Italy Self Guided Biking / Puglia

Tour Dates: Mar-June & Sept-Nov
You can begin your trip any day of the week except Sunday.

This is a beautiful self-guided cycling trip through the region of Puglia, Italy, which lies in the heel of the boot, along the sun-drenched Adriatic Sea. Puglia offers access to the freshest seafood, crowd-free open spaces, irresistible desserts and pastries, distinct wines, and the 50 million olive trees that make Puglia the world’s leading producer of olive oil. Our exceptional cycling routes pass through fishing villages, country lanes, ancient olive groves and vineyards, hidden coves and golden beaches. A real highlight is a trip to the UNESCO World Heritage Site of Alberobello with its ancient trulli houses.

This self-guided tour is a fully organized vacation for the independent traveler who wants the freedom to cycle at his or her own pace. You’ll have complete support behind the scenes. Our Italy representative will meet you at the beginning of your tour for an orientation. You will receive a packet with detailed route instructions, maps, suggestions for sites to visit along the route and emergency support phone numbers. You can take a spontaneous detour and always feel secure that your hotel room will be waiting for you. You may choose to bring your own bike or rent a bike. If you choose to rent a bike, our representative will bring the bikes to you on the first day. You will be able to travel at your own pace without a guide or support vehicle to hurry you along or to slow you down. Your luggage will be transported each day to the next accommodation, which will be reserved and prepaid. You don’t need to worry, as emergency support is just a phone call away.

Multiple Tour Options to choose from. We have our standard 7-Day tour, or you could choose the longer 9-Day Version!

2023 7-Day Tour Cost: €1825 Euros 2022 9-Day Tour Cost: €2450 Euros

pp double occupancy
  • 7-Day Single Supplement: €475 Euros
    • 7-Day Bike Rentals: Hybrid bike / €220 euros, Electric bike / €400 Euros, Road bike / €365 Euros
  • 9-Day Single Supplement: €870 Euros
    • 9-Day Bike Rentals: Hybrid bike / €280 euros, Electric bike / €500 Euros, Road bike / €450 Euros
7-Day Tour Price Includes:
  • 6 nights lodging
  • 6 breakfasts
  • 1 dinner
  • Luggage Transfers
  • Welcome Drink & Snack
  • Maps and route notes to download to your phone
  • Dining suggestions
  • Emergency phone numbers for our Italian staff support
9-Day Tour Price Includes:
  • 8 nights lodging
  • 8 breakfasts
  • Hybrid Bike Rental
  • Luggage transfers
  • Train Ticket from Fasano to Squinzano and shuttle back to Otranto
  • Welcome Drink
  • Thorough Bike Fitting & Orientation
  • Exceptional, detailed maps and route notes
  • Local city maps and dining suggestions
  • Emergency phone numbers for our Italian staff support
Optional Add-Ons:
  • Shuttles from/to Bari or Brindisi airport or train station
  • Room upgrades
  • Extra day of cycling to Lecce
  • Walking tour of Matera, Alberobello, or Lecce
Prices Do Not Include:

International flights, restaurant lunches, airport transfers, beverages, bike rentals

Tour Difficulty

This tour is rated easy to moderate difficulty over rolling terrain. There are a couple days that have longer options and we will provide transfers so that you can expect 35 – 65 km of riding each day.

  • Difficulty: Rolling hills and flat
  • Road Conditions: Smooth & Paved
  • Recommended Bike: Hybrid or Road or Electric

Tour Highlights

  • Sun-drenched beaches of the Adriatic
  • Panoramic vistas
  • Archaeological treasures
  • World Heritage sites
  • Italy’s most savory cuisine and regional wines


7-Day Itinerary:

Day 1

Arrival on your own to your hotel in Polignano a Mare. If you choose, we can provide optional shuttles from and to the Bari or Brindisi airport or train station for an additional fee. You will have a briefing and we will custom fit you to your bikes. We will provide you with exceptional maps and route notes to help you navigate your way along the countryside and find special hidden gems to stop, explore, and dine. Your lodging is in the beautiful cliff top town of Poligano a Mare. Dinner is included at the hotel this evening, but we recommend you take a stroll around town to sample the famous ice-cream and granite of Polignano!

Day 2: Cycling: Polignano-San Vito –Conversano –Turi loop Approx 60km

For your first ride, you will embark on a charming route along stunning the Adriatic coastline from Polignano a Mare to the picturesque village of San Vito, with its multi-coloured boats moored up in the tiny port, You will continue through the olive groves to the sleepy, beautiful town of Conversano, set in the hills with its rambling alleyways and sun-baked piazza dominated by the Norman castle and Romanesque cathedral. Our journey then takes us up to Turi, the cherry capital of Southern Italy – if you are here in May you can enjoy an abundance of fresh ruby cherries to help you on your ride. To finish there is a gorgeous descent looking out across the Adriatic Sea and back into vibrant Polignano, wow what a day!

Day 3: Cycling: Polignano-Castellana Grotte-Putignano-Alberobello Approx 60km

Today, you will leave Polignano and climb to the stunning cave complex of Castellana Grotte. Tours in English are held at 11am and are well worth the time to see the intricate stalactites and stalacmites. From Castellana you pedal through rolling countryside savouring the sweet aroma of mint that grows by the roadside and stop to enjoy the little towns of Putignano and Noci, with their characteristic whitewashed houses and narrow alleyways. Our destination is Alberobello with its plethora of unique trulli houses, the most famous architectural symbol for which this region is known. Here your lodging for the night is in your very own trullo so you can enjoy the magical experience of sleeping under the iconic cones.

Day 4: Cycling: Alberobello-Cisternino-Ostuni 39km

Today, you will leave the lovely town of Alberobello and cycle to Ostuni, pedaling down beautiful scenic country lanes lined with weathered stone walls. After progressing over some rolling hills to the edge of the plateau, you will enjoy panoramic views of the Adriatic coastline and the lower fertile plains. As you progress to Cisternino, one of the most lovely and chic hilltop towns in Puglia, you will soak in sweeping views of the Itria Valley below and see firsthand why this town is starting to gain some serious international repute. We will then ride past olive groves and rock-strewn fields to the stunning “città bianca” or “white city” of Ostuni. Your home for the next two nights will be the lovely, situated in the pastoral community with old-time charm.

Day 5: Cycling: Ostuni-Carovigno-Ceglie Messapica-Ostuni 42Km

Today you embark on a circular bike ride to Carovigno and Ceglie Messapica. This ride will take you along rolling country roads lined with ancient stone walls within the fertile Itria Valley. Along the ride, we recommend you stop at the sanctuary of St. Maria del Belvedere, a beautiful historic landmark that must be
viewed. Next, you will cycle toward Ceglie Messapica, which is a lovely town on a hill, and is protected by a 5 kilometer wall that surrounds this cherished town. Within the town of Ceglie Messapica is the Castle of the San Severino, which is very famous for “enogastronomic” events, making it a global food and wine capital.

Day 6: Cycling: Ostuni- Torre Canne- Savelletri- Egnazia – Monopoli Approx 40 km

Today you will enjoy panoramic views of the Adriatic coastline and the lower fertile plains. From here we head through the tiny towns until we reach the picturesque coastal town of Monopoli and your accommodation for the night, the 16th century Palazzo Indelli in the very heart of the old town. A further optional loop takes you back to the coast and to the fascinating Bronze Age and Roman Ruins of Egnazia.

Day 7:

After breakfast, you will depart for your flight home or next destination.


9-Day Itinerary:

Day 1

Your adventure begins in the UNESCO site of Matera, the city of artists. Only recently seen by foreign eyes after a period of abandonment, Matera is a UNESCO World Heritage site and home to the fascinating “Sassi”. The sassi have been restored in recent times and are now used as shops, homes, restaurants, and hotels. Discover the intriguing secrets and stories of this extraordinary town as you walk around and explore the area. Our Italian representative will meet you for a bike fitting and tour orientation.

Day 2: San Giuliano Loop 45km/28mi and Montescaglioso Loop 60km/37mi

Today you have two options. The San Giuliano is the shorter where you head to the San Giuliano oasis, under the protection of the Italian branch of the World Wildlife Foundation. The preserve covers about 1000 hectares and includes the San Giuliano Dam (which was built in the 1950s and was Basilicata’s first artificial basin) as well as the Bradano River Ravine.

The other option is to Montescaglioso. The route leads to Montescaglioso, home of a powerful and prestigious abbey which once controlled a huge swath of surrounding land. The major climb into Montescaglioso is worth it for the opportunity to visit this enchanting little village where time seems to have
stopped. The ride back to Matera can be challenging.

Day 3: Cycling: Matera – Alberobello (70km)

Your ride today takes in stark terrain, with wide open spaces and lots of farm land. After approx. 15km you will leave the region of Basilicata and enter Puglia. The route takes you through Gioia del Colle where we can visit the impressive Norman Castle which dates back to the 9th century. Alternatively you can bike to a prestigious winery. From there you head towards Noci, a well-heeled town known for its mushroom festival. As you head deeper into the area known as the Itria Valley you will arrive at the Trulli Capital, Alberobello and check into your next lodging.

Day 4: Cycling: Alberobello-Locorotondo-Martina Franca- Pezze di Greco approx. 45 km

This route goes deep into the Itria Valley and includes some the oldest and most beautifully “trullo” countryside in the whole of Puglia. This morning, approximately 7km outside of Alberobello you can stop at a local farm for an insider’s look at burrata cheese-making. This fresh cheese is the wildly indulgent cousin of mozzarella cheese and is native to Puglia. During your visit you will have the opportunity to sample the cheese made this morning – you will never taste fresher than this! Afterwards you will head straight to Martina Franca for lunch – a must-see town for its marvelously intact historic center, beautiful Baroque architecture, and stunning palazzi; a jewel splendidly positioned on the hillside with wonderful panoramic views across the Itria Valley. You will spend 2 nights at this special Masseria.

Day 5: Cycling: Savelletri-Cisternino-Ostuni loop (62km)

Today you can choose to make this a rest day or ride a loop. If you choose to ride, the morning begins with a lovely climb into the chic and beautiful hilltop town of Cisternino, where you will enjoy sweeping views of the Itria Valley. You will have time for a coffee or gelato to recharge your batteries before continuing your lovely ride along the ridge to La Città Bianca (the white city) of Ostuni, a stunning hilltop jewel with breathtaking sea views. In Ostuni, you will have many options for a delicious lunch including the opportunity to sample one of many preparations of the ubiquitous orecchiette (little ear- shaped) pasta.

Day 6: Cycling: Squinzano-Otranto (70km)

After a lovely last breakfast at the Masseria, you will head to Fasano station and get the train to Squinzano, the starting point for an amazing day of cycling through the stark and contrasting beauty of the Salento area, home to Puglia’s best wines. With the warm sun overhead and the sea almost always in view, this is one of the coolest days to be on a bike! You can stop for a swim at one of the amazing beaches along the route before hopping back on our bikes and continuing your journey. You can also stop in the famous castle city of Acaya for a walk around and local lunch. Your destination is the ancient city of Otranto, a must-see that’s one part beach resort, one part Middle Eastern, many parts Italian, and every part enjoyable!

Day 7: Cycling: Otranto-Santa Maria di Leuca (55 km)

Breathtaking sea views, natural hot springs, hills, and pine forests make this one of Italy’s most memorable rides. You will ride down to Santa Maria di Leuca, which the Romans called Finnibus terrae (the end of the earth). Here you can stand on the southernmost point of Puglia and gaze out to the inviting sea. We will arrange a shuttle back to the hotel.

Day 8: Cycling: Otranto to Lecce (40  km)

Today, you will head down to the wonderful town of Lecce, known as the Florence of the South. You will find the terrain is mostly flat, passing among endless olive orchards. Your ride will lead you through the small enchanting villages of Borgagne, Melendugno, Castri’ di Lecce e Lizzanello… all villages in which time seems to have stopped. So, be sure to stop and smell the olives. Your final hotel destination, is a special accommodation in Lecce. You will have plenty of time to explore the city in the afternoon.

Day 9: Departure

Tour ends after breakfast. You will depart for your flight home or next destination. We are sure that your time in this region will have changed your life for the better, as it has all of ours!