Puglia is the new ‘in’ place to cycle in Italy. The region combines moderate cycling, quiet roads, wonderfully charming towns including the Unesco Heritage Site of Alberobello, food and wine that is drawing rave reviews from food lovers and last but not least, exquisite hotels. Beginning in Monopoli and finishing 9 days later in Lecce you’ll see the best of this region, all the while enjoying distinctive lodging and exquisite meals. Buon appetito!
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 center like Monopoli. Additionally, masserias often feature large swimming pools and other amenities that city center hotels typically don’t offer. The main drawback is that if you wish to dine outside the hotel, you may need to arrange a taxi or shuttle, but the hotel can assist with this, allowing you to enjoy dining at your preferred location instead of being limited to the hotel restaurant.
Straight Talk
Monopoli, Metropolitan City of Bari, Italy
Day 1+2
Locorotondo, Metropolitan City of Bari, Italy
Day 3+4
Ostuni, BR, Italy
Day 5
Otranto, Province of Lecce, Italy
Day 6+7
Lecce, Lecce, Province of Lecce, Italy
Day 8+9
| Start any date between Mar 1 and Nov 30. |
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| Custom trips are also available and can start any date, call or email for details. |
Total Days
Arrive/Depart
Activity LevelModerate
Terrain2 days are flat; 3 days are gently rolling; 3 days are moderately rolling
CostClassic Accommodation: US $3,275
Single Supplement: US $820
Luxe Accommodation: US $3,975
Single Supplement: US $1,000
Bike Rentals
Hybrid Bikes: US $440
Racing Bikes: US $540
E-Bikes*: US $640
*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
Your trip starts in Monopoli. If you stay in Bari the night before the trip begins, you can take a train from Bari Centrale station to Monopoli (25 minutes). Taking the train to Monopoli from Rome, Milan or Florence
From Rome: There are several daily departures from Rome’s Termini station to Monopoli. We recommend arriving in Bari or Monopoli a day early, but if you choose to leave Rome on the day the trip begins, you could take a train from Rome’s Termini station around 7:30 am arrives in Monopoli just before 1 p.m. and we’ll arrange for the Area Manager to meet you on arrival.
From Milan or Florence: Train travel from Milan or Florence is also an option, but it is a long trip. Average travel time from Milan to Monopoli is 9 ½ hours; average travel time from Florence to Monopoli is 8 hours. There is one overnight train from Florence to Monopoli, arriving in the early morning, but otherwise to travel from either of these destinations, you need to plan on arriving in Monopoli the day before the trip starts.
Monopoli
The meeting time is usually at 1 pm at the first hotel, allowing you time to arrive from Rome by train that morning. Our Area Manager will help with your bike fit and answer any questions you may have. The ride on this day 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 can still be found. Back in Monopoli, there are many tempting restaurants to choose from.
Ride Distance: 19 km; elevation gain: 53 m or 11 km; elevation gain: 26 m
Monopoli
Today’s ride along the Adriatic brings you to the vibrant fishing village of Polignano a Mare and its impressive swimming lagoon. Here, white-washed buildings built out of the limestone cliffs sweep around the winding streets adorned with flowers and plants. Enjoy a swim in the cobalt waters of the lagoon, an espresso in one of the chic cafés or simply wander the cobbled and winding streets before continuing on to Conversano for lunch. You’ll have an option to return directly back to Capitolo or take a longer route via Castellana Grotte for an exploration of massive underground caves.
Ride Distance: 7 km; elevation gain: 10 m or 14 km; elevation gain: 10 m or 58 km; elevation gain: 480 m
Locorotondo
Today’s ride is spectacular. You’ll cycle inland to the UNESCO World Heritage Site of Alberobello with its 1,500 trulli. These distinctive round stone buildings with conical slate roofs are traditional Apulian storehouses made popular in the 19th Century by agricultural labourers. They make for incredibly scenic landscapes. The short riding option today will take you directly to Locorotondo, with more trulli en route. The longer riding option will take in the Bosco delle Pianelle Nature Reserve. Either way, we recommend allowing time for a wine tasting in Locorotondo before dinner, this region is well-known for its white DOC wines.
Ride Distance: 35 km; elevation gain: 657 m or 42 km; elevation gain: 236 m
Locorotondo
On your second day here there is a wonderful ride to the seaside town of Grottaglie or a shorter option that will have you back early for further exploration of Locorotondo. This circular city is considered one of the most beautiful in Italy and with its whitewashed maze of houses stretching down narrow cobbled streets and its beautiful historic centre, it’s easy to see why.
Ride Distance: 34 km; elevation gain: 330 m or 28 km; elevation gain: 363 m
Ostuni
Start your day cycling to Martina Franca, a small ancient hilltop town with stone walls, stunning piazzas, and tiny winding streets. Today, you’ll pass through olive groves, vineyards, and forested lands on a road with very little traffic. Enjoy a picnic in Cisternino or sample one of the specialties of this city, the bombettes, a type of roasted meatball. Your destination of Ostuni is one of the most beautiful on this trip – though that distinction is tough to label on any one place. Known as the “White City” Ostuni has a rich Arabian-influenced architecture, a labyrinth of streets designed to confuse the most adept invaders and evocative corners that pull you through archways and white-walled alleys. Tonight, we’ve arranged a cooking class at a local trattoria, where you’ll enjoy Apulian specialties you prepare with your own hands.
Ride Distance: 34 km; elevation gain: 382 m or 43 km; elevation gain: 399 m
Otranto
This day will start with a transfer by local train to Squinzano for a coastal ride with the aquamarine Adriatic at your side. The seaside town of San Foca awaits you for lunch (we recommend a gelato here) and afterwards you’ll continue south to historical Otranto, the most eastern point on the Italian peninsula.
Ride Distance: 70 km; elevation gain: 240 m
Otranto
This may be one of the most beautiful rides. You’ll ride along a rugged and rocky coastline dotted with pine forests and barren farmlands, blessed with turquoise waters and draped with bronzing bodies. The Italians love this place and flock to its shores in droves.
For those who want the challenge, we’ve included a century ride option all the way to Leuca and its famous lighthouse. Both options will take you to Santa Cesarea Terme. This town is popular for its natural hot springs and subsequent healing properties.
Ride Distance: 35 km; elevation gain: 238 m or 77 km; elevation gain: 1,278 m
Lecce
You’ll ride into Lecce today, taking a route through quiet and simply beautiful countryside. Often referred to as “The Florence of the South’, Lecce is laden with fine Baroque architecture, is an important olive oil and wine centre, and enjoys a long history of Greek traditions. We think it’s best visited on foot so we’ve arranged a tour with a local guide to show you the sites this afternoon.
Ride Distance: 47 km; elevation gain: 188 m
Depart
After breakfast, depart at your leisure — be sure to spend a final few moments enjoying the delights of Lecce before catching the train to your next destination.
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.
*Luxe Accommodation
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 in 5 ha of park and features an outdoor pool and large comfortable rooms. The surrounding area is rich in olive trees, citrus plantations, and the Salentine beaches are only a few kilometres distance.
This beautifully restored historic house, located in the heart of Lecce, offers stunning views of the iconic bell tower of Lecce Cathedral. With antique and local-style furnishings, the rooms reflect the warm, vibrant colors of the Salento region, offering guests a charming blend of history and comfort.
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.
Optional upgrade: Masseria Torre Coccaro or La Peschiera (supplement)
This boutique hotel, just 3 km outside of Locorotondo, boasts six original trulli from the 18th century and a villa built in 1900. The resort boasts a large swimming pool, charming restaurant and lovely setting.
“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.
Optional upgrade: La Sommita Relais & Chateaux (supplement)
Located just outside Otranto, this luxurious property was built in 1878, originally as a monastery. Lovingly restored with attention to its historical significance and surrounded by orchards, this is a truly wonderful hotel. It also has a large pool, great restaurant, and relaxing spa.
Set in the heart of Lecce, this elegant hotel blends historic charm with refined comfort. Housed in a restored 18th-century palazzo, you’ll find stylish rooms and timeless details. With its central location overlooking the Basilica of Santa Croce, Patria Palace offers guests an authentic taste of Lecce’s history, culture, and atmosphere.
Tour Reviews
“Very pleased with the accommodation!! Wonderful location and high standards. We loved the destination, perfect choice of town and cities, would not have changed a thing. We had the trip of a lifetime! It was the perfect mixture of natural beauty, culture, food, exercise and elegance. We are counting down the days until our next summer with Randonnee!”
“This is the third time we have taken a trip with Randonnee, and you do a great job! The cooking class was great. I went in thinking I wouldn’t enjoy it but we got to know the instructor and the cook and everyone was wonderful, a real highlight. Enjoyed the tour in Lecce. Everything worked out great. Randonnee did a great job.”
“Your accommodations are consistently not just excellent, but charming and representative of the local area as well. We had very high expectations and yet you managed to exceed them.”
“The area manager is a lovely, responsible person who tried her best to accommodate us at all times. We were truly impressed with the Puglia area and did not expect it to be so wonderful.”
“I would like to thank the Randonnee Team and specifically our Travel Advisor and the Area Manager, the local rep in Italy. Both were extremely helpful. We have worked with our Travel Advisor before and appreciated her attention to detail, responsiveness and willingness to accommodate special requests. The luxury option coupled with the challenging biking options as well as your customer service are the 3 key drivers why we have chosen Randonnee repeatedly.”
“We enjoyed Puglia none the less – what a great place for biking – hardly any traffic on the roads and the drivers are very respectful of bikes. Thanks again for your help and especially for arranging the transfer to allow us to ride down to the “tip” – that was the best ride of the entire trip!”
“The accommodations were all great, as was the cooking class. The area was beautiful.”
“The food, wine and accommodations were excellent. People were friendly. Trulli and olive groves were very interesting. Enjoyed the tour of Lecce and the cooking class in Lecce was superb!”
“Fantastic trip thru the olive groves and farmland and along the coastline of the Adriatic Sea. Food and wine were amazing. Hotels were stunning and the staff amazing. Cooking class in Ostuni was so wonderful. Can’t say enough about Randonnee. We have taken many trips with them and we have never been disappointed!”
“The towns were gorgeous and the Trulli never failed to delight! I loved my bike. Our Area Manager was fabulously gracious and attentive. I made a big difference to know we could consult her and she was always responsive.”
“We really enjoyed the quiet side of life in the country. People were incredibly friendly and helpful. I like the material you provide – enough to read in advance without being overwhelming. Our Area Manger was great and kept in constant contact to make sure everything was going fine. Cycling beside the Adriatic has been a dream of mine for some time and now it has been realized!”
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