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Self-Guided Leisure Cycling Holiday




8 days

Prices from

£1,225 P.P.


This holiday is well-suited to both normal bikes and pedal assist e-bikes and you can choose to hire either when you book your holiday with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities.

A self-guided cycling holiday exploring the Apulian region of Italy, dipping into Basilicata to discover Matera. Located in the Southeast, in what is commonly known as the heel of Italy's boot, this lesser-discovered region combines glistening ocean views, authentic Italian towns and lush olive groves, offering a cycling treat!
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 cycle tour will take you into a region of stunning, unspoilt beauty. Starting in Gravina in Puglia, your first ride will take you to Matera. Crowned as the European Capital of Culture in 2019, Matera is famous for its Sassi quarter, now a World Heritage Site.  Riding on through ancient olive groves and narrow country lanes, you'll reach Alberobello, a town made up of Trulli houses where you'll stay for two nights.
After exploring this fascinating Trulli region you'll carry on to Ostuni, known as 'La Citta Bianca', thanks to its pristine, white-washed buildings. Your rest day will offer the opportunity to jump on the train to Lecce, the "Florence of the South", where you'll discover awe-inspiring architecture and vibrant streets filled with wine bars. 
Heading north you'll soon reach the Adriatic coast, enjoying stunning coastal views and exploring the idyllic towns of Monopoli and Polignano a Mare. Your final destination, Polignano a Mare, boasts a charming old town, beautiful beaches and culture to boot, making it the ideal spot to reflect on your week of cycling.

Holiday Highlights

  • Cycling through lush landscapes of ancient olive groves and vineyards
  • Exploring the UNESCO World Heritage town of Alberobello
  • Discovering the traditional Trulli houses of Puglia
  • Relaxing each evening in comfortable hotels in authentic towns and villages
  • Stopping at beautiful, sandy beaches with turquoise seas
  • Tasting delicious local products, like extra virgin olive oil and Primitivo wine

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Day 1
Arrival into Bari Airport - Transfer to Gravina in Puglia

You will be met at the airport and transferred to your accommodation in Gravina in Puglia (transfer approx. 1 hour). A local representative will fit you to your bikes (if renting) and conduct your welcome meeting. It’s a good chance to ask any questions you may have about the week ahead.

If time allows we recommend exploring the historic centre of Gravina in Puglia. Highlights of the city, the birthplace of Pope Benedetto XIII, include the main Basilica, the many rock cut churches, including the sanctuary of Madonna della Stella and the amazing Ponte Aquedotto Bridge spanning the local gorge, and of James Bond fame!

Day 2
Gravina in Puglia to Matera
22 Miles / 36 Kms Approx.
  • Meals: Breakfast
  • Ascent: 400 Metres Approx.

Heading out on your bikes this morning you’ll loop round through Murgia, as you cycle through a picturesque landscape of open fields and countryside.

Your ride today will end with a climb up to the awe-inspiring Matera, perched on a rocky outcrop. Matera, known as the ‘City of Caves’ is a wonderful place to explore. Take a look at the city agenda for events: the town was the European Capital of Culture in 2019 so lots of things to watch out for!

As the distance today is a little shorter than other days, you should have some extra time for exploring. You could either set off a bit later, and explore Gravina a bit more in the morning, or head straight for Matera and spend some more time there.

Day 3
Matera to Alberobello
43 Miles / 70 Kms Approx.
  • Meals: Breakfast
  • Ascent: 550 Metres Approx.

Today you’ll leave Matera following quiet, country roads through glorious Apulian countryside. You’ll follow a rollercoaster route, surrounded by olive trees, as you reach the famous area of the Trulli houses. Look out for authentic houses scattered along the route, as you make your way towards Alberobello: the Trulli capital of the world. The town is today a UNESCO World Heritage Site and one of the best preserved of its type in Europe. The 1,000 Trulli houses, many of which are still lived in, will transport you to an entirely different world. This evening you can wander around Alberobello and enjoy a meal in one of the many restaurants.

Day 4
Alberobello Loop
29 Miles / 50 Kms Approx.
  • Meals: Breakfast
  • Ascent: 550 Metres Approx.

Today you’ll follow a circular route, leading you through more distinctive Apulian landscape. The Valle d‘Itria, boasts quiet, country roads and cycle paths, that offer relaxed and varied cycling. Your route will lead you through Putignano and Castellana, where you’ll have the option to visit an impressive underground cave system (payable locally). You’ll once again be spending the night in Alberobello, where you can indulge in some delicious local cuisine, as well as visit the impressive basilica.

Day 5
Alberobello to Ostuni
28 Miles / 45 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 destination for today is Ostuni, where you’ll spend the evening. Known as ‘La Citta Bianca‘, or the White City, Ostuni sits majestically on a hill, offering spectacular views out to the Adriatic. Spend the evening exploring Ostuni’s narrow streets within its protective walls, stopping to admire the Gothic, 15th-century cathedral.

Day 6
Rest Day
Non-Cycling Day
  • Meals: Breakfast

Today is a day off the bikes, and we’d recommend visiting Lecce! A short ride will take you to Ostuni train station where you can leave your bikes and board the train (tickets not included). Upon arrival into Lecce, you’ll discover a brilliant city full of wonderful palaces and treasures, that will leave you mesmerised. Lecce is known as the “Florence of the South” with magnificent Baroque churches and squares to be discovered. It also offers a range of wine bars and restaurants, serving up fresh, local produce.

Jumping on the train back to Ostuni, you should have plenty of time to spend another relaxing evening in this beautiful city.

Day 7
Ostuni to Polignano a Mare
32 Miles / 52 Kms Approx.
  • Meals: Breakfast
  • Ascent: 200 Metres Approx.

Today you’ll make your way to the coast! Leaving Ostuni behind, you’ll head for the Adriatic enjoying a mix of countryside and coastal riding. En route you’ll have the opportunity to visit the ancient town of Egnazia the best Roman ruins in the region.

Following the coastline, you’ll arrive in Monopoli, with its charming mix of Norman, Venetian-Byzantine and Arabic architecture. Monopoli is a great place to stop for a spot of lunch, and perhaps take a dip in the crystal-clear Adriatic. From Monopoli it’s about 6 miles/10 kms to your destination, as you ride north-west, until you reach Polignano a Mare. Polignano is a vibrant fishing village perched on cliffs and surrounded by clear blue waters. Visit the statue of Domenico Modugno, enjoy a spritz in the historic town centre, or take one last dip in the warm waters! This is the ideal location to enjoy your last evening in Puglia.

Day 8
Departure from Polignano - Transfer to Bari Airport
  • Meals: Breakfast

Arrivederci Puglia! Time to head to the airport for flights home. (Transfer approx. 40 minutes.)

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The Cycling


You’ll ride on a mixture of flat and rolling countryside, mainly on quiet country roads. Some roads will have local traffic especially leading into the towns, but generally the roads in Puglia are quiet. Please be aware that some roads in this area are not in a great condition.

Day 2 sees some short, steep climbs and Day 3 will be the toughest, with the longest distance and some cheeky climbs. Although this may be a challenge for a grade 2 rider, the majority of the route is gentle, hence the overall grade 2 rating.

We recommend a hybrid bike for this tour, due to some short sections over gravel / dirt roads, however a road or gravel bike would suffice (with some minor diversions).

If you’re wanting to spend more time exploring the towns and villages along the way, then an e-bike is a great idea to cover the miles a little quicker. An e-bike would also help those in need of a little boost (particularly if riding in September when it can get quite hot) to cover some of the longer distances, and cheeky climbs early in the week.

For more information about riding an electric bike on our holidays please click here


Leisure Cycling Grade

Grade 2: Gentle

Distances generally between 15-30 miles / 24-48 kms per day

For those looking for an easy-going route

Mainly on the flat

Some undulations and the odd cheeky challenge

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 have recently got into cycling and would like to do more over consecutive days, or maybe you‘re looking for a more energetic alternative to your usual holiday? If you‘re looking for an opportunity to try some quiet roads, cycle paths or some accessible, cycle friendly routes these holidays might be for you. You’ll come across some gently undulating terrain and the odd cheeky challenge, so we’d generally expect those on a Grade 2 holiday to ride their bikes relatively frequently at home, perhaps commuting to work or heading out for some leisurely rides at the weekend.

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 departures from 09 Jun to 31 Aug)

Season 1 – £1425 03 Apr – 08 Jun / 10 Sep – 30 Oct

Season 2 – £1595 25 Mar – 02 Apr / 01 Sept – 09 Sept

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

Season 1 – £1495 24 Mar – 08 Jun / 09 Sep – 29 Oct

Season 2 – £1675 25 Mar – 01 Sept – 08 Sept

Alternatively for a great value holiday choose one of our scheduled departures below.

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.

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8 days
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Whats Included Tick

A) Accommodation (shared twin / double rooms) in good quality 3* hotels, B&Bs and guesthouses

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 an 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) Single room (available if required)

D) Travel insurance

E) Meals not stated in the itinerary

F) Personal clothing and equipment

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

H) Entrance fees to museums and other attractions

I) Train tickets from Ostuni to Lecce (Day 6) payable locally (€10 approx.)

J) Possible city tax to be paid locally in cash (approx €15)

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

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The Essentials

Travel Options

Your tour starts in Gravina in Puglia and finishes in Polignano a Mare.

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.

If you are joining one of our scheduled departures we will provide arrival and departure times, along with suitable flight options, as and when more flight schedules are released.

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 and 4* hotels, B&Bs and guesthouses all with en suite facilities, which have been carefully selected for their location, cuisine and service.

We also have an upgrade option available, which will see you staying in 4* hotels that are often located in the historic centre of town. This option will still include at least one stay in a high-quality guesthouse. Please select this option at the time of booking.

Bike Hire

If you don’t own a suitable bike or would prefer to avoid bringing your own we have bikes available to rent. These bikes are typically Specialized Crosstrail Sport hybrid bikes (or equivalent).

We also have electric bikes available to rent on request. These bikes are typically Atala B Tour E-Bikes (or equivalent). It may take us a day or so to confirm availability so please let us know as soon as possible if you’d like to take this option

Rental bikes will be provided with a pannier rack and 1 bag, a tool kit, a spare inner tube, a bike lock, a bike pump and a phone mount.

We can provide a helmet locally on request, please let us know if you’d like to rent one when you make your booking.

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