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Puglia - The Beautiful South

Self-Guided Road Cycling Holiday




8 days

Prices from

£1,575 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 at the town made famous by its 'Trulli' Houses: Alberobello. From here you will head south along the Adriatic Coast to the 'White Town' of Ostuni 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 then cycle to Gallipoli, a town steeped in history and ancient charm.
From Gallipoli, you'll explore the local countryside travelling to the southern tip of Puglia at St Maria di Leuca and onwards to Otranto which boasts an enchanting blend of historic charm, turquoise Adriatic waters, and the mesmerizing mosaic floor of its medieval cathedral.
You will then traverse once again to your final destination for this week, Lecce, to soak in more of the captivating Baroque architecture the town has to offer.
If you would like to extend your stay and visit Matera, we can arrange an extension at the start of the trip with an extra day’s riding, please chat to our team.

Holiday Highlights

  • Savouring the deep red wine of the Salento region and the crisp whites of Locorotondo
  • Enjoying the sights of Alberobello, famous for the ‘trulli’
  • Exploring the gnarled olive groves in the countryside of Alberobello
  • Visiting 2 UNESCO heritage sites; Lecce and Alberobello
  • Admiring the Baroque churches of Lecce
  • Enjoying the panoramic coastal road between Santa Maria di Leuca and Otranto

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We enjoyed most of the cycling but we really enjoyed cycling near the coast where the views were stunning.

June, Angus


Day 1
Arrival: Bari / Alberobello
Non Riding Day

After arrival at Bari airport (BRI), we take you on the approx. 1 hour transfer to Alberobello where there will be time to assemble your bikes before dinner.

Alberobello, a UNESCO World Heritage Site, is an enchanting town with iconic ‘trulli’ houses, narrow streets, and the unique Trullo Sovrano museum. The picturesque Rione Monti and the charming Trullo Church of Sant‘Antonio are must-sees!

Day 2
Alberobello Loop Ride
37 Miles / 60 Kms Approx.
  • Meals: Breakfast
  • Ascent: 750 Metres Approx.

Your first ride out today will be 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 3
Alberobello to Ostuni (Train to Lecce)
25 Miles / 40 Kms Approx.
  • Meals: Breakfast
  • Ascent: 400 Metres Approx.

Today you’ll be riding through the historically-rich “Murgia degli Trulli” area along quiet roads surrounded by olive groves, vineyards and traditional masserie (typical farm houses of Puglia). You’ll pass through the medieval towns of Cisternino and Locorotondo, both of which are worth jumping off your bikes to explore their centres. Cisternino has a spectacular viewpoint, from where you can see the lush Valle d‘Itria.

Your arrive at Ostuni which sits majestically on a hill, offering spectacular views out to the Adriatic: From Ostuni you will catch the train to Lecce, but you have time to explore ‘La Citta Bianca‘, or the White City as it is known. Your destination after the train ride is 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
Lecce to Gallipoli
29 Miles / 50 Kms Approx.
  • Meals: Breakfast
  • Ascent: 250 Metres Approx.

Gallipoli is our destination for the evening, and is known as the “Ionian Pearl”. Throughout history, Gallipoli has been an important fishing and trading port. First, the route takes you from Lecce across countryside and olive groves towards the west coast where you drop down to the sea by the whitewashed town of Santa Catalina and can enjoy the last 10 miles of coastal riding before reaching Gallipoli.

The rest of the day is yours to spend as you please. You may want to visit one of the ancient underground olive-mills still preserved and open to the public, or take a stroll near the harbour. Or you could meander through the narrow alleys and explore the many little churches, or perhaps just relax in one of the town squares, before taking in the breathtaking sunset from the historic town.

Day 5
Gallipoli to St Maria di Leuca
33 Miles / 55 Kms Approx.
  • Meals: Breakfast
  • Ascent: 180 Metres Approx.

Today you’ll ride following the Ionian sea heading towards the heel of Italy where the Ionian and Adriatic sea meet, riding past long sandy beaches and little coves. You’ll notice some beautiful beaches, dotted with beach clubs that fill up during the summer months such as Maldive del Salento. Arriving in Santa Maria di Leuca, a small village with colourful “mansions” and a beautiful lighthouse, there will be time to dip into the crystal clear sea where the Adriatic and the Ionaian seas divide.

Day 6
St Maria di Leuca to Otranto
35 Miles / 55 Kms Approx.
  • Meals: Breakfast
  • Ascent: 650 Metres Approx.

From Santa Maria you’ll 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 7
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. Lecce is renowned for its ornate Baroque buildings, ancient Roman ruins, and a lively atmosphere, making it a popular destination for art, history, and architecture enthusiasts.

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

Arrivederci Puglia! Time to head to the airport for your flight home. (Transfer time approx. 2 hours).

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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 60 km over mixed terrain with the occasional cheeky climb. Grade 2 could be for you.

For more information about the grading of this holiday in particular, please check out the terrain section which will give you some specifics of what to expect on this tour.

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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.

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

Season 1 – £1575 03 Apr – 08 Jun / 10 Sep – 30 Oct

Season 2 – £1725 25 Mar – 02 Apr / 01 Sept – 09 Sept

2025 24 Mar – 29 Oct (excluding dates from 09 Jun – 31 Aug)

Season 1 – £1655 24 Mar – 08 Jun / 09 Sep – 29 Oct

Season 2 – £1815 01 Sept – 08 Sept

Secure Your Holiday With A Deposit

Book now with a £200 deposit and nothing more to pay until 60 days before departure. Choose a date to start your booking and see all prices, including bike hire and single room supplements.

Select a date to view prices and book
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) English-speaking local representative (with either an in-person or video call welcome meeting)

D) Access to the navigation 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)

H) 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 tickets from Ostuni to Lecce (Day 3) 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 Alberobello and finishes in Lecce.

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

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Meet the guides: Antonio

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Meet the guides: Cristina Navarra

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



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