hotels chosen for specific departure.

Masseria Donnaloia , Capitolo di Monopoli

Not far out of Monopoli, in the village of Capitolo, the 5-star Masseria Donnaloia boasts outstanding views of the sea, 200 m away. It is a historic property, with an enchanting courtyard and vaulted rooms. There is a spa on site, swimming pool, excellent restaurant, and beach club nearby that guests can utilize in high season.

Sotto Le Cummerse, Locorotondo

Sotto Le Cummerse is located in Locorotondo’s old town center, surrounded by traditional white houses, charming cobbled streets and ancient historic beauty.

La Terra Hotel, Ostuni

Occupying a 13th century palace, and adjacent to St. Peter’s Benedictine monastery, this family run hotel sits in the center of Ostuni and enjoys extraordinary panoramic views of the surroundings. Built with class and elegance, La Terra offers a wonderful restaurant here and a charming bar built quarried out of stone.

Masseria Bandino, Otranto

This former 17th century manor house lies amid 5 hectares of unspoilt pine forest in one of Otranto’s most beautiful valley landscapes and features a large outdoor pool, new spa in 2022 and large comfortable rooms. The surrounding area is rich in olive trees, citrus plantations, and the Salentine beaches are only a few kilometres distance.


Trip Reviews

October 26, 2023

“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.”

October 28, 2022

“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!”

October 28, 2022

“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.”

October 16, 2019

“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.”

October 9, 2019

“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.”

October 9, 2019

“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!”

October 8, 2019

“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.”

April 29, 2019

“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.”

April 22, 2019

“Italian food was fabulous. Guides were great. Hotels were very nice. We loved the scenery.”

September 24, 2017

The tour guides provided a good mix of biking, interesting sites and good food.

June 5, 2016

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.

May 30, 2015

Great trip. Nice quiet roads and lots of riding and side trip.

May 15, 2014

Puglia was beautiful, as expected. Dinners, wine tasting, tour of Trullis, and cooking class were wonderful.

October 18, 2012

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!!

October 18, 2012

This was probably the best vacation I have ever had. Well planned with interesting activities besides the biking. Well done.

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