









Italy: Puglia
Average customer rating 4.7 / 5(14 verified reviews)
This self-guided, ten-night cycling holiday explores Italyโs beautiful, sun-drenched Puglia region with its vibrant fishing villages, sandy beaches and beautiful, rolling hills, all above the mesmerising blue of the Adriatic Sea.
Cube, Nature Trekking or equivalent. Your bike hire is included in the price of your holiday and comes equipped with the relevant essentials, plus rear pannier and phone holder.
Our air prices include standard flights and transfers.


Arrive at your hotel for a welcome briefing. Thereโs time to discover the historic town of Conversano befroe choosing one of the many restaurants for dinner (payable locally).
You stay at Relais Corte Altavilla

Conversano
The 4-star hotel Corte Altavilla Relais & Charme is located right in the historic centre of Conversano, just off one of the main squares โ Piazza Conciliazione. The hotel is in an old medieval building with inner courtyard that once served as an old medieval courthouse for the town.
Following major renovation works in 2002 the hotel opened as an elegant four-star boutique hotel with 32 elegant rooms and appartments, each with its own personality and charm, with white stone walls, wrought iron furnishings, wooden-beams and vaulted ceilings.
All rooms are equipped with modern amenities including: air-conditioning, satellite-TV, direct-dial telephone, safe, Internet and mini-bar/fridge.
Local tourist tax not included (pay hotel locally)

Todayโs pedalling takes you through the rolling hills of the Valle dโItria where the air is perfumed with wild mint and herbs. Stop off in the little towns of Putignano and Noci, and view their characteristic whitewashed houses and narrow alleyways. Itโs then off to unique Alberobello and its plethora of trulli houses, the architectural symbol of the region. On arrival youโll be met by one of the staff, who will show you to your own private trullo house.
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You stay at Trullidea

Alberobello
A unique and authentic experience staying in a trulli, a traditional 15th century Apulian stone building with conical roof.
Each trulli house is made up of a double bedroom, small bathroom with shower and living area with sofa and small kitchenette.
The trullis are located in the centre of historic Alberobello, a UNESCO world heritage site, within walking distance of cafes, restaurants and shops.

Explore the narrow streets and kitsch souvenir shops, or visit the Museo del Territorio. Alternatively, cycle into the Itria Valley to visit stunning Locorotondo, with its panoramic views across the valley. Continue on to Martina Franca, with its beautiful Baroque architechture and stunning palazzi.
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You stay at Trullidea

Alberobello
A unique and authentic experience staying in a trulli, a traditional 15th century Apulian stone building with conical roof.
Each trulli house is made up of a double bedroom, small bathroom with shower and living area with sofa and small kitchenette.
The trullis are located in the centre of historic Alberobello, a UNESCO world heritage site, within walking distance of cafes, restaurants and shops.

Youโll spend this morning cycling along beautiful undulating country lanes lined with weathered stone walls, before enjoying a long downhill run with panoramic views of the Adriatic coastline and the lower fertile plains. This incredible descent will bring you down towards Capitolo and finishes through a patchwork of almond orchards, olive groves, vineyards and gloriously coloured fields of fresh tomatoes and peppers.
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You stay at Masseria San Martino

Pezze di Greco
Masseria San Martino is a restored manor dating back to the 17th Century. It is surrounded by olive groves. The rooms have a rustic traditional style and are equipped with all comforts. These rooms were once the living spaces of the Masseria where farmers used to live. Rooms have been remodeled and refurnished in perfect Mediterranean style, maintaining the original features.

Relax by the hotelโs pool, or cycle to the nearby beach. For the more energetic, ride to charming Ostuni whose whitewashed houses are neatly piled on hills rich in olive groves and vineyards.
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You stay at Masseria San Martino

Pezze di Greco
Masseria San Martino is a restored manor dating back to the 17th Century. It is surrounded by olive groves. The rooms have a rustic traditional style and are equipped with all comforts. These rooms were once the living spaces of the Masseria where farmers used to live. Rooms have been remodeled and refurnished in perfect Mediterranean style, maintaining the original features.

This morning you leave the masseria and head back to the Adriatic coast on a gentle flat route. You will cycle past the colourful fishing village of Savelletri, a perfect stop for an authentic Italian espresso or to indulge in a delicious seafood lunch. Your ride will continue past the archaeological site of Egnazia, once the location of a Greco-Roman town, dating as far back as 4BC. You then return to the picturesque coastal town of Monopoli and the 4-star Albergo Diffuso in time for a stroll before choosing your evening restaurant from one of the many eateries in the heart of the old town.
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You stay at Albergo Diffuso Monopoli

Monopoli
This property is 3 minutes walk from the beach. Set in various locations around the historical centre, just a stroll from Monopoliโs seafront and its beautiful beaches, Albergo Diffuso Monopoli offers elegant, air-conditioned rooms.
Accommodation has exposed Tuffo-stone walls and quality furniture. There is free WiFi, flat screen TV, air conditioning and a private bathroom with bath or shower.
Breakfast in the hotelโs central cafe and dinner will be in a good local restaurant.
Local tourist tax not included (pay hotel locally)

Todayโs route takes you along the stunning coastline all the way to the beautiful Polignano a Mare. Take the time to explore this vibrant fishing village before continuing to the picturesque village of San Vito with its multi-coloured boats. Head back to Monopoli and enjoy an aperitivo in the old townโs square watching the world walk past.
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You stay at Albergo Diffuso Monopoli

Monopoli
This property is 3 minutes walk from the beach. Set in various locations around the historical centre, just a stroll from Monopoliโs seafront and its beautiful beaches, Albergo Diffuso Monopoli offers elegant, air-conditioned rooms.
Accommodation has exposed Tuffo-stone walls and quality furniture. There is free WiFi, flat screen TV, air conditioning and a private bathroom with bath or shower.
Breakfast in the hotelโs central cafe and dinner will be in a good local restaurant.
Local tourist tax not included (pay hotel locally)

We transfer you and your bike to Acaya, from where youโll cycle along the stunning Salento coast to Otranto, taking in ancient olive groves and fishing villages en route.
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You stay at Hotel Vittoria

Otranto
A short stroll from Otrantoโs Old Town, the contemporary Hotel Vittoria boasts some superb facilities including a sparkling outdoor swimming pool, spa with Turkish bath, sauna and gym and an elegant restaurant. The hotel also benefits from a bar and lounge area for those after dinner drinks!

A free day in Otranto today, or an optional challenging dayโs cycling which takes you up and down along the coast south and west of Otranto, where youโll see the easternmost and southernmost point of Puglia โ a spectacular sight! You can also visit the Castel di Salve winery on your way to Santa Maria di Leuca, which is known as De Finibus Terrae, โthe end of the earthโ, before taking a shuttle back to the hotel.
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You stay at Hotel Vittoria

Otranto
A short stroll from Otrantoโs Old Town, the contemporary Hotel Vittoria boasts some superb facilities including a sparkling outdoor swimming pool, spa with Turkish bath, sauna and gym and an elegant restaurant. The hotel also benefits from a bar and lounge area for those after dinner drinks!

Today you head to Lecce on mostly flat terrain amidst endless olive orchards and menhirs. Tonight youโll stay at the stylish Risorgimento Resort (5 star) , just a few steps from some of Lecceโs Baroque masterpieces.
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You stay at Resort Hotel Risorgimento

Lecce
Featuring a roof-top restaurant with panoramic views, the Risorgimento Resort is located in Lecceโs Baroque historic centre. It offers free WiFi throughout, large modern rooms, and a relaxing spa.
Rooms are air conditioned and come with a minibar and satellite TV. Each has a marble bathroom with bathrobes and slippers.
The attentive staff provide a continental buffet breakfast. The 3 restaurants offer both Salento flavours and classic Italian cooking. Alternatively there are plenty of good restaurants nearby. Drinks and snacks are available all day at the Janet Ross Bar.
The health club offers a Turkish bath and multisensory shower. Massage and beauty treatments are also available.The hotel doesnโt have a pool but thereโs everything else! Its even got itโs own golf course (3km away)!
Piazza SantโOronzo is just 100 yards from Risorgimento Resort . The Cathedral is a 5-minute walk away.

Please note: This tour has been given a 1 Bike + rating based on ascents/descents and distance; the cycling may feel harder over the hotter months.
16.0
Kg COโe
per person, per night
Relative to other Headwater trips
We measure emissions from the parts of the holiday we organise โ including accommodation, in-trip transport, meals and activities โ and express them as COโe per person, per night. Our label doesnโt include your travel to and from the start of the trip. As a Certified B Corp, Headwater is committed to reducing this figure and to positively impacting local communities, the local environment and our staff. Learn more