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Contrasts of Puglia Cycling

Contrasts of Puglia Cycling

Contrasts of Puglia Cycling

  • Beautifully unspoilt region, full of contrasts and interest-packed cycling
  • Historic wine towns, colourful fishing villages, white sandy beaches, ancient olive orchards, tiny farming hamlets unchanged over the years
  • Hand-picked hotels including two nights in a unique trullo house in UNESCO Alberobello
  • Traditional Mediterranean cuisine and excellent wines
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From $1704
  • Holiday details
  • Departs selected Mon's, Wed's & Sat's from 1 Apr '17 to 14 Oct '17
  • All continental breakfasts and 3 evening meals included
  • Managed by Headwater appointed agent
  • Sustainability rating: 86%
  • GPS route navigation provided
  • High quality bikes provided
  • Optional electric bikes
  • Luggage transfers between hotels

We're here to help

If you've any questions about this holiday call to our sales team on 1-800-567-6286 , or email sales@headwater.com

An outright winner from the start, this self-guided seven night cycling holiday explores a sun-soaked region of empty beaches, unspoilt villages and low fertile hills rolling down into the clear emerald seas of the Adriatic.

Firmly tucked away 'on the heel of Italy's boot', Puglia offers extraordinary variety and beauty with a dramatically rugged coast, providing a total contrast to the lush green interior. Your holiday starts and ends in the historic town of Monopoli. From here you pedal north up the coast, passing hidden coves and gold sand beaches where you have the chance to eat lunch in colourful fishing villages before heading inland. Here, you'll be intoxicated by the rich colours of the landscape, olive groves, fruit orchards, vineyards and ruby-red fields, all intensified by the wonderful limpid light of the Adriatic. Highlights include staying in unique Alberobello, a UNESCO World Heritage Site, and visiting the postcard-pretty white village of Ostuni as you wind your way back towards the sea.

Your accommodation is as varied as the landscape, with each place specially chosen for its unique charm and character. In Monopoli, you stay in a stunning hotel right in the historic centre of town; in Conversano, your beautiful C12 former court house, with barrel-vaulted ceilings, is just a stone's throw from the elegant Romanesque cathedral; in Alberobello, you cannot fail to be seduced by the authentic trullo houses (limestone dwellings with conical roofs that are the architectural symbol of Puglia), and, in Pezze di Greco, you spend two nights in a beautifully restored C17 masseria (fortified farmhouse) with lovely pool, open courtyard and 200 hectares of ancient palms and olive trees.

Day-by-day itinerary

Day 1 - Arrive at Monopoli

Arrive at your hotel for a welcome briefing. There's time to discover the historic town of Monopoli before dinner in the restaurant.

Day 2 - Monopoli to Conversano 27km/17mi or 55km/34.5mi

A charming route takes you along the stunning coastline from Monopoli before heading inland to Conversano. En route take time to visit the small, but vibrant fishing village of Polignano a Mare, idyllically perched on the side of the rocky limestone cliffs. Continue through the quaint, picturesque village of San Vito, with its multi-coloured boats moored up in the tiny port, before finishing your journey in the sleepy, beautiful little town of Conversano.

Day 3 - Conversano to Alberobello 39km/24.5mi

Today's pedalling takes you through the rolling hills of the Valle d'Itria 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. It's then off to unique Alberobello and its plethora of trulli houses, the architectural symbol of the region. On arrival you'll be met by one of the staff, who will show you to your own private trullo house.

Day 4 - At Alberobello

Spend today roaming around the historic centre, navigating your way through narrow streets, kitsch souvenir shops and tasting local delicacies. Or maybe visit the Museo del Territorio to discover the history of this unique UNESCO World Heritage Site. Alternatively, a circular cycle route (45km/28.5mi - route notes provided) takes you deep into the Itria Valley to visit stunning Locorotondo, with wonderful panoramic views across the Itria Valley. Continue on to Martina Franca, a must-see town given its marvellously intact historic centre, beautiful Baroque architecture, and stunning palazzi.

Day 5 - Alberobello to Pezze di Greco 39km/24.5mi

You'll 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.

Day 6 - At Pezze di Greco

Today you could just relax by the hotel's pool, or cycle to the nearby beach. For the more energetic, a circular cycle ride (48km/30mi - route notes provided) takes you to charming Ostuni whose whitewashed arches and houses are neatly piled like sugar cubes on hills rich in olive groves and vineyards!

Day 7 - Pezze di Greco to Monopoli 37km/23.5mi

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 C16 4-star Palazzo Indelli in time for a stroll before choosing your evening restaurant from one of the many eateries in the heart of the old town.

Day 8 - Leave Monopoli

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.

Where you stay

During your holiday you stay at the following hotels. If you'd like to extend your time at any of these or, if you'd like to enhance your stay with an upgraded room, just let us know at the time of booking. You can call our sales team on 1-800-567-6286 to discuss accommodation options.

If you'd like to keep your bikes with you for any extra nights we can arrange this for you for just £25 per adult per day. Please contact us on 1-800-567-6286 for further details.

Palazzo Indelli, Monopoli (4 Star)

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Palazzo indelli is a 4 star hotel ideally located right in the centre of Monopoli, near the harbour.

The hotel has 22 rooms all furnished in a modern, minimal and functional style with all the amenities of a 4 star accommodation.

Meals are taken in the hotel's restaurant, where you will be able to taste its Mediterranean cuisine with traditional local flavours.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Dates Superior Room Junior Suite
22/03/2017 - 14/10/2017 £30 £56

All prices shown above are valid from 24/01/2017. Prices are per person per night based on 2 sharing.

Superior rooms have got a balcony.
Junior Suites are larger rooms and have got a balcony.

Dates Single Room Double Room
22/03/2017 - 14/10/2017 £62 £122

All prices shown above are valid from 24/01/2017. Prices are per person, per night including breakfast. Bike hire is not included in the above prices.

Albergo Diffuso Monopoli, Monopoli (4 star)

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This property is 3 minutes walk from the beach. Set in various locations around the historical centre, just a stroll from Monopoli’s seafront and its beautiful beaches, Albergo Diffuso Monopoli offers elegant rooms, all air-conditioned rooms either have a terrace or balcony.

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 hotel and dinner will be in a good nearby local restaurant.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Room upgrades are not available at this hotel.

Please contact us for extra night prices.

Relais Corte Altavilla, Conversano (4 Star)

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The 4-star hotel Corte Altavilla Relais & Charme is located right in the historic centre of Conversano, just off one of the main squares - 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.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Dates Junior Suite or Top standard Room Top Junior Suite Top Suite
22/03/2017 - 14/10/2017 £18 £76 £122

All prices shown above are valid from 07/11/2016. The Junior Suite has charming furniture with a living room and panoramic view.

The Top Junior Suite and Top Suite have charming furniture with a living room, Jacuzzi and panoramic view. The Top Suite has got two rooms and therefore suitable for 4 people whether the Top Junior Suite has only got 1 double bed.

Please contact us for extra night prices.

Trulli e Puglia, Alberobello (3 Acorn)

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Whilst in Alberobello you'll have the unique opportunity to stay in your very own private trullo house. You may be asking, what exactly is a trullo? A trullo is a small, quirky, beehive-shaped stone dwelling, traditionally built without any cement or mortar and topped with a conical roof made of impermeable stone.

The trullo house that you'll stay in whilst in Alberobello will be one of eight clean and nicely furnished guest accommodations.

Each trullo house is made up of a double bedroom, small bathroom with shower and a spacious living area with a sofa and small kitchenette.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Dates Trullo Suite
22/03/2017 - 14/10/2017 £30

All prices shown above are valid from 05/01/2017. Prices are per person, per night based on 2 sharing.

The Trullo Suite is 65m2 and has a private patio, a kitchenette and tea/coffee making facilities..

Dates Double Room Single Room
22/03/2017 - 22/10/2017 £58 £114

All prices shown above are valid from 05/01/2017. Prices are per person, per night with breakfast. Bike hire is not included in the above prices.

Masseria Salamina, Pezze di Greco (4 Star)

Swimming Pool Icon Hair dryer icon NEARBY:

Masseria Salamina is a large 17C fortified farmhouse, set in 173 acres of rich agricultural farmland. The property is surrounded by orchards of secular olive trees that are up to 400 years old, used in the production of their own high quality, extra virgin, olive oil.

Inside the masseria, there's a large and welcoming restaurant where you can taste specialities of sumptuous Southern Italian cuisine, served in the suggestive atmosphere of the open-air courtyard.

The rooms here are simple yet comfortable and with all the necessary amenities and have been created out of the conversion of the masseria's outbuildings. The common areas comprise of the meeting hall, bar, lounge & TV room and the outdoor swimming pool with views reaching across to the sea.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Dates Farmhouse Suite Superior Room Junior Suite Deluxe Junior Suite
22/03/2017 - 14/10/2017 £28 £50 £60 £70

All prices shown above are valid from 05/01/2017. Please note it is also possible to upgrade to a Superior Suite for £90 per person per night.

The farm House suites are spacious and comfortable, approximately 50 m², composed of a double room, living room with single bed, wide bathroom with bathtub, and a kitchen. They are located in the south-east wing, of more recent construction (end '800 beginning of '900) but always adjacent to the Masseria, all with a wonderful view and with their own outdoor space.

The Superior Room is in the Manor wing of the Masseria, on the 1st floor, the owner's house since the 17C, it has valuable antique furniture, with marble bathroom, it has a hall and an indoor balcony with view.

The Junior Suite is in the Manor wing of the Masseria, on the 1st floor, the owner's house since the 17C, it has valuable antique furniture, with marble bathroom and Jacuzzi.

Deluxe Junior Suite is in the Manor wing of the Masseria, on the 1st floor, the owner's house since the 17C, it has valuable antique furniture, with marble bathroom, it has a hall and a private balcony with view.

The Superior Suite is in the Manor wing of the Masseria, on the 1st floor, the owner's house since the 17C, it has valuable antique furniture, a living room with fireplace and balcony, and marble bathroom with Jacuzzi and showerbox.

Dates Double Room Single Room
22/03/2017 - 14/10/2017 £60 £94

All prices shown above are valid from 05/01/2017. Prices are per person per night including breakfast. Half Board prices are available on request. Bike hire is not included in the above prices.


Transfers included from Bari airport at 11:30 Mon & Wed departures, 12:15 Sat departures and back to Bari airport at 09:10 Mon & Weds departures, 10:00 Sat departures.

Please call our sales team on 1-800-567-6286 or email info@breakaway-adventures.com to arrange connecting flights.


Everyone who goes on a Headwater holiday will be emailed a link to our post-holiday questionnaire where they can give us an honest assessment of all aspects of their holiday - everything from how quickly we answer the phone to how clean the hotels were - plus, of course, an overall rating and comments about their holiday.

Any feedback collected is posted straight to our website - totally unedited. So, for the real tales, twists and turns of our holidays, look no further than the reviews from our previous travellers.

Mr Pocknell

We have had a wonderful holiday with Headwater. Everything was well organised and thought out. We have cycled through gorgeous countryside, with great scenery and the majority on quiet country roads. Perfect as always somewhere nice to stop and have lunch on route and cheaply, eaten miles too much but then have cycled it off 🙂

Dr May

We did have a good holiday but experience could have been much better for reasons stated above and below.

Mr Napier

Mostly excellent, but disappointed there were more main roads than on previous cycling trips with Headwater.

In our opinion Alberobello should be dropped - too much of a tourist trap and not a 'Headwater' type destination.

Mrs Freedman

A healthy way to explore a new part of the world, if you want it to be! Very easy to reward oneself after a cycle with fine wine and food, but after all it is a holiday! Travelling self guided allows one to be completely flexible, but others might prefer to have a leader to avoid unnecessary cycling, should one take the wrong route.

Would certainly recommend this type of holiday for a group of friends.

Mrs Kings

Great holiday. The cycling was easy with the odd tougher bits but they were short lived. Varied scenery with coast and countryside. The notes/directions were at times diddicult to follow and really need updating because signs have fallen down or gone altogether and new roads have been built with new layouts so the notes are out of date. Monopoli is really lovely Palazzo Indelli is well situated right in the pretty main square. The rooms vary so if you are booking a standard room ask for the lar... read moreger ones at the back of the hotel because the one we were given at the end of our trip was tiny and noisy being on the side at the front. Corte Altavilla is nice too but the staff on reception were unhelpful and grumpy. I am a coeliac and despite telling them in advance it was the only hotel that did not provide anything for me at breakfast other than fruit. The restaurant in the hotel for the evening was very good. Alberobella unfortunately has rather sold its soul and is very over commercialised. The Trulli are nice but we would have preferred some outside space as they are rather dark. Masseria Salamina is fabulous we had a huge room and you really feel like you are staying in a castle. The swimming pool was lovely and we really enjoyed our stay here. Overall a thoroughly enjoyable trip and we are now looking for another one!

Mr Runciman

The holiday certainly lived up to its name: Contrasts of Puglia. We enjoyed beautiful places both in town and in country. Weather conditions ranged from bright sunshine and blue skies to thunder-storm deluges --- but with the offer of alternative transport on the wettest days. Italian food was wonderful. Overall, it was a memorable week, and we are looking forward to a next time.

Mrs North

Puglia is a fabulous area of Italy. A great variety of terrain with scenic routes.

Mr Whitton

Generally an excellent service but based on past experience will only go for future holidays with you where a Headwater rep is involved rather than an agent

Mr Brooks

Bikes excellent. Lunches en route excellent. Accommodation a bit mixed.

Mr Rodgers

No comment - the unseasonal weather curtailed cycling on one day (thunderstorms) so this did affect the overall holiday experience with another day that was also wet.

Mr Jaffe

Thoroughly enjoyable holiday in a beautiful unspoilt part of Southern Italy. The people here are incredibly friendly, not just in the hotels but everywhere. The cycling wasn't too strenuous and the 7km descent into Capitolo was exhilarating ! All the hotels were of a very good standard. Enjoyed staying in the Trulli house even though Alberobello can become very busy with day trippers but our favourite place was the Masseria Salamina, (keep some space in the luggage to stock up on their excellent... read more home produced extra virgin olive oil) ! The food in this region is wonderful with a good choice of restaurants at all the locations except Prezze di Greco where the evening meal is included. This was our 12th Headwater cycling holiday and it lived up to expectations.

Mrs Roundtree

Puglia is a fantastic part of Italy to visit - a real hidden gem - and a perfect location for cycling. We were lucky with the weather and got a good week but the weather in April can be variable (i.e. cooler and wetter than we had). Beautiful countryside and lovely coastline with proper beaches. Excellent food and friendly people, We would go back again.

Mrs Brewster

April was a beautiful time of year to travel to Puglia; lovely weather for cycling and the fields were full of wildflowers, cherry blossom, flowering mimosas etc. Although the cycling was all on roads, they were mainly very quiet, country lanes and we found the Italian drivers surprisingly patient and respectful of cyclists. The route deserved its 1 1/2 bike rating; it certainly seemed a bit more strenuous than the previous '1 bike' holiday we had done and we were very glad not to be tackling it... read more in the heat of summer. This was our second Headwater holiday as a family and we think the formula works well for both us and the children (aged 11 and 13). They particularly embraced the Italian love of gelati!

Mr May

A beautiful part of the world made even more special by great hotels, great food and great cycling

Mr Procter

We were well looked after in all aspects of the holiday, from the comprehensive introductory talk, which was both entertaining and full of useful bits of information, through the well-planned and comprehensive route notes, to the excellent accommodation and surroundings of the rides.

Mrs Harbottle

Pleasant cycling through mix of peaceful rural landscapes and historic coastal and plateau towns. Although experienced cycle tourists we found the cycling more tiring than expected due to the heat, even in early October, so were glad that the distances were relatively short. Puglian food lived up to its reputation and the local wines recommended by the rep were enjoyable. All the hotels had spacious and well equipped rooms - though we did benefit from an upgrade for the base hotel as the normal... read more one was full. Detailed route notes a great relief after getting minimal and inaccurate ones last year with another company. Unplanned highlight was doing the 7km downhill run while road closed to cars as a proper cycle race came up.! Although not mentioned in the brochure, Monopoli is well connected to the rest of Italy by train, and the station is within walking distance (20 min) of hotel. So we negotiated a reduction in package cost as not needing a transfer to Bari, and made the cycling week the centre of an Italian / French train tour.

Mr Payne

Very good holiday overall, in a very interesting area. Route notes were at times inaccurate and ambiguous, which made the ride more like a treasure hunt!

All the hotels and accommodation were of a high standard and staff very friendly and helpful. Bikes were ok but not as good as the Headwater branded ones that we had in Burgundy last year. We would strongly recommend a Headwater holiday.

Mr Johnston

Good accommodation, clear instructions and good cycling. Met interesting people. Guides were very friendly and helpful.

Dr Cullen

Really enjoyable, few small comments, maps were hard to read, water bottles ideally insulated, stands of bikes needed, lovely holiday, expensive especially because of euro/sterling exchange

Mr McGinn

This is our 7th cycling holiday with Headwater and once again we have had a really enjoyable holiday.

Dr Ruscoe

Puglia is a great destination for a cycling holiday. Hotels were welcoming, helpful and of good standard.But you definitely need better arrangements for route checking/updating and translation of self-guiding instructions, which misrepresented a number of key instructions, resuling in errors and distress. You continue to give paper instructions which don't fit the holders. Other companies provide mileometers and satnavigation

Mr MacMillan

Lovely cycling trip, local agents, hotels and bikes were very good. The Trulli hotel was interesting, but dark and lacking in facilities.

Mr Hancock

The Italians could be encouraged to look after their surroundings better .The amount of rubbish by the sides of the roads is awful .It's such a shame and detracts from the unspoilt countryside.The historic centres of the town's are really interesting and not crowded.

Mr Brooks

An Italian adventure. Excellent bikes, fabulous food. Sometimes the instructions were a challenge but generally ok. Accommodation was varied which added to the overall experience, The Masseria Salamina was exceptional. Our rep Dave was a joy .

Mrs Mollett

The welcome briefing was far too long, we expected it to last for about 15 minutes and it went for over 2 hours. We could have read the notes ourselves, rather than having the rep read them to us. The route notes were excellent and easy to follow. Puglia is a varied part of Italy, some parts are stunningly beautiful, other bits less picturesque. Alberobello has been spoilt by the number of tourists and souvenir shops, we would have preferred to stay in Locorotondo, which is a far more beautiful ... read moretown without the hoards of cruise ship tourists, although staying in a Trullo was a great experience. The people of Puglia that we came in contact with were incredibly friendly, helpful and kind, and the food and wine were amazing. All in all it was a good cycling holiday with lots to see and varied cycling.

Mr Quinn

It was our first cycling holiday - we both really enjoyed it. Just the right amount of cycling. The suggestions of what to do on the non cycling days were very helpful. Unfortunately we got lost in Potigano - maybe you should recheck the route notes for leaving the old town. One of the highlights of our holiday was a boat trip on the final day on the Yasemin Sultan.

Mr Price

A well planned and run cycle tour through a beautiful part of Italy with good accommodation.

Mr Day

Well organised , enjoyable and healthy

Mrs Phillips

Everything ran smoothly, with no problems with the transportation of luggage or airport pickup and drop off. The initial briefing by Davide was very thorough and informative. We found the route notes straightforward on the whole but there were a few inaccuracies. Hotels were of a good standard, but we were glad to have taken the option to upgrade, particularly at the Palazzo Indelli where our junior suite had a large terrace overlooking the lively piazza. Having outdoor space at the Trullo wa... read mores also beneficial. Alberobello is interesting but very touristy and on the leisure day there, we opted to take the train to nearby Martina Franca, via Locorotundo and would recommend this. Italian trains are cheap and easy to use - just don't forget to validate your ticket before boarding! The cycling generally was perfectly manageable, although there was the odd challenging climb. On the last day, we chose to go our own way and followed the coastal route back to Monopoli, rather than go inland. This gave us an enjoyable but shorter ride, allowing us to enjoy the rest of the day in Monopoli.

Mr Lewis

Very good accommodation in interesting buildings; friendly people; interesting towns; remarkable ancient olive trees; some days are very hilly.

Mr Watt

This was our 13th holiday out of 15 with Headwater and the best yet! You are ahead of your competitors that we have tried.

The location of the trip was ideal.

Mrs Greenwood

Accommodation and transfer/transport arrangements were good and enjoyed. We thought a Grading of 2 would be more appropriate ; the first two days were difficult. However the route directions were disappointing and in one place wrong. Although the directions were recently revised, I suggest they are reviewed, in particular:

Page 9: the ERG petrol station has been replaced by a building site. On the same page, the 2 electric poles are on a right turn and the Via Marascelli sign is not there... read more. The directions in and out of Noci were confusing and need clarity, probably by removing choice of routes around the town.

Page 28. Conchia to monopoli at the junction with the give way sign , it should say turn left! At present no direction is given. There were other minor errors along the whole route but as you say, signs change !

Dr Padfield

Marvellous trip. Good that you arranged no rain and temperatures of 32 degrees

Mr Jones

This experience allowed us to see the delights of Puglia at our leisure. The route took us through the most beautiful countryside and was made perfect with the excellent food, wine and accommodation

Ms Gillespie

Loved Puglia and everything about the region - scenery, cycle rides, food and especially the negro amaro wine we discovered. The accommodation was brilliant especially the Masseria although we did also really like the vibe of the main square in Monopoli.

There were just 3 slight disappointments

1. The spa at the Corte Altavilla in Conversano was all style over substance and was over-priced

2. The food at the Corte Altavilla was also slightly disappointing after our ... read moreexperience in Monopoli

3. The town and local maps provided by the local agent were utterly useless. Google was much better! They also didn't sometimes tally with the Headwater accurate directions

Mrs Shann

The cycling was more challenging than expected from the description mainly because of the many climbs involved. One of our party struggled with this, the fitter members of the party found it hard at times but more manageable

Puglia is a lovely uncommercial area of Italy and I would like to visit it again. The people are very friendly and helpful.

The bikes are very good but would benefit from the water bottles more easily accessible instead of having to be stored in the panniers. T... read morehis is not allowed because of some ridiculous health and safety rule. There is a worry that you will try and drink from your water bottle when cycling.

Mr Carson

Good with one serious caveat below

Dr Goldberg

We have just had a wonderful week cycling in Puglia with Headwater. We would highly recommend going in late April/May as the countryside was covered in wild flowers and the weather was perfect for cycling at around 18C. The bikes were just right for the routes which are all on roads. Most roads are quiet but some were busier than I was expecting especially coming into the towns but the Italian drivers were surprisingly deferential and careful around cyclists. The hotels chosen by Headwater were ... read moreall excellent. All the evening meals we had were delicious, both those provided and those we found ourselves. Not one disappointing lunch or dinner in the whole week! Some of the route instructions need clarification and personally I would have preferred them to be a bit shorter but overall an excellent weeks holiday. I'm sure we will be booking again with Headwater next year.

Mr Trivedi

We loved this holiday. Dave provided comprehensive information on the routes and accommodation at our initial briefing, and could not have been more helpful. He also gave us lots of background information to help us make the most out of our holiday. Puglia is a beautiful area ideal for cycling, and the hotels (which were all excellent) all had very different characters, which added extra interest to the holiday.

Mr Dick

Well organised holiday. Lots of places to visit and experience as a result of thoughtful planning. Good, comfortable accommodation and food.

Mr Joslin

This was our first time with Headwater and the impressive, friendly and efficient service, together with very good hotels in a variety of beautuful locations, ensured our total enjoyment. The routes suggested were good and we had the option of extending our rides (in particular an extension to the coastal ride on Day 1). A slight criticism would be that the directions could be clearer and presented in specific instructional order rather than paragraph narratives; we were not sure that anyone had... read more actually cycled these routes 'blind' and thus we made some mistakes. neverthelessall rides were completed successfully. Puglia is something of a gem and the programme ensure that we enjoyed a full flavour of its varied geography and history. We would have no hesitation in booking another of your holidays and thank you for such a pleasureable experience.

Mr Smillie

We are not regular cyclists and this was our group's (6 of us) first experience of a cycling holiday and of using Headwater.

The organisation was very good and the suggestion of Puglia for this adventure was first class.

We had excellent weather to enjoy lovely countryside and well chosen locations and accommodation.

Dr Dewar

Really excellent trip. Cycling was great and not too strenuous although cycling every day a reasonable distance. Beautiful scenery passing through coastal areas with shimmering sea and quiet coves, on to endless olive groves with not a person in sight. The Puglia towns are delightful in character. Hotels are undoubtedly excellent especially Masseria Salamina (a gem - what a location, luxurious pool area, fabulous dinners) and Trulli stay was also a delight, with very friendly but not intrusive s... read moretaff. The cycling is all on surfaced roads which means that the provided bikes were more sporty and made cycling easier (lighter frame, thinner tyres, gearing better, no mudguards or bell). Southern visions, your local partners, were really helpful - we were travelling on to Dubrovnik by ferry and the transfer driver spent quite some time locating the left luggage for us, which would have been impossible for us without good Italian. Thus was really appreciated as we were able to relax in Bari for the day. Finally the Spa in a Corte Altavilla was a great bonus - each of us had a well-earned massage from Andreas after steam room and soaking in the hot tub. Weather was excellent (iPhone weather suggests cloudy and thunder storms but neither was accurate - sunshine daily in mid to late September.

Mrs Martin

Definately worth a try and nice varied holiday. It was good to experience a different part of Italy. Whilst for us it doesn't quite match up to the scenary of home and other parts of Italy such asTuscany and Umbria, it has its own charm. Our cycling route took in a good mix of the coast, the coastal planes and the plateau and some lovely little towns. The cycle down from Alberobello was lush. As we live in God's own countyclose to the Yorkshitre Dales all the miles of dry stone walling made... read more us feel quite at home. Luckily we don't have anywhere near the problems the Italian's have with roadside litter and fly tipping. It's a real shame. However, it's not all like that by any means. It certainly isn't something in Headwater's control as isn't the weather, which was indifferent but we managed not to get wet whilst riding, which was good and we did see some sun - just thought it might have been a bit better in early September, but your in the lap of the gods . There's some fantastic old olive vines throwing up some weird and wonderful trunk shapes to feast your eyes on. We saw very few animals despite there been a plentiful array of meat on the evening meal menus. The people we met from Southern Visions your local agent were all very friendly and they provided an excellent service. Manopoli was a wonderful place to start and the Palazzo Indelli a nice little hotel right in the thick of the old historic quarter in a lovely little square, which came alive at night, and close to the waterfront with its fortifications and castle. Worth doing the extra short loop on the first day if you want a bit of fish for lunch. Corte Altavilla was a nice little hotel also and well located just off the square by the cathedral and near the castle in Conservano. I just thought the hotel restaurant on the top floor lacked a bit of atmosphere, but we were only there for one night, so no great shakes. This hotel looked to have a good spa, but it was fully booked, so if you want to partake best to book in advance. Staying in the Truli house was an experience, as were the bangs on the head I gave myself on the low doorways! However, previous reviews on your website weren't wrong that you had saved the best until last - the Masseria Salamina. I dont think I've ever felt so relaxed so quickly on arrival at a hotel and I've stayed at many. We were so pleased that after reading the other reviews we'd opted for another night. In fact if we went back and did this trip again I'd be looking to rejig things to stay in Arerobello and the Trulli House for just 1 night instead of 2 and have a further night at Masseria Salamina. What a lovely place. There's opportunities for those who want to mix cycling with a bit of train travel with the bikes, such as the round journey from Alberobello where we actually chose in the end to take the train back from Marta Franca. Be aware Italian drivers seem to like to honk their horns I guess to tell you they are coming even though you've already heard them. Overall a very pleasurable experience well worth a go.

Mrs Elmer

Puglia as a region is over-hyped. You will mainly be cycling along dusty roads through olive trees. The southern Italian towns have very messy litter strewn outskirts with disused factories and omnipresent graffiti but once you get to the centres you will find lovely old walled towns with stone pavements - completely closed as you are most likely to arrive in the middle of the afternoon siesta!

you did ask!!

Mrs Watts

We celebrated our wedding anniversary with this holiday. Overall we had a wonderful experience despite the unseasonably wet weather in Apuglia this September. We flew independently and organised ourselves 2 days in Lecce which we would recommend. We arrived in Monopoli by train and walked to the hotel - from there on we were welcomed and looked after by Southern Vision rep Davide who was extremely informative. We were a bit concerned that we would end up on a group tour but the other headwate... read morer guests were lovely and everyone had their own plans and did their own thing. The cycling was just the right level for us, the hotels great! The inclusive food was very good standard and elsewhere we did not have one course of food that was not delicious! Highlights were the pretty town squares, the Esspressini, the Vongole, the Negramero wine, the sea food at Savelletri, the afternoons lazily cycling through olive groves, the quiet routes and the friendly people of Southern Italy. When we arrived at Bari airport with the wrong passports with 50 minutes before the gate closed, Southern Vision contacted Salamina, and then the young Boss Phillipo (apologies for spelling) broke the land speed record, and every level of service and commitment to get our passports to us! while the Southern Vision team worked on a backup plan the accommodate us and rearrange flights - All in under 45 minutes! We made our flight, sweating, tired, but very happy that we had chosen Headwater for a great fun way to celebrate.

Mr Valdes

The holiday was very enjoyable and the suggested places to visit/eat and short town guides were very helpful. The food in this part of Italy was amazing and there was a lovely mix of Coast and hills.

Mrs Alexander

our third Headwater holiday. Set dinners in the hotels often poor and we are really fed up with this. It is not a cheap holiday but we seem to get the dregs of the food. Our best meals were out in independent restaurants. On the first night when Pallatzo Indelli couldn't feed us they sent us out for a wonderful simple fresh supper at a restaurant. Dinner with them the second night was DISGUSTING. We felt like the poor relations.

Headwater response:
Dear Mrs Alexander, Thank you for your constructive feedback, We were sorry to see that you were disappointed with the standard of meals served at some of the restaurants on this holiday . We have discussed your comments with our local suppliers and from this some new menus have been put into place with more choices available. Whilst the overall feedback for this holiday is positive, we realise we cannot afford to let our standard slip and thank you for bringing these points to our attention. We hope that by making these small changes our customers will continue to enjoy this lovely area of Italy. Yours sincerely, Headwater Customer Service team

Mr Griffiths

Good fun helped by good weather, hotels, food and wine.

Our stay in Monopoli was wonderful and the hotel was ideal - got a little lost on our way back on the first cycle ride as we mis-counted some of the 'Y' turns. Enjoyed the cycle rides along the side roads - pretty wild flowers in May.

Mr Previte

Because of our ages (I am 80, my wife is 78) we decided not to do the Puglia trip on bikes but by car. This worked very well. The only problem was the very narrow streets and difficulty in finding the way in Monopoli. Doing it by car meant we had more time to explore the places where we stayed and time to drive to Lecce. We thought that Masseria Salamina would be a very good base for anyone wishing to explore Puglia by car. It is a lovely hotel, easy to find and in a good location for vis... read moreiting other interesting places in that area. The sea food restaurants on the coast are excellent, especially one at La Forcatella. The remains of the Roman town and port at Egnazia and the museum are very intersting.

Mr Woolstone

A wonderfully authentic Puglian expeience -great locations, countryside, food, wine & cycling

Mr Dear

We decided to book our own direct flights with BA instead of using the advertised Alitalia via Milan flights. The timings don't differ significantly and Headwater were happy to arrange non standard transfers at no extra cost. The standard of accommodation throughout the trip was of a high standard. We really enjoyed the stay in the Trulli house and were pleasantly surprised to be given a Trulli suite with a small patio garden! The highlight however was our stay in the Masseria Salamina. On booki... read moreng we upgraded to a garden suite but on arrival we were delighted to be allocated the luxury suite complete with private balcony and sea views. We were made to feel really welcome by the family and the food was excellent. Simple, fresh and plentiful with much of it coming from their own farm.

The map of the area is only good for an overview but the route notes and briefing were excellent and at no point did we stray off route. Some of the roads (as has been mentioned before) are in a poor condition but this did not detract from the enjoyment of the cycling.

Another enjoyable, well organised and well supported holiday from Headwater. The next one is already booked!

Mr Whittaker

This area of Italy proved to be lovely for cycling. Most of the routes were along very quiet lanes lined with dry stone walls, along side olive groves and vineyards. Staying in a Trulli in Alberrobello was a delightful experience, so much so that we wish we had been able to book an extra night: we didn't cycle on the middle day as we wanted to look round the town.

Mrs Marshall

Your local agent organised a great tour through Puglia, linking key sights of interest via lovely quiet back roads where we observed rural life.

Mr Morgan

Great combination of exercise, exploration and recreation.

Mr Emms

nice hotels, gentle cycling and wonderful surroundings....all makes for an enjoyable and relaxing break

Mr Collins

On the whole all the hotels exceeded our expectations as did the bikes, which were very good, though I would recommend extra padded cycling shorts.

If you arent going to have lunch at a restaurant en route, buy your provisions early, because everything closes for lunch, we never did work out the closing times, as we always seemed to be on the road. Many of the roads are awful, so those padded shorts will serve you doubly!

The dinners are plentiful and wonderful food... read more. The routes are delightful, mainly on small roads with little traffic. There was only one day which proved to be rather taxing with a lot of ups and downs from Alberobello to Martina Franca. Luggage transportation went without any hiccups and all in all it was a really enjoyable destination to catch the last of the summer warmth.

Mr Brown

have spoken to joanne prior to your e mail but conform we thought the holiday was excellent in every respect. bikes were brilliant hotels and food better than expected. the area was fascinating and very unspoilt and great cycling routes.We were dismayed to hear of Ali accident just after our our meeting and hope she recovers quickly and fully because she was really great and helpful and knowledgeable and sensible. One set of directions per cyclist would have been better and advance warning of city taxes in two of the hotels might be wise. Otherwise a really great holiday.

Mr Lane-Ryan

Negatives first: Somewhat expensive for the type of holiday which will cause us to carefully evaluate 'rival' companies for next year. The countryside was too similar and the beaches poor unlike the Alsace tour we went on previously which was pleasantly varied with overall better hotels. The trulli experience was not to be recommended, no working air conditioning, light bulbs missing etc... On pointing this out told the air conditioning had been switched off as weather getting cooler ! In fact i... read moret could be switched on but did not work. Our friend next door discovered the air conditioning in his house had no plug. The plumber was to be told about the problem and we had a fan so clearly problem was longer standing.

Positives: the hotels were all good and staff helpful in most, the organisation of the tour by Southern Visions was excellent and the Salamina was to be particularly recommended. Weather perfect.

Overall we were happy with holiday but will be more careful over selecting the area we go to next year to ensure variety/interest. That is not the fault of Headwater!

Mrs Mowll

Headwater were friendly, efficient and the holiday was well organised throughout with comprehensive directions. Rest days offered the opportunity to put the bikes on the train for part of the tours, or just cycle part of the routes and the hotels were well placed for this and other sightseeing. All in all, a very good holiday was had by all!

Mr Hinds

SShhsh! Don't tell anyone about Puglia ! After many years of travel in Italy , We have a new favorite region ! Wonderful food and wine,peaceful rural and coastal lanes, and each town is more beautiful than the last ! A real treat of a holiday - and few tourists ! Let's keep it like that !!!

Mr Isles

This was our eighth Headwater holiday over 20 years and they have all been very enjoyable. Yet again, Headwater and their agents were very efficient throughout. We were particularly impressed by the Masseria Salamina which exceeded our expectations and was a perfect place to finish our holiday.

Mr Hollander

Puglia tourist people very welcoming and can be very helpful but be careful of gross overcharging.

Look at your bills and dispute perceived unfairness on the spot.

Mrs Sym

We enjoyed the holiday but not as much as we thought we would! We all enjoy good food sadly on this holiday we were let down we had 3 good meals out of 7

Mr Townsend

The Puglia cycling tour was well organised, and well supported by local staff. We had excellent weather in mid October wth temp 22-25 deg C. The only significant criticism (not within your control) was the appalling state of the litter at the side of many many roads especially on the coastal plains. It is not at all relaxing to be cycling through lovely countryside and regularly come face to face with the WHOLE range of domestic litter strewn along the edges of fields. For that reason alone, I would not recommend this particular trip to anyone else. This is not a reflection on Headwater.

Headwater response:
Unfortunately, there have been a couple of occasions where we have been informed of some littering on this particular tour. It is such a shame and very frustrating, as Puglia really is a beautiful region. It does not however, seem to be a continual problem and we do our utmost to avoid these areas on the routes we take. Our local agent continues to raise the matter with the local authorities, in an effort to eradicate this problem for the future. Thank you for sharing your experience with us so we can continue to monitor the situation.

Mr Bayly

Wonderful. One of our best ever holidays. Challenging and relaxing in equal measure - a fabulous break.

Mr Thomas

Poor bikes. Heavy frames and too highly geared. Skinny tyres no good on broken tarmac surfaces. Broken spoke. Puncture.

Why not mountain bikes?!

Headwater response:
We are sorry that you found the bikes to be such an issue, this is genuinely not something we have come across before in this area. We will be speaking with our local agent about your experience and can assure you that we will be monitoring future feedback closely. If we do feel that a different style bike would be beneficial, we will certainly consider making this change.

Ms Heard

Puglia is very different to Tuscany more rugged than beautiful but a lovely coast line with super sandy beaches.

A good mixture of easy and hilly cycling which we felt was accurately graded.

All the hotels had their own character but we especially enjoyed the Masseria Salamina and wish we had had an upgrade. Alberobello is very touristic and commercialised with lots of cheap souveniers but staying in a trulli was a novelty!

We especially enjoyed the company of the other Headwater cyclists.

Another successful Headwater Cycling Holiday.

Mrs Webb

It was great. Warm weather, great company with the people we met up with in the evenings (and chose to go cycling with on the final day, and lovely places to stay.

Where the notes could have been better, we have already given feedback to the people on the ground and we recognise that signs change!

Our one recomendation for change that we would give to future visitors is to take the train from Conservano to Arborobello - this would avoid cycling through the industr... read moreial wasteland of the first town visited (big lorries, lots of dust) and the rubbish in the countyside between there and Noce. It would also give time for a morning in the old town of Conservano and a 1.30 pm train onwards; a cheap and easy option. We took the following day off cycling (needed a rest and a long lunch) but have been told (via the blue book) that it was one of the best days cycling - we visited the town of Locotorando by train and it was indeed beautiful.

Other than that, we had a great time and are planning our next holiday already.

Mrs McIlhinney

We had a brilliant holiday in a part of Italy we had never visited before – with so many olive trees!

Mr Parmenter

Puglia is a wonderful area in which to cycle and we enjoyed every day of our holiday.

Mrs Hornsby

Very enjoyable despite the appalling weather.

Mrs Baylies

Thoroughly enjoyable!

Ms Beesley

Please refer to email to follow

Dates and prices

The prices quoted below for each individual departure supercede those published in our current brochures. Air prices are subject to change and are shown for guide purposes only. Please see our Planning your holiday and What's included in the price? pages for additional information.

Alternatively, you can call our sales team on 1-800-567-6286 to discuss your requirements in more detail.

You can be confident that our pricing includes all the standard requirements of your holiday and many additional extras. Always ensure that you are comparing like for like when booking your holiday. Find out about The Headwater Price Promise to ensure you're getting the very best value for money.

  • Oct
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Oct 2016 Tour only Availability
3rd Oct US$1783 Check
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8th Oct US$1729 Check
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Mar 2017 Tour only Availability
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May 2017 Tour only Availability
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Jun 2017 Tour only Availability
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Aug 2017 Tour only Availability
26th Aug US$1921 Check
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Sep 2017 Tour only Availability
2nd Sep US$1921 Check
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11th Sep US$1921 Check
13th Sep US$1921 Check
16th Sep US$1921 Check
18th Sep US$1811 Check
20th Sep US$1811 Check
23rd Sep US$1811 Check
25th Sep US$1811 Check
27th Sep US$1811 Check
30th Sep US$1811 Check
Oct 2017 Tour only Availability
2nd Oct US$1747 Check
4th Oct US$1747 Check
7th Oct US$1704 Check
9th Oct US$1704 Check
11th Oct US$1704 Check
14th Oct US$1704 Check

Holiday details

Minimum group sizes
No minimum group size, however transfers are subject to at least 2 people (in total) booked on each departure.

This holiday is unsuitable for children.

Holiday type
Self-guided cycling Managed locally by Headwater appointed agent.

selected Mon's, Wed's & Sat's from 3rd Oct 2016 to 14th Oct 2017, for 7 nights.

All continental breakfasts and 3 evening meals included

Electric bikes
It is possible to hire electric bikes for this holiday at a supplement of £125 per person. As these are available on a first come first served basis, we recommend early booking to avoid disappointment. Please call us for further details.

Other details
Airport transfers are subject to at least 2 people (in total) booked on each departure.

Tailor-made travel

Tour only
Transfers included from Bari airport at 11:30 Mon & Wed departures, 12:15 Sat departures and back to Bari airport at 09:10 Mon & Weds departures, 10:00 Sat departures.


Due to the tailor-made nature of our holidays, we need a little more information in order for us to check availability for Contrasts of Puglia Cycling. Simply complete the form below and a member of our sales team will contact you (when it's most convenient for you) to provide availability information, travel options and an accurate price. Of course there's no obligation, but if you do wish to proceed with a booking they will be on-hand to assist you throughout the process.

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