Headwater - Highlights of Puglia Self-Guided Cycling

11 days
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Self-Guided Holidays
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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 begins in the picturesque coastal town of Monopoli, from where you follow the coast north, passing white sandy beaches and secluded coves with wonderful opportunities for seafood lunches along the way. Head inland and 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'.


  • 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

Key information

  • 10 nights hotel-to-hotel accommodation
  • 9 days cycling (including 3 optional rides)
  • Management by your local Headwater-appointed agent
  • GPS route directions and maps
  • RideWithGPS navigation app
  • High quality bikes
  • Luggage transfers between hotels
  • Countries visited: Italy

What's included

  • All accommodation
  • All continental breakfasts and 3 evening meals
  • Management by your local Headwater-appointed agent
  • GPS route directions and maps
  • RideWithGPS navigation app
  • High quality bikes
  • Luggage transfers between hotels

What's not included

  • Travel insurance
  • Single accommodation - (compulsory)
  • Visas or vaccinations
  • Arrival & departure transfers
Call for general departures:
020 8772 3936
Call for tailormade trips:
020 8772 3874
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.

9 (3 optional rides)

Days of Cycling

The cycle routes mainly follow tarmac country roads.

Day by day breakdown
Day 234.0km/21.5miles
Day 339.0km/24.5miles
Day 445.0km/28.5miles
Day 549.0km/30.5miles
Day 648.0km/30.0miles
Day 737.0km/23.5miles
Day 842.0km/26.5miles
Day 955.0km/34.5miles
Day 1037.0km/23.5miles

Responsible Travel

At Exodus we believe in the power of Responsible Travel.

Every time we travel, we are part of a global movement that creates jobs, builds more sustainable societies, encourages cultural understanding and safeguards common natural and cultural heritage. To learn more about what Responsible Travel means to Exodus click here


  • Day 1

    Arrive at Monopoli

    Arrive at your hotel for a welcome briefing. There's time to discover the historic town of Monopoli before dinner. (Staying at Albergo Diffuso, evening meal at a local restaurant)

    Meals included: Dinner
  • Day 2

    Monopoli to Conversano

    A charming route takes you along the stunning coastline from Monopoli before heading inland to Conversano. En route take time to visit the small, but vibrant fishing village of Polignano a Mare, idyllically perched on the side of the rocky limestone cliffs. Continue through the quaint, picturesque village of San Vito, with its multi-coloured boats moored up in the tiny port, before finishing your journey in the sleepy, beautiful little town of Conversano. (Staying at Relais Corte Atavilla)

    Meals included: Breakfast
  • Day 3

    Conversano to Alberobello

    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. (Staying at Trullidea)

    Meals included: Breakfast
  • Day 4

    At Alberobello (free day or optional ride)

    Spend today roaming around the historic centre, navigating your way through narrow streets, kitsch souvenir shops and tasting local delicacies. Or maybe visit the Museo del Territorio to discover the history of this unique UNESCO World Heritage Site. Alternatively, a circular cycle route (45km/28.5mi - route notes provided) takes you deep into the Itria Valley to visit stunning Locorotondo, with wonderful panoramic views across the valley. Continue on to Martina Franca, a must-see town given its marvellously intact historic centre, beautiful Baroque architecture, and stunning palazzi. (Staying at Trullidea)

    Meals included: Breakfast
  • Day 5

    Alberobello to Pezze di Greco

    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. (Staying at Masseria Salamina)

    Meals included: Breakfast Dinner
  • Day 6

    At Pezze di Greco (free day or optional ride)

    Today you could just relax by the hotel's pool, or cycle to the nearby beach. For the more energetic, a circular cycle ride (48km/30mi - route notes provided) takes you to charming Ostuni whose whitewashed arches and houses are neatly piled like sugar cubes on hills rich in olive groves and vineyards! (Staying at Masseria Salamina)

    Meals included: Breakfast Dinner
  • Day 7

    Pezze di Greco to Monopoli

    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. (Staying at Albergo Diffuso)

    Meals included: Breakfast
  • Day 8

    Monopoli to Otranto

    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 4 star Corte di Nettuno by the harbour in Otranto, close to the old town where there are numerous options for dinner. (Staying at Hotel Corte di Nettuno)

    Meals included: Breakfast
  • Day 9

    At Otranto (free day or optional ride)

    A more 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. (Staying at Hotel Corte di Nettuno)

    Meals included: Breakfast
  • Day 10

    Otranto to Lecce

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

    Meals included: Breakfast
  • Day 11

    Leave Lecce

    Leave Lecce

    Meals included: Breakfast
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.

Essential Info




There are no specific health risks.

Eating and Drinking

In Puglia you will find genuine regional cooking that has strong links to the land and the sea. To give you just a small list of the types of food on offer in Puglia: Bread from the Murge, durum wheat pasta, olives, the pasta delicacy Orecchiette served with a sauce of turnip-tops or fresh tomato and sheep's ricotta-cheese, Cavatelli with pulses, aubergine and parmesan bake, grilled fish and seafood, burrata (soft mozzarella and cream cheese), plus excellent wines. This region is a food lovers paradise and the abundance of delicious vegetables makes it a perfect destination for vegetarians! On this trip there will be many opportunities to taste the best local specialities.


Puglia enjoys a wonderful Mediterranean climate with all year round sunshine and just enough rainfall to ensure that the green is never too far off. Although Puglia covers a large area it is long and narrow - not more than 30km across. This means that you're never far from the sea which has a moderating effect on the weather. Please note that Puglia can be very hot, reaching high 30s in the summer.

Is this trip for you?

Cycling Conditions
Classification: Self-Guided
Average daily distance: 49.75km (25 miles).
No. of days cycling: 9 (3 optional)
Terrain and route: The cycle routes mainly follow tarmac country roads.
Vehicle Support: This is a self-guided trip for those who prefer to cycle independently, but with our assistance to take out the stress of the logistics and planning. We arrange your accommodation, provide you with a map and route notes so that you can cycle at your own pace, while your bags are transported from one hotel to the next.

It is important that you are happy reading maps and following route notes, we make these as accurate as possible and they are regularly checked.

As this is a self-guided holiday there is no group and no leader. There maybe others on the same departure date as you, but you will not be organised together. The routes notes contain a 24-hour emergency assistance telephone number should you need it and in emergencies, the hotels are normally able to dispatch a taxi or pick you up themselves. They may wish to charge for this service.

Call for general departures:
020 8772 3936
Call for tailormade trips:
020 8772 3874
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.



Your accommodation is as varied as the landscape, with each place specially chosen for its unique charm and character. In Monopoli, you stay in characterful rooms set in various locations just 3 minutes from the beach; in Conversano, your beautiful 12th century former court house, with barrel-vaulted ceilings, is just a stone's throw from the elegant Romanesque cathedral; in Alberobello, you cannot fail to be seduced by the authentic trullo houses (limestone dwellings with conical roofs that are the architectural symbol of Puglia), and, in Pezze di Greco, you spend two nights in a beautifully restored 17th century masseria (fortified farmhouse) with lovely pool, open courtyard and 200 hectares of ancient palms and olive trees.

Call for general departures:
020 8772 3936
Call for tailormade trips:
020 8772 3874
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.

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Dates & Prices

An overview of flight options

Exodus is committed to making joining our tours as easy as possible, wherever you live. We generally only block book seats from London, but this certainly does not mean that you need to fly from there. Depending on the route and airlines available, there will usually be various options available for those who want to fly from their local airport.

This page aims to provide a useful overview of the options available to our clients. However, the best flight arrangements should be tailored to your personal requirements, so please contact our Sales team for expert advice.


What kind of options do I have ?

1. We can book for you: Flights from anywhere in the world - not via London  

Depending on the route, this may be direct or via an overseas hub like Amsterdam, the Middle East or elsewhere. On short haul routes there may be direct flights with low cost airlines, charter flights or scheduled airlines. Exodus can book most, but not all, of these for you. The most appropriate airline may be different to that which we use for the group flight from London, but many people now travel on different airlines and meet up with their fellow passengers at the destination.

Pros Cons
  • May be the most direct route
  • Often the extra fare compared to the London flight is minimal.
  • As you will be in the hands a single airline for your entire journey, the airline will be responsible for your bags and your connections.
  • You may not be able to join the group transfers. However, we can usually arrange private transfers, or book your flights to try and coincide with the group transfers. See notes on transfer arrangements below.


2. We can book for you: Connecting flights from your local airport to London

Exodus can book connecting flights to London so you can join the group flight there. Connecting times will be followed according to airline advice, or as requested by clients. There are two types of fares we can use for this option: a 'through-fare' or a 'published fare'.
a) A 'through-fare' is where you will be in the main airline's care throughout. You change planes, but your bags are checked all the way through to your final destination. 

b) A 'published fare' ticket is completely seperate from your onward ticket from London. It is usually cheaper than a through-fare but will need to be paid for and issued as soon as it is booked. This can be a problem if your tour has not yet reached minimum numbers. On 'published fares' neither airline is aware that you have connecting flights, so Exodus is responsible for timing your connection, not the airlines involved. The tickets are also usually non changeable and non refundable.

Pros Cons
  • Depending on the fare type, Exodus or the airline is responsible for flight connections.
  • Through fare tickets can be expensive.
  • On a published fare, tickets must be issued immediately; tickets on published fares can be very difficult to change if onward flight times change; bags are not checked though to your final destination.
  • Published fares are non-refundable.


3. Booking some or all of the flights yourself

You can also book connecting air travel yourself, either to London, or all the way to the start point. There may be certain airlines or routes we don't have access to, so this is always an option. However, if you make your own travel arrangements you become liable for any delays, cancellations or missed connections, and Exodus is not required to offer refunds if you have trouble reaching the start of your trip.

Pros Cons
  • You might find cheaper fares, or routes not available to Exodus.
  • You are responsible for any delays or missed connections, and the cost of the tour is not protected should you miss your flight be cancelled.


 Notes on transfer arrangements

Sometimes it is possible to travel on a different airline to the group flight from London. Where this is the case, we need to think about ensuring you meet up with the group with minimum extra cost and hassle.

  • On certain trips, it is easy to arrive on a different flight and still meet the group at the hotel with time in hand. We can usually arrange private transfers (at extra cost) or offer advice on taking a taxi to the start hotel.
  • On other trips (especially in Europe), the transfer meets the group flight and then travels some distance to the first night's accommodation. Where this is the case, our Sales team will try to arrange flights that arrive before (and depart after) the group. However, we do have to make it clear in your final documentation that if your flights are delayed, the transfer cannot wait for you. While Exodus or our local operators will do what we can to help you reach the start point of the tour, any additional costs must be paid by the client. 


Next steps? 

Call our Sales team on: 0203 733 0698

Email your query: [email protected]

Call us on 020 8772 3936