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Puglia - The Beautiful South

Guided Road Bike Tour




8 days

Prices from

$2,475 P.P.
A guided road cycling holiday exploring the Puglian region of Italy, located in the southeast of what is commonly known as the Heel of Italy’s Boot, and also its best kept secret!
This interesting and eclectic region is steeped in history and has been governed by the Greeks, Romans and Spaniards over the centuries, each leaving their own distinctive mark, from local dialects and flavoursome cuisines to unique architecture. 
Our Puglia cycling route starts in the very southern tip, at Santa Maria di Leuca. From here we head north along the Adriatic coast to Otranto and to Lecce, the 'Florence of the South', located in the heart of the Salento area.
After a visit to the old town of Lecce we transfer by train to the 'White Town' of Ostuni from where we cycle through ancient olive groves to Cisternino, reaching Alberobello in the evening, a town made famous by its ‘trulli’ houses. From Alberobello we explore the local countryside passing by Putignano and Monopoli.
Our final destination for this week is Matera, just over the border into Basilicata, famous for its 'sassi', a whole town's houses carved out of the soft rock where people have lived for over 9,000 years! 


  • Enjoying the panoramic coastal road between Santa Maria di Leuca and Otranto
  • Admiring the baroque style churches of Lecce
  • Exploring the gnarled olive groves in the countryside around Alberobello
  • Enjoying the sights at Alberobello famous for the ‘trulli’
  • Visiting 3 UNESCO heritage sites; Lecce, Alberobello and Matera
  • Savouring the deep red wine of the Salento region and the crisp whites of Locorotondo

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I really enjoyed the trip and loved the Trulli and Sassi experience. The guides were all passionate about Puglia, they really gave the trip a local flavour!

Peter, UK


Day 1
Arrival: Bari / Santa Maria di Leuca
Non Riding Day

After arrival in Bari airport (BRI), we take the 3 hour transfer to Santa Maria di Leuca where there is time to assemble the bikes before dinner and to have a wander along the seaside boulevard, taking in the atmosphere of this little seaside town at the very tip of Puglia.

The village is dotted with colourful and alternative ‘mansions‘, and surrounded by crystal clear sea, where the Adriatic and the Ionaian seas divide. A difficult view to leave behind but there are plenty beautiful views ahead of us!

Day 2
Santa Maria di Leuca to Otranto
34 Miles / 55 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 650 Metres approx.

From Santa Maria we head north along the high coastal road and wind our way along the cliff tops with magnificent views along the way. We’ll be riding past rocky coves, heading ever further away from the furthest tip of the heel of Italy.

On our way we will pass the well-known Grotta Zinzulusa and the village of Santa Ceserea Terme, known for its thermal baths. At the end of the day we arrive at Otranto, a Greco-Roman port frequented by merchants and thrill-seekers. As we enter the old town, we will notice the remarkable wall surrounding the Hapsburger Castle.

Day 3
Otranto to Lecce
37 Miles / 60 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 250 Metres Approx.

Setting off on our bikes this morning we head inland through the countryside of the Salento, where we’ll find traces of former Greek colonies still present in the dialect, cuisine and architecture. Weaving our way through cultivated fields we reach the little hamlet of Acaya, dominated by its enormous castle.

After a coffee break we then head further north into the gnarled olive groves near Lecce. Here we may stay in a wonderful family-run accommodation located in a masseria about 15km outside the town, or alternatively in a comfy hotel in the lively town of Lecce itself.

Day 4
Visit Lecce - Ride Ostuni to Alberobello
25 Miles / 40 Kms Approx.
  • Meals: Breakfast
  • Ascent: 600 Metres Approx.

This morning we will have time to visit the old town of Lecce, a brilliant city of wonderful palaces and treasures which will leave you mesmerised! Known as the ‘Florence of the South‘, Lecce’s Baroque architecture is some of the finest of Italy. We make time for a visit of the town taking in its marvelous churches and palaces.

With your own time to wander the streets, your lunch choices today are your own, before we transfer together by train to the white town of Ostuni with its narrow streets within its protective walls and the Gothic 15th century cathedral. From Ostuni we then head north again, cycling through the historically rich Valle d‘Itria, weaving amongst olive groves, vineyards, traditional masserie farm houses (typical farm houses of Puglia) and trulli. We’ll pass through the medieval towns of Locorotondo, famous for its white wine, and on to Alberobello, passing the famous fairy-tale ‘trulli’ houses that awarded Alberobello its title as a UNESCO World Heritage site. The 1,000 trulli houses, many of which are still lived in, will transport us to an entirely different world. We’ll be spending the night in Alberobello where we can indulge in some delicious local cuisine.

Day 5
Alberobello Loop Ride
40 Miles / 65 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 750 Metres Approx.

On our second day in Alberobello we will go out for a loop ride through the countryside between Alberobello and the Adriatic coast. Leaving Alberobello in the morning our route today takes us through the distinctive Puglian landscape, via Putignano and Castellana where we have the option to visit an impressive underground cave system (payable locally).

On reaching the coast we arrive in the town of Monopoli, with its charming mix of Norman, Venetian-Byzantine and Arabic architecture. The old town is a perfect spot for a coffee break. From Monopoli we then loop back through the countryside to Alberobello where we will arrive with plenty of time to spare to further explore this most charming of towns.

Day 6
Alberobello to Matera
46 Miles / 75 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 550 Metres Approx.

Our destination for today is Matera, yet another UNESCO World Heritage site.

Leaving Alberobello our route today takes us through the distinctive Puglian landscape. Heading inland, we ride cross country past cultivated fields and make our way to Matera. Famous for its historical centre, the inhabitants of this region carved dwellings directly into the ravines made of tuff (tufa in italian), a light coloured soft stone. These dwellings are called ‘sassi’ and are a UNESCO World Heritage Site. These houses are still lived in and are unique in the world.

Day 7
Matera Loop Ride
56 Miles / 90 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 1000 Metres Approx.

On the last riding day of the week and you have the choice to chill out in the amazing town of Matera, and visit some of its wonderful monuments, or join a loop ride taking us from Matera further into the wild and hilly Basilicata region, before looping back towards Matera.

This ride will take us on a panoramic route over the Murgia Plateau, passing by the medieval towns of Gravina in Puglia, dominated by its deep narrow gorge, and Altamura famous for its cathedral, and its bread! After returning to Matera you will have the time to pack up your bikes and freshen up before hitting the town for aperitif and a last delicious meal.

Day 8
Departure: Matera / Bari
Non Riding Day
  • Meals: Breakfast

Arrivederci Puglia!

Time to head back to Bari airport for flights home and we leave the hotel early to get you to the airport in time for your flights home.

Transfer time to the airport – approx. 75 minutes).

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The Cycling


Your tour will take you through a mixture of flat and rolling countryside, mainly on quiet country and coastal roads with great views. The section along the coast is more of a rollercoaster and there are busier sections when entering and leaving Lecce.


Road Cycling Grade

Grade 2 : Gentle

40-50 miles / 60-80 kms per day

On undulating or rolling terrain, occasional moderate / challenging climbs

No high altitude ascents & the odd short steep climbs

For semi-regular riders / relative novices wishing to gain experience & fitness

Our grading guidelines have been carefully created based on our many years of cycling experience, as well as customer feedback from our trips. Of course, if you're still struggling to figure out where you fit on the scale, do feel free to give us a quick call and we'll be more than happy to help!

For more information about our grading system click here.

Is this suitable for you?

Maybe you’re quite new to road biking, you might not have your own road bike but if not, you’re definitely thinking seriously about getting one. You’ve probably ridden a road bike a few times and you’re keen to gain more experience. You’re up for the occasional challenge but big mountains are probably not your thing. You’re happy to spend a few hours on the bike and do so occasionally and casually on the odd weekend. You might see cycling more as a means of transport than a leisure activity and you’re interested in a holiday where there’s at least as much emphasis on sightseeing and relaxing as there is on the riding. A typical day might see you covering up to 40 miles over mixed terrain with the occasional cheeky climb. Grade 2 could be for you.

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We just want to say how much we enjoyed our trip to Puglia cycling, it was everything we had hoped for and more.

Elaine and Phil, UK

Dates & Prices

Secure Your Holiday With A Deposit

Book your trip with a deposit of $250 per person until 60 days before departure.

Choose your dates to start the booking
Start Date
End Date
Price p.p.
Start Date
* 14/10/2023
Return Date
8 days

Late Availability

We want you to know which tours are coming up soon, so you don’t miss out! If a trip has this symbol beside it, it means you don’t have long to snap up your place.

Whats Included Tick

A) Accommodation (shared twin / double en-suite rooms)

B) Meals as per the itinerary (B=Breakfast, L=Lunch, D=Dinner)

C) Full tour service, including Skedaddle guides

D) Unless stated, at least one leader qualified in First Aid

E) Support vehicle and luggage transfers

F) Airport transfer on scheduled arrival day from Bari airport (BRI)

G) Airport transfer on scheduled departure day to Bari airport (BRI)

G) Financial Protection through ABTOT

What's not Included Cross

A) Bike rental (available if required)

B) Flights and charges for travelling with your bike (if applicable)

C) Meals not stated in the itinerary

D) Single room (available if required)

E) Travel insurance

F) Personal clothing and equipment

G) Personal expenditure (souvenirs, bar bills, hotel facilities etc)

H) Entrance fees to museums and other attractions en-route

I) Train ticket from Lecce to Ostuni on day 4 (approx 10 euros)

J) Airport transfers on days other than the scheduled arrival / departure days

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Private Departures

Private Departures

Are you keen to only travel with your family or friends? Struggling to find the right date? Well, we can organise a private departure for this tour and tailor aspects to suit your group's specific needs. Contact our friendly team and we'll help you turn your dream into reality.

The Essentials

Travel Options

Your tour starts in Santa Maria di Leuca and finishes in Matera. Group airport transfers are included in the cost of your holiday.

To join the airport transfer on arrival you’ll need to arrive into Bari Airport (BRI) before 12.30 for a 13.00 transfer.

At the end of the tour, we will transfer the group to Bari Airport with an estimated arrival time of 11.00 – please consider this when booking your return travel and allow enough time to check in for your chosen flight.

Most flights from the US will involve overnight travel, multiple travel days and there may not be direct options to/from Bari. Please chat to our team to discuss suitable options.

Please check with us before making any travel arrangements to ensure we have reached the minimum number required to guarantee your holiday and to make sure your arrangements fit with our scheduled transfers.

Please note: If you make travel arrangements that fall outside of the scheduled transfer windows, there may be an additional charge for individual transfers.


The majority of our accommodation (shared twin or double rooms) will usually be en-suite in 3* hotels or guesthouses.

Bike Hire

If you have opted to rent, your bike will typically be a Giant Defy or Contend with Giant/Liv Avails (alu frames) for those preferring a women’s specific frame. They are great bikes with good quality components, mechanical disc brakes and generally come equipped with at least one bottle cage, a saddle bag and a small pump.

We can also include a helmet which should be requested at time of booking.

Please note that your bike will come with flat pedals as standard, so please do bring your own if you use clip-in pedals.

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News, Reviews & Stories

Meet the guides: Antonio

Catch him in the heel of the boot enjoying the alluring shores of the Adriatic Sea...

Meet the guides: Cristina Navarra

Meet our amazing Italian guide who calls the heel of the Italian boot her home...

Matera City Guide

Discover 2019 European Capital of Culture, enchanting Matera!




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