Highlights of Puglia Cycling

0044 1606 720199

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  • Holiday code
    C10PU
  • Holiday type
    Self-guided cycling
  • Duration
    10 nights
  • Accommodation
    hotel-to-hotel
    , , and
  • Activity level
  • From $3920per person, tour only
  • Departure months
    JFMAMJJASOND
  • What your holiday price includes
  • 10 nights hotel-to-hotel accommodation in a mix of , , and hotels
  • All continental breakfasts and 2 evening meals included
  • Bike fitting and briefing at the start of your holiday
  • Headwater navigation app
  • Bike hire included
  • Standard transfers at the start/end of the trip (if booking inclusive flights)
  • Luggage transfers between hotels
  • Optional Upgrades
  • Electric bikes available
  • Room upgrades and extra nights at selected hotels
  • Suitable for
  • Couples
  • Excellent choice for
  • Food lovers, wine lovers, flora & fauna, art & history, swimming opportunities, vegetarian meals, coastal routes
      from 7 reviews

Michael John Wilson-maccormack says...
Such a great way to experience a destination. The routes allow you to soak up the landscape and the culture at a leisurely pace. It actually covering ...
Read reviews »

Italy: Puglia

Highlights of Puglia Cycling

  • Sun-drenched, unspoilt region; contrasting cycling routes taking in the rugged coast and lush green countryside
  • Vibrant fishing villages, white-sand beaches, historic wine towns and ancient olive orchards
  • Stunning Salento coast - visit Otranto and Baroque Lecce
  • Hand-picked accommodation including a unique trullo house in UNESCO Alberobello
  • Excellent regional wines and Mediterranean cuisine

This self-guided, ten-night cycling holiday explores Italy's beautiful, sun-drenched Puglia region with its vibrant fishing villages, sandy beaches and beautiful, rolling hills, all above the mesmerising blue of the Adriatic Sea.

Puglia offers a wonderful contrast of landscapes, from the fertile farming hamlets, vineyards and orchards of its interior to its dramatic, rocky coastline. Your holiday starts in Conversano and heads inland where you'll be blown away by a rich landscape of vineyards, olive groves, fruit orchards and fields of tomatoes and peppers alive with colour. Marvel at the UNESCO World Heritage Site of Alberobello with its unique trulli houses - emblematic of the region - and the glistening, whitewashed village of Ostuni. After a transfer to San Cataldo you'll discover the delights of the stunning Salento coast, taking in Puglia's easternmost and southernmost point - an amazing sight - and the Baroque masterpiece that is Lecce, renowned for its stunning 18th century architecture and known as the 'Florence of the South'.

You'll stay in an excellent variety of accommodation on this holiday, including four star or five star hotels! In Conversano your elegant boutique hotel is just a short walk from the medieval streets and Romanesque cathedral of this historic town; and an authentic trullo house in Alberobello. While in Lecce you stay in the heart of the beautiful old town in sumptuous five star hotel, close to the Roman amphitheatre and Baroque palazzi, with the hotel's roof garden offering one of the best views there is over the city.



We're here to help

If you have any questions about this holiday call our sales team on 0044 1606 720199, use our live webchat or email sales@headwater.com

Cycling information

Routes are gently undulating, with the latter stages from Monopoli to Lecce being predominately flat. 95% of the routes are on tarmac. The routes generally keep to quieter, secondary roads although you should expect more traffic in the towns.




We're here to help

If you've any questions about this holiday call our sales team on 0044 1606 720199 , or email sales@headwater.com

Day 1: Arrive at Conversano

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

Day 2: Conversano to Alberobello (39km/24.2mi)

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.
You stay at the Trullidea (breakfast included)

Day 3: At Alberobello

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

Day 4: Alberobello to Pezze di Greco (49km/30.4mi)

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.
You stay at the Masseria San Martino (breakfast and evening meal)

Day 5: At Pezze di Greco

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

Day 6: Pezze di Greco to Monopoli (37km/23.0mi)

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

Day 7: At Monopoli

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

Day 8: Monopoli to Otranto (42km/26.1mi)

We transfer you and your bike to Acaya, from where you'll cycle along the stunning Salento coast to Otranto, taking in ancient olive groves and fishing villages en route.
You stay at the Hotel San Giuseppe (breakfast included)

Day 9: At Otranto

A free day in Otranto today, or an optional challenging day's cycling (55km/34.5mi) which takes you up and down along the coast south and west of Otranto, where you'll see the easternmost and southernmost point of Puglia - a spectacular sight! You can also visit the Castel di Salve winery on your way to Santa Maria di Leuca, which is known as De Finibus Terrae, 'the end of the earth', before taking a shuttle back to the hotel.
You stay at the Hotel San Giuseppe (breakfast included)

Day 10: Otranto to Lecce (37km/23.0mi)

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

Day 11: Leave Lecce

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.

To find out more call our sales team on 0044 1606 720199, use our live webchat or email sales@headwater.com


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Relais Corte Altavilla, Conversano

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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.

Local tourist tax not included (pay hotel locally)


Room upgrades: Junior Suite .
The Junior Suite has charming furniture with a living room and panoramic view.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Trullidea, Alberobello

A unique and authentic experience staying in a trulli, a traditional 15th century Apulian stone building with conical roof.

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

The trullis are located in the centre of historic Alberobello, a UNESCO world heritage site, within walking distance of cafes, restaurants and shops.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Masseria San Martino, Pezze di Greco

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


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Albergo Diffuso Monopoli, Monopoli

Hair dryer icon NEARBY: Swimming Pool Icon

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 the hotel's central cafe and dinner will be in a good local restaurant.

Local tourist tax not included (pay hotel locally)


Room upgrades and extra nights: Contact us for details.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel San Giuseppe, Otranto

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Hotel San Giuseppe is set in a 16th-century farmhouse typical of the Puglia region, only 350 yards from the sea in Otranto's historic centre. It offers air-conditioned rooms and which have been restored in a modern style that preserves the flavour of the old farm.They feature high ceilings and tiled floors, and are equipped with a minibar and satellite TV featuring free Sky channels including sports, cinema and entertainment.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Resort Hotel Risorgimento, Lecce

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Featuring a roof-top restaurant with panoramic views, the Risorgimento Resort is located in Lecce's Baroque historic centre. It offers free WiFi throughout, large modern rooms, and a relaxing spa.

Rooms are air conditioned and come with a minibar and satellite TV. Each has a marble bathroom with bathrobes and slippers. The attentive staff provide a continental buffet breakfast. The 3 restaurants offer both Salento flavours and classic Italian cooking. Alternatively there are plenty of good restaurants nearby. Drinks and snacks are available all day at the Janet Ross Bar.

The health club offers a Turkish bath and multisensory shower. Massage and beauty treatments are also available.The hotel doesn't have a pool but there's everything else! Its even got it's own golf course (3km away)!

Piazza Sant'Oronzo is just 100 yards from Risorgimento Resort . The Cathedral is a 5-minute walk away.


Room upgrades: Deluxe Double, Executive, Junior Suite or Garden Suite.

Travel

Call now to speak to our specialist team at 0044 1606 720199 or email us at sales@headwater.com for enquiries or to book your trip.

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 an overall rating and comments about their holiday.

Any feedback collected is posted to our website, so that people can make an informed decision based on past experiences before heading off on holiday. We don’t edit the reviews, the only thing we do is proofread them and alter any typos, where necessary, to ensure they are easy to read for everyone. All reviews will be published (except in certain extreme circumstances), and a member of the Headwater team will respond to any constructive criticisms/comments under the reviews, at their discretion. So, for the real tales, twists and turns of our holidays, look no further than the reviews from our previous travellers.


Michael John Wilson-maccormack, 23/10/2023

Such a great way to experience a destination. The routes allow you to soak up the landscape and the culture at a leisurely pace. It actually covering significant areas over the course of the holiday. The optional routes make for a great opportunity to delve deeper and widen your experience.

Hotels are well selected and in great locations to allow you dip in to the local food scene - always well deserved at the end of days cycling. We always feel recharged at the end of holiday with a stack full of great memories


HELPS, 20/05/2023

This cycling trip in Puglia was wonderful. All accommodations and locations were excellent. This area of Italy was new to us and it didn’t disappoint. The range of areas and experiences was excellent from staying in Trulli to Masserias and quirky auberges. The support of the local agent was excellent and they were so supportive when one of our party had an injury. There was probably more road cycling than compared with other cycling trips we have done but mostly they were quiet. We would definitely recommend this as a trip and hope to visit other parts of Puglia.


Mrs Hope, 24/09/2022

The trip went like clockwork.Headwater delivered the entire y like clockwork .


Mrs Mccartney, 22/08/2022

This was an amazing holiday. From the time of booking to the completion of the tour all ran smoothly. The app for navigation was brilliant - would only go on trips like this in future if this app was used. Puglia Cycling who did our transfers were always on time and very pleasant. Luggage was delivered by 4 pm each day, often earlier and usually waiting in room for us.

The weather was hot but a breeze kept it comfortable. Plenty of water is essential. It is worth noting that in some towns the public toilets are locked during siesta time but restaurants/bars were still open. There are many beaches and swimming holes along the way to stop and have a dip.

Unforgettable. Thank you to Headwater and Puglia Cycling.


Mrs Blease, 30/05/2022

This seemed much harder than the other 1+ Dolomites to Lake Garda cycling holiday we have done despite our fitness being better. However this was probably largely due to an Italian heatwave in late May/early June when we travelled with the thermometer at 30C in the shade each day by 9am. Thoroughly enjoyed it though and were very glad we chose the 10 rather than 7 night option. The extra nights further south contrasted well and it was good to cycle by the sea. Hotels all of good quality and each had its own special qualities. Not being tecchies and with basic phone contracts had some concerns re the GPS app pre travel but after a few minutes on the first morning we coped fine with it. Much easier than the old paper instructions. Had taken a battery charger pack but never used more than half a phones battery whilst out. Amazed how cheap prices were when stopping for drinks in small rural villages eg 1 euro for usual menu of coffees


Dr Taylor, 05/09/2020

excellent itinerary with lots of variety .

excellent local support when we needed it


Mrs Rodely, 01/06/2019

Puglia is a super place to visit, the scenery is stunning, the towns so beautiful and interesting, the routes well planned and the assistance wonderful.



Dates and prices

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.

This 10 night self-guided cycling holiday includes:

Hotel-to-hotel accommodation in a mix of , , and hotels

All continental breakfasts and 2 evening meals included

Bike fitting and briefing at the start of your holiday

Headwater navigation app for your smartphone

Bike hire

Standard transfers at the start/end of the trip (if booking inclusive flights)

Luggage transfers between hotels


How to book:

To book this holidays speak to our sales team on 0044 1606 720199 or click on the appropriate 'book now' or 'check availability' button below.

To book this holiday call our sales team on 0044 1606 720199 or click on the appropriate 'Book now' or 'check availability' button below.

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27th Aug 2025 US$4400 US$609 Tour only: US$4400
Single supp: US$609
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Check availability
30th Aug 2025 US$4400 US$609 Tour only: US$4400
Single supp: US$609
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Check availability
DepartingTour only Prices   Single supplement
1st Sep 2025 US$4400 US$609 Tour only: US$4400
Single supp: US$609
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Check availability
3rd Sep 2025 US$4400 US$609 Tour only: US$4400
Single supp: US$609
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Check availability
6th Sep 2025 US$4400 US$609 Tour only: US$4400
Single supp: US$609
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Check availability
8th Sep 2025 US$4400 US$609 Tour only: US$4400
Single supp: US$609
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Check availability
10th Sep 2025 US$4400 US$609 Tour only: US$4400
Single supp: US$609
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Check availability
13th Sep 2025 US$4400 US$609 Tour only: US$4400
Single supp: US$609
Check availability
Check availability
15th Sep 2025 US$4400 US$609 Tour only: US$4400
Single supp: US$609
Check availability
Check availability
17th Sep 2025 US$4400 US$609 Tour only: US$4400
Single supp: US$609
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Check availability
20th Sep 2025 US$4400 US$609 Tour only: US$4400
Single supp: US$609
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Check availability
22nd Sep 2025 US$4400 US$609 Tour only: US$4400
Single supp: US$609
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Check availability
24th Sep 2025 US$4400 US$609 Tour only: US$4400
Single supp: US$609
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Check availability
27th Sep 2025 US$4400 US$609 Tour only: US$4400
Single supp: US$609
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Check availability
29th Sep 2025 US$4400 US$609 Tour only: US$4400
Single supp: US$609
Check availability
Check availability
DepartingTour only Prices   Single supplement
1st Oct 2025 US$4175 US$609 Tour only: US$4175
Single supp: US$609
Check availability
Check availability
4th Oct 2025 US$4175 US$609 Tour only: US$4175
Single supp: US$609
Check availability
Check availability
6th Oct 2025 US$4175 US$609 Tour only: US$4175
Single supp: US$609
Check availability
Check availability
8th Oct 2025 US$4175 US$609 Tour only: US$4175
Single supp: US$609
Check availability
Check availability
11th Oct 2025 US$4175 US$609 Tour only: US$4175
Single supp: US$609
Check availability
Check availability
13th Oct 2025 US$4175 US$609 Tour only: US$4175
Single supp: US$609
Check availability
Check availability
15th Oct 2025 US$4175 US$609 Tour only: US$4175
Single supp: US$609
Check availability
Check availability
18th Oct 2025 US$4175 US$609 Tour only: US$4175
Single supp: US$609
Check availability
Check availability
20th Oct 2025 US$4175 US$609 Tour only: US$4175
Single supp: US$609
Check availability
Check availability
22nd Oct 2025 US$4175 US$609 Tour only: US$4175
Single supp: US$609
Check availability
Check availability
25th Oct 2025 US$4175 US$609 Tour only: US$4175
Single supp: US$609
Check availability
Check availability
27th Oct 2025 US$4175 US$609 Tour only: US$4175
Single supp: US$609
Check availability
Check availability
29th Oct 2025 US$4175 US$609 Tour only: US$4175
Single supp: US$609
Check availability
Check availability

The prices quoted for each individual departure supercede those published in our current brochures. Air prices are subject to change and we advise early booking to obtain the best prices. Please see our Planning your holiday and What's included in the price? pages for additional information.

Holiday details

Solo travellers
Please call for details and prices

Children
This holiday is unsuitable for children.

Holiday type
Self-guided cycling Managed by Headwater rep.

Departures
selected Mons, Weds & Sats from 24th Apr 2024 to 29th Oct 2025, for 10 nights. All dates are subject to availability, please contact us to check.

Meals
All continental breakfasts and 2 evening meals included

Electric bikes
It is possible to hire electric bikes for this holiday at a supplement of £364 per person. As these are available on a first come first served basis, we recommend early booking to avoid disappointment.

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

Tailor-made travel

Tour only

How to book

To book this holidays speak to our sales team on 0044 1606 720199 or click on the appropriate 'book now' button above.

If you need further information before you book simply complete our Holiday Enquiry Form and a member of our sales team will get back to you.

To book this holiday call our sales team on 0044 1606 720199 or click on the appropriate 'Book now' or 'Check availability' button below.