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Heel of Italy Cycling

Heel of Italy Cycling

1-800-267-3347 Email us
  • Holiday typeSelf-guided cycling
  • Duration10 nights
  • Accommodationhotel-to-hotel
    , and
  • Activity level
  • From $3165per person, tour only
  • Departures
    selected Mons, Weds & Sats from 13 Mar '19 to 26 Oct '19
  • What your holiday price includes
  • 10 nights hotel-to-hotel accommodation in a mix of , and hotels
  • All continental breakfasts and 3 evening meals included
  • Management by your local Headwater-appointed agent
  • GPS route directions and maps
  • RideWithGPS navigation app
  • High quality bikes
  • Standard transfers at the start/end of the trip
  • Optional Upgrades
  • Tandems available
  • Room upgrades and extra nights at selected hotels
  • Excellent choice for
  • Food lovers, wine lovers, flora & fauna, art & history, swimming opportunities, vegetarian meals, couples, coastal routes

Italy: Puglia

Heel of Italy Cycling

  • 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

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 Acaya 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 C18 architecture and known as the 'Florence of the South'.

You'll stay in an excellent variety of accommodation on this holiday, including four **** or ***** hotels and an authentic trullo house in Alberobello! In Conversano your elegant boutique hotel is just a short walk from the mediaeval streets and Romanesque cathedral of this historic town; in Otranto your base is a stylish hotel boasting stunning views over the old town and harbour from roof sun terrace ; while in Lecce you stay in the heart of the beautiful old town in sumptuous ***** hotel, close to the Roman amphitheatre and Baroque palazzi, with the hotel's roof garden offering one of the best views there is over the city.

We're here to help

If you have any questions about this holiday call our sales team on 1-800-267-3347, use our live webchat or email usa@exodustravels.com

Day-by-day itinerary

We're here to help

If you've any questions about this holiday call our sales team on 1-800-267-3347 , or email usa@exodustravels.com

Day 1 - Arrive at Monopoli

Arrive at your hotel in Monopoli. After a welcome briefing there's time to discover the town before dinner. (Staying at Albergo Diffuso, Breakfast only, evening meal at a local restaurant)

Day 2 - Monopoli to Conversano 34km/21.5mi

Today you follow a beautiful coastal route from Monopoli towards the sleepy, inland town of Conversano. On the way you'll have chance to visit the charming, colourful fishing village of Polignano a Mare which is beautifully located, clinging to the limestone cliffs. It's then onward through the pretty village of San Vito, with its tiny harbour full of multi-coloured boats, before arriving in Conversano. (Staying at Relais Corte Altavilla, Breakfast only)

Day 3 - Conversano to Alberobello 39km/24.5mi

Today you'll cycle through the Valle d'Itria, a valley of rolling hills and wooded slopes where the beautiful scent of wild mint and herbs fills the air. Take a break in the small towns of Putignano and Noci, with their typical whitewashed houses and narrow alleyways. It's then off to UNESCO-recognised Alberobello, filled with the quirky Trulli houses . (Staying at Trullidea, Breakfast only)

Day 4 - At Alberobello

Take some time to explore the narrow streets of historic Alberobello. Browse the quirky souvenir shops or sample the local cuisine in one of the bars or restaurants; perhaps learn about the town's history at the Museo del Territorio. If you fancy cycling, a circular route (45km/28.5mi - route notes provided) takes you into the heart of the Itria Valley and spectacular Locorotondo, with its 360 degree views of the valley. The town of Martina Franca lies a little further ahead - continue on to discover its stunning Baroque architecture and palazzi. (Staying at Trullidea, Breakfast only)

Day 5 - Alberobello to Pezze di Greco 49km/30.5mi

This morning you'll follow winding country lanes before a long downhill stretch takes you towards Capitolo (enjoy panoramic views of the Adriatic coastline on the way), ending in a beautiful collection of almond and olive orchards, vineyards and vividly coloured fields full of peppers and tomatoes. (Staying at Masseria Salamina, Half Board)

Day 6 - At Pezze di Greco

The choice is yours today. You could head to the local beach or simply spend time unwinding by the hotel pool. If you fancy something a bit more challenging, we provide route notes for a circular cycle ride (48km/30mi) which takes you to Ostuni with its dazzling whitewashed houses sitting beautifully above olive groves and vineyards. (Staying at Masseria Salamina, Half Board)

Day 7 - Pezze di Greco to Monopoli 37km/23.5mi

Follow an easy route to the Adriatic coast, passing the vibrant fishing village of Savelletri, a perfect stop for a tasty lunch or traditional Italian coffee. You'll cycle past the archaeological ruins of Egnazia, the site of a Greco-Roman town which dates back to 4BC, before reaching the pretty seaside town of Monopolil. Tonight you can choose from a wonderful selection of restaurants in the old town. (Staying at Albergo Diffuso, Breakfast only)

Day 8 - Monopoli to Otranto 42km/26.5mi

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, Breakfast only)

Day 9 - At Otranto

A free day in Otranto today, or an optional 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, Breakfast only)

Day 10 - Otranto to Lecce 37km/23.5mi

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

Day 11 - Leave Lecce

Please note: This tour has been given a 1 Bike + rating based on ascents/descents and distance; the cycling may feel harder over the hotter months.

Where you stay

During your holiday you stay at the following hotels. If you'd like to extend your time at any of these or, if you'd like to enhance your stay with an upgraded room, just let us know at the time of booking. If you'd like to keep your bikes with you for any extra nights we can arrange this for you for just £25 per adult per day and £18 per child per day.

To find out more call our sales team on 1-800-267-3347, use our live webchat or email usa@exodustravels.com

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Albergo Diffuso Monopoli, Monopoli

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This property is 3 minutes walk from the beach. Set in various locations around the historical centre, just a stroll from Monopoli's seafront and its beautiful beaches, Albergo Diffuso Monopoli offers elegant rooms, all air-conditioned rooms either have a terrace or balcony.

Accommodation has exposed Tuffo-stone walls and quality furniture. There is free WiFi, flat screen TV, air conditioning and a private bathroom with bath or shower.

Breakfast in the hotel's central cafe and dinner will be in a good local restaurant.

Room upgrades: Suite.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Relais Corte Altavilla, Conversano

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The 4-star hotel Corte Altavilla Relais & Charme is located right in the historic centre of Conversano, just off one of the main squares - Piazza Conciliazione. The hotel is in an old medieval building with inner courtyard that once served as an old medieval courthouse for the town.

Following major renovation works in 2002 the hotel opened as an elegant four-star boutique hotel with 32 elegant rooms and appartments, each with its own personality and charm, with white stone walls, wrought iron furnishings, wooden-beams and vaulted ceilings.

All rooms are equipped with modern amenities including: air-conditioning, satellite-TV, direct-dial telephone, safe, Internet and mini-bar/fridge.

Room upgrades: Junior Suite .
The Junior Suite has charming furniture with a living room and panoramic view.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Trullidea, Alberobello

A unique and authentic experience staying in a trulli, a traditional 15th Century Apulian stone building with conical roof.

Each trulli house is made up of a double bedroom, small bathroom with shower and living area with sofa and small kitchenette.

The trullis are located in the centre of historic Alberobello, a UNESCO world heritage site, within walking distance of cafes, restaurants and shops.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Masseria Salamina, Pezze di Greco

Swimming Pool IconHair dryer iconNEARBY:

Masseria Salamina is a large 17C fortified farmhouse, set in 173 acres of rich agricultural farmland. The property is surrounded by orchards of secular olive trees that are up to 400 years old, used in the production of their own high quality, extra virgin, olive oil.

Inside the masseria, there's a large and welcoming restaurant where you can taste specialities of sumptuous Southern Italian cuisine, served in the suggestive atmosphere of the open-air courtyard.

The rooms here are simple yet comfortable and with all the necessary amenities and have been created out of the conversion of the masseria's outbuildings. The common areas comprise of the meeting hall, bar, lounge & TV room and the outdoor swimming pool with views reaching across to the sea.

Room upgrades: Farmhouse Suite, Double Room Superior, Junior Suite or Junior Suite Deluxe .
The farm House suites are spacious and comfortable, pproximately 50m2, composed of a double room, living room with single bed, wide bathroom with bathtub, and a kitchen. They are located in the south-east wing, of more recent construction but always adjacent to the Masseria, all with a wonderful view and with their own outdoor space. The Superior Room is in the Manor wing of the Masseria, on the 1st floor, the owner's house since the 17C, it has valuable antique furniture, with marble bathroom, it has a hall and an indoor balcony with view. The Junior Suite is in the Manor wing of the Masseria, on the 1st floor, the owner's house since the 17C, it has valuable antique furniture, with marble bathroom and Jacuzzi. Deluxe Junior Suite is in the Manor wing of the Masseria, on the 1st floor, the owner's house since the 17C, it has valuable antique furniture, with marble bathroom, it has a hall and a private balcony with view. The Superior Suite is in the Manor wing of the Masseria, on the 1st floor, the owner's house since the 17C, it has valuable antique furniture, a living room with fireplace and balcony, and marble bathroom with Jacuzzi and showerbox.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Corte di Nettuno, Otranto

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This property is 10 minutes walk from the beach. Once a farmhouse, Corte di Nettuno now offers modern rooms and 2 rooftop terraces overlooking the harbour.

Throughout the hotel, you will find a unique marine design with sea-themed mosaics, shipping maps, and other nautical objects as decor. Your room features a flat-screen TV, air conditioning, and free internet access.

The restaurant at Hotel Corte Di Nettuno is a great place to sample dishes and wines from the Puglia region. It offers a large buffet breakfast, and all meals can be enjoyed out in the large courtyard. Alternatively you can walk into the centre of town (10 min ) and try one of the cheap local fish restaurants.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Resort Hotel Risorgimento, Lecce

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Featuring a roof-top restaurant with panoramic views, the Risorgimento Resort is located in Lecce's Baroque historic centre. It offers free WiFi throughout, large modern rooms, and a relaxing spa.

Rooms are air conditioned and come with a minibar and satellite TV. Each has a marble bathroom with bathrobes and slippers. The attentive staff provide a continental buffet breakfast. The 3 restaurants offer both Salento flavours and classic Italian cooking. Alternatively there are plenty of good restaurants nearby. Drinks and snacks are available all day at the Janet Ross Bar.

The health club offers a Turkish bath and multisensory shower. Massage and beauty treatments are also available.The hotel doesn't have a pool but there's everything else! Its even got it's own golf course (3km away)!

Piazza Sant'Oronzo is just 100 yards from Risorgimento Resort . The Cathedral is a 5-minute walk away.

Room upgrades: Deluxe Double, Executive, Junior Suite or Garden Suite.


Transfers included from Bari airport at 14:45, and back to Brindisi airport at 09:30.

Please call our sales team on 1-800-267-3347 or email usa@exodustravels.com to arrange connecting flights.


Here at Headwater we thrive on feedback from our customers. It's the only way we can continue to develop, and where necessary improve, our services and ensure our holidays continue to be the best they can be. However, as this is a relatively new holiday, we don't yet have any customer reviews available.

Dates and prices

You can be confident that our pricing includes all the standard requirements of your holiday and many additional extras. Always ensure that you are comparing like for like when booking your holiday. Find out about The Headwater Price Promise to ensure you're getting the very best value for money.

For further details, or to check availability, speak to our sales team on 1-800-267-3347 or complete our holiday enquiry form (we'll contact you at a time that's most convenient for you).

To enquire about this holiday, or for further information, call our sales team on 1-800-267-3347 or complete our holiday enquiry form.

  • Mar
  • Apr
  • May
  • Jun
  • Aug
  • Sep
  • Oct
Mar 2019Tour only Availability
13th Mar US$3165 Check availability
16th Mar US$3165 Check availability
18th Mar US$3165 Check availability
20th Mar US$3165 Check availability
23rd Mar US$3165 Check availability
25th Mar US$3165 Check availability
27th Mar US$3165 Check availability
30th Mar US$3165 Check availability
Apr 2019Tour only Availability
1st Apr US$3165 Check availability
3rd Apr US$3165 Check availability
6th Apr US$3165 Check availability
8th Apr US$3165 Check availability
10th Apr US$3165 Check availability
13th Apr US$3165 Check availability
15th Apr US$3165 Check availability
17th Apr US$3195 Check availability
20th Apr US$3195 Check availability
22nd Apr US$3195 Check availability
24th Apr US$3195 Check availability
27th Apr US$3195 Check availability
29th Apr US$3195 Check availability
May 2019Tour only Availability
1st May US$3355 Check availability
4th May US$3355 Check availability
6th May US$3355 Check availability
8th May US$3355 Check availability
11th May US$3385 Check availability
13th May US$3385 Check availability
15th May US$3385 Check availability
18th May US$3385 Check availability
20th May US$3385 Check availability
22nd May US$3385 Check availability
25th May US$3385 Check availability
27th May US$3385 Check availability
29th May US$3385 Check availability
Jun 2019Tour only Availability
1st Jun US$3385 Check availability
3rd Jun US$3385 Check availability
5th Jun US$3385 Check availability
8th Jun US$3385 Check availability
10th Jun US$3385 Check availability
12th Jun US$3385 Check availability
15th Jun US$3385 Check availability
Aug 2019Tour only Availability
5th Aug US$3385 Check availability
24th Aug US$3385 Check availability
26th Aug US$3385 Check availability
28th Aug US$3385 Check availability
31st Aug US$3385 Check availability
Sep 2019Tour only Availability
2nd Sep US$3385 Check availability
4th Sep US$3385 Check availability
7th Sep US$3385 Check availability
9th Sep US$3385 Check availability
11th Sep US$3385 Check availability
14th Sep US$3385 Check availability
16th Sep US$3335 Check availability
18th Sep US$3335 Check availability
21st Sep US$3335 Check availability
23rd Sep US$3335 Check availability
25th Sep US$3335 Check availability
28th Sep US$3335 Check availability
30th Sep US$3335 Check availability
Oct 2019Tour only Availability
2nd Oct US$3165 Check availability
5th Oct US$3165 Check availability
7th Oct US$3165 Check availability
9th Oct US$3165 Check availability
12th Oct US$3165 Check availability
14th Oct US$3165 Check availability
16th Oct US$3165 Check availability
19th Oct US$3165 Check availability
21st Oct US$3165 Check availability
23rd Oct US$3165 Check availability
26th Oct US$3165 Check availability

The prices quoted for each individual departure supercede those published in our current brochures. Air prices are subject to change and we advise early booking to obtain the best prices. Please see our Planning your holiday and What's included in the price? pages for additional information.

Holiday details

This holiday is unsuitable for children.

Holiday type
Self-guided cycling Managed locally by Headwater appointed agent.

selected Mons, Weds & Sats from 13th Mar 2019 to 26th Oct 2019, for 10 nights.

All continental breakfasts and 3 evening meals included

It is possible to hire tandem bikes for this holiday at a supplement of £305 per bike. As these are available on a first come first served basis, we recommend early booking to avoid disappointment.

Other details
Airport transfers are subject to at least 2 people (in total) booked on each departure.

Tailor-made travel

Tour only
Transfers included from Bari airport at 14:45, and back to Brindisi airport at 09:30.

How to book

For further details, or to check availability, speak to our sales team on 1-800-267-3347 or complete our holiday enquiry form (we'll contact you at a time that's most convenient for you).

To enquire about this holiday, or for further information, call our sales team on 1-800-267-3347 or complete our holiday enquiry form.

We are ATOL registered We are an ABTA member
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