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Puglia - The Beautiful South

Self-Guided Road Bike Tour




8 days

Prices from

$1,945 P.P.
A self-guided cycling holiday exploring the Apulian 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 cuisine to unique architecture.
Your route starts in the very southern tip of Puglia, at Santa Maria di Leuca. From here you will 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 you will transfer by train to the 'White Town' of Ostuni from where you cycle through ancient olive groves to Cisternino, reaching Alberobello in the evening, a town made famous by its ‘Trulli’ houses.
From Alberobello you explore the local countryside passing by Putignano and Monopoli.
Your final destination for this week is Matera, just over the border into Basilicata, famous for the '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 churches of Lecce
  • Exploring the gnarled olive groves in the countryside of Alberobello
  • Enjoying the sights of 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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We enjoyed most of the cycling but we really enjoyed cycling near the coast where the views were stunning.

June, UK


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

After arrival at Bari airport (BRI), we take you on the 3 hour transfer to Santa Maria di Leuca where there will be time to assemble your 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 waters, where the Adriatic and the Ionian seas divide. A difficult view to leave behind but there are plenty of beautiful views ahead of us!

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

Today the journey by bike begins. From Santa Maria you head north along the high coastal road and wind your way along the cliff tops with magnificent views along the way. You’ll be riding past rocky coves, heading ever further away from the furthest tip of the heel of Italy. On your way you 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 you arrive at Otranto, a Greco-Roman port frequented by merchants and thrill seekers. As you enter the old town, you will notice the wall surrounding the Hapsburger Castle.

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

Setting off on your bikes this morning you head inland through the countryside of the Salento, where you’ll find traces of former Greek colonies still present in the dialect, cuisine and architecture.

Weaving your way through cultivated fields you reach the little hamlet of Acaya dominated by its enormous castle. We recommend a coffee break here before you then head further north into the gnarled olive groves and take the road leading into 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.

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

After breakfast you have more time to explore Lecce, taking in its marvellous churches and palaces before transferring by train to the white town of Ostuni with its narrow streets within its protective walls and the Gothic 15th century cathedral.

From Ostuni you 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. You’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 itself 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. You’ll be spending the night in Alberobello where you can indulge in some delicious local cuisine.

Day 5
Alberobello Loop Ride
37 Miles / 60 Kms Approx.
  • Meals: Breakfast
  • Ascent: 750 Metres Approx.

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

On reaching the coast you 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 you then loop back through the country side to Alberobello where you 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
  • Ascent: 550 Metres Approx.

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

Leaving Alberobello your route today takes you through the distinctive Apulian landscape. Heading inland, you ride cross country past cultivated fields and make your 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
  • Ascent: 1000 Metres Approx.

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

This ride will take you 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 aperitivo and a last delicious meal.

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

Arrivederci Puglia! Time to head to the airport for your flight home. (Transfer time 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. Some of the countryside roads have some potholes where surface conditions have deteriorated.


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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Dates & Prices

Daily departures available. The season prices below are per person and are applicable for all start dates between and inclusive of the stated dates.

2023 25 Mar – 30 Oct (excluding dates from 18 Jun – 26 Aug)

Season 1 – $1945 25 Mar – 05 Apr, 15 Apr – 17 Jun and 10 Sep – 30 Oct

Season 2 – $2155 06 Apr – 14 Apr and 27 Aug – 09 Sep

2024 25 Mar – 30 Oct (excluding dates from 09 Jun – 31 Aug)

Season 1 – $2075 03 Apr – 08 Jun – 10 Sep – 30 Oct

Season 2 – $2305 25 Mar – 02 Apr – 01 Sept – 09 Sept

Choose your date
Start Date
End Date
Price p.p.
Start Date
Return Date
8 days

Whats Included Tick

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

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

C) Local representative (with welcome meeting)

D) Access to the Skedaddle App for holiday information and navigation

E) Luggage transfers

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

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

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 tickets from Ostuni to Lecce (Day 4) payable locally (€10 approx.)

J) Local tourist tax, approx 2 euros per day, normally paid on check-out

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

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The Essentials

Travel Options

This tour starts in Santa Maria di Leuca and finishes in Matera.

Airport transfers are included in the cost of your holiday. We ask that you fly into and back from Bari airport (BRI). Please aim to arrive between 09:00 and 16:00 and depart between 11:00 and 19:00.

Please check with Skedaddle before making any travel arrangements.

Please note If you make travel arrangements that fall outside of the above time windows there may be an additional charge for your transfers.


You’ll be staying in centrally located, comfortable 3 star hotels all with en-suite facilities, which have been carefully selected for their location, local cuisine and service.

If you would like us to check out accommodation upgrade options for you, please contact us for further details.

Bike Hire

Rental bikes are typically Specialized Allez road bikes. They are great bikes with good quality components and generally come equipped with at least one bottle cage, a saddle bag, a phone mount 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. You are welcome to bring your own saddle if you wish to.

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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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