Contrasts of Puglia Cycling

From $1704 per person

****# Based on 72 customer reviews
  • 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

What's included?

  • 7 nights, hotel-to-hotel
  • Departs Selected Mons, Weds & Sats from 20 Mar '17 to 14 Oct '17
  • All continental breakfasts and 3 evening meals included
  • Managed by Headwater appointed agent
  • Sustainability rating: 86%
  • Route notes and maps provided
  • High quality bikes provided
  • Optional electric bikes
  • Luggage transfers between hotels

Excellent for...

Contrasts of Puglia Cycling

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 4-star 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 hotel's atmospheric 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 Mimmo, or one of his 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 to 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.

For a longer tour, why not consider combining this with our Walks in Puglia and Matera

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)

Palazzo Indelli, Monopoli

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.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Shops
  • Market
  • Banking / cheques cashed
  • ATM / Cash machine
  • Mastercard accepted
  • American Express accepted
  • Hairdryer
  • Wifi hotspot
  • Television
  • Minibar
  • Air conditioning
  • Safe

Relais Corte Altavilla, Conversano   (4 Star)

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 - 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.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Shops
  • Market
  • Banking / cheques cashed
  • ATM / Cash machine
  • Mastercard accepted
  • Hairdryer
  • Wifi hotspot

Trulli e Puglia, Alberobello   (3 Acorn)

Trulli e Puglia, Alberobello

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.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Shops
  • Market
  • Banking / cheques cashed
  • ATM / Cash machine
  • Mastercard accepted
  • American Express accepted
  • Hairdryer

Masseria Salamina, Pezze di Greco   (4 Star)

Masseria Salamina, Pezze di Greco

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.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Mastercard accepted
  • American Express accepted
  • Swimming pool
  • Hairdryer
  • Wifi hotspot

Nearby facilities:

  • Shops
  • Market
  • Banking / cheques cashed
  • ATM / Cash machine

Travel options

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 to arrange connecting flights.

Customer reviews

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.

Reviewed by Mr Pocknell on 25/10/2016

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 🙂

Reviewed by Dr May on 04/10/2016

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

Reviewed by Mr Napier on 02/10/2016

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.

Reviewed by Mrs Freedman on 27/09/2016

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.

Reviewed by Mr Runciman on 19/09/2016

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.

Reviewed by Mr Whitton on 28/06/2016

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

Reviewed by Mr Brooks on 27/06/2016

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

Reviewed by Mr Rodgers on 02/06/2016

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.

Reviewed by Mr Jaffe on 26/05/2016

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 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.

Reviewed by Mrs Roundtree on 13/05/2016

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.

Reviewed by Mrs Brewster on 16/04/2016

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 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!

Reviewed by Mr May on 01/11/2015

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

Reviewed by Mr Procter on 16/10/2015

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.

Reviewed by Mrs Harbottle on 11/10/2015

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 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.

Reviewed by Mr Payne on 04/10/2015

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.

Reviewed by Mr Johnston on 03/10/2015

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

Reviewed by Dr Cullen on 25/09/2015

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

Reviewed by Mr McGinn on 23/09/2015

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

Reviewed by Dr Ruscoe on 22/09/2015

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

Reviewed by Mr MacMillan on 20/09/2015

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

Reviewed by Mr Hancock on 17/09/2015

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.

Reviewed by Mr Brooks on 16/09/2015

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 .

Reviewed by Mrs Mollett on 23/06/2015

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 town 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.

Reviewed by Mr Quinn on 21/06/2015

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.

Reviewed by Mr Price on 15/06/2015

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

Reviewed by Mr Day on 08/06/2015

Well organised , enjoyable and healthy

Reviewed by Mrs Phillips on 31/05/2015

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 was 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.

Reviewed by Mr Lewis on 27/05/2015

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

Reviewed by Mr Watt on 16/05/2015

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.

Reviewed by Mrs Greenwood on 14/05/2015

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. 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 !

Reviewed by Dr Padfield on 12/05/2015

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

Reviewed by Mr Jones on 12/05/2015

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

Reviewed by Ms Gillespie on 12/05/2015

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 experience 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

Reviewed by Mrs Shann on 08/05/2015

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. This 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.

Reviewed by Mr Carson on 07/05/2015

Good with one serious caveat below

Reviewed by Dr Goldberg on 23/04/2015

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 all 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.

Reviewed by Mr Trivedi on 17/04/2015

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.

Reviewed by Mr Dick on 21/10/2014

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

Reviewed by Mr Joslin on 14/10/2014

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 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.

Reviewed by Mr Smillie on 03/10/2014

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.

Reviewed by Dr Dewar on 23/09/2014

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 staff. 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.

Reviewed by Mrs Martin on 23/09/2014

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 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.

Reviewed by Mrs Elmer on 15/09/2014

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!!

Reviewed by Mrs Watts on 13/09/2014

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 headwater 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.

Reviewed by Mr Valdes on 24/06/2014

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.

Reviewed by Mrs Alexander on 17/06/2014

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

Reviewed by Mr Griffiths on 03/06/2014

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.

Reviewed by Mr Previte on 13/05/2014

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 visiting 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.

Reviewed by Mr Woolstone on 22/04/2014

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

Reviewed by Mr Dear on 17/04/2014

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 booking 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!

Reviewed by Mr Whittaker on 03/11/2013

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.

Reviewed by Mrs Marshall on 14/10/2013

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

Reviewed by Mr Morgan on 09/10/2013

Great combination of exercise, exploration and recreation.

Reviewed by Mr Emms on 02/10/2013

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

Reviewed by Mr Collins on 01/10/2013

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. 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.

Reviewed by Mr Brown on 25/09/2013

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.

Reviewed by Mr Lane-Ryan on 17/09/2013

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 it 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!

Reviewed by Mrs Mowll on 14/09/2013

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!

Reviewed by Mr Hinds on 16/06/2013

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 !!!

Reviewed by Mr Isles on 27/05/2013

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.

Reviewed by Mr Hollander on 07/05/2013

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.

Reviewed by Mr Townsend on 30/10/2012

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.

Reviewed by Mrs Sym on 30/10/2012

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

Reviewed by Mr Bayly on 30/10/2012

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

Reviewed by Mr Thomas on 17/10/2012

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.

Reviewed by Mrs Webb on 24/09/2012

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 industrial 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.

Reviewed by Ms Heard on 24/09/2012

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.

Reviewed by Mrs McIlhinney on 23/07/2012

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

Reviewed by Mr Parmenter on 16/06/2012

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

Reviewed by Mrs Hornsby on 25/05/2012

Very enjoyable despite the appalling weather.

Reviewed by Mrs Baylies on 09/05/2012

Thoroughly enjoyable!

Reviewed by Ms Beesley on 09/05/2012

Please refer to email to follow

Departure dates & prices

October 2016 departuresTour only 
Oct 3$1783
Oct 5$1783
Oct 8$1729
Oct 10$1729
Oct 12$1729
Oct 15$1729
March 2017 departuresTour only 
Mar 22$1704
Mar 25$1704
Mar 27$1704
Mar 29$1704
April 2017 departuresTour only 
Apr 1$1704
Apr 3$1704
Apr 5$1704
Apr 8$1704
Apr 10$1704
Apr 12$1704
Apr 15$1704
Apr 17$1747
Apr 19$1747
Apr 22$1747
Apr 24$1747
Apr 26$1747
Apr 29$1747
May 2017 departuresTour only 
May 1$1747
May 3$1811
May 6$1811
May 8$1811
May 10$1811
May 13$1921
May 15$1921
May 17$1921
May 20$1921
May 22$1921
May 24$1921
May 27$1921
May 29$1921
May 31$1921
June 2017 departuresTour only 
Jun 3$1921
Jun 5$1921
Jun 7$1921
Jun 10$1921
Jun 12$1921
Jun 14$1921
Jun 17$1921
August 2017 departuresTour only 
Aug 26$1921
Aug 28$1921
Aug 30$1921
September 2017 departuresTour only 
Sep 2$1921
Sep 4$1921
Sep 6$1921
Sep 9$1921
Sep 11$1921
Sep 13$1921
Sep 16$1921
Sep 18$1811
Sep 20$1811
Sep 23$1811
Sep 25$1811
Sep 27$1811
Sep 30$1811
October 2017 departuresTour only 
Oct 2$1747
Oct 4$1747
Oct 7$1704
Oct 9$1704
Oct 11$1704
Oct 14$1704

Holiday details

Holiday type

Self-guided cycling, hotel-to-hotel. Managed by Headwater appointed agent.


Selected Mons, Weds & Sats from 20 Mar '17 to 14 Oct '17, for 8 days (7 nights). We are able to offer non standard departures for this holiday. Please call for details.


All continental breakfasts and 3 evening meals included.

Other details

Please see our Planning your holiday and What's included in the price? pages for additional information. Please call us for single room supplements, room upgrade options and child prices.

Starting your tour

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.

Enquire about this holiday

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 additional information.

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We can call you when it's most convenient for you, or contact you by email if you'd prefer. Morning calls will be between 9:00-13:00, afternoon calls between 13:00-17:00, and evening calls after 17:00.
Let us know any queries you might have about departure dates, similar holidays or tailor-made options.


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  • Relaxed activity holidays since 1985

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