Home > Riding Italy’s Boot: From Alberobello to Lecce

Riding Italy’s Boot: From Alberobello to Lecce

Les trulli d\'Alberobello qui sont classés au patrimoine mondial de l\'UNESCO 5
The trulli of Alberobello Cycling past Apulian farms The white city of Ostuni The coastline of Gallipoli Typical Apulia country lane
Les trulli d'Alberobello qui sont classés au patrimoine mondial de l'UNESCO

Riding Italy’s Boot: From Alberobello to Lecce

  • Level
  • PriceFrom 735 euros
  • DAY6 nights / 7 days

More info: Receive detailed hotel list, bike specs, and route description

More infos BOOK NOW !


Nestled in the heel of Italy’s ‘boot’, Apulia is one of the country’s best-kept secrets, boasting a stunning coastline, rich agricultural traditions, historic towns, and fantastic cycling along virtually traffic-free roads. On this road bike tour from Alberobello to Lecce, you will experience the region from its hilltops to its beaches, from countryside to coast. Daily rewards of fine wine, seafood, and traditional Puglian cuisine serve as a complement to the postcard-worthy views you’ll enjoy from the seat of your bike.


The trulli of Alberobello, Otranto’s exquisite mosaic floors, and the beautiful old town of Gallipoli are just a few of the highlights that will keep your heart in Apulia long after you return home.


An optional 2-night extension from Lecce to Polignano a Mare is available upon request.


D1Arrival in Alberobello

You won’t meet with our local representative until tomorrow morning, so you have the whole day to arrive in Alberobello, one of Italy’s most unique towns. You will soon discover that everything here revolves around trulli, the white-washed conical-roofed houses that give the town its UNESCO World Heritage Site designation and continue to be a fascination for visitors. We highly recommend giving yourself time to explore this picture-perfect town!

D2Alberobello - Manduria Via Martina Franca 77 km/48 miles, 575 meters/1,880 ft of climbing; Via Ostuni 91 km/57 miles, 770 meters/2,525 ft of climbing

You’ll start your adventure with a leisurely ride today, warming you up for the hills to come! Heading out of Alberobello, follow the trulli and olive trees as you pedal. If you opt for the longer route, an extra 24 km (15 miles) will take you to the “White Town” of Ostuni, where you can enjoy dramatic views of the coast from its hilltop cathedral. The surrounding fields seem to grow ever vaster as you descend, cycling towards your destination for the day. Rejoining the shorter route in Ceglie Messapica there are plenty of lunch spots to rest in. Arriving in Manduria, you can visit a famous well that was mentioned by Roman author Pliny the Elder...over 2,000 years ago! At dinner, savour the fruits of the land, accompanied by a glass of typical full-bodied Primitivo di Manduria wine.

D3Manduria - Gallipoli 69 km/43 miles, 385 meters/1,265 ft

On this day, you’ll be cycling along quiet secondary roads, tracing the ‘heel’ of Italy’s boot and counting the ancient watchtowers that dot the coast. For birdwatchers, the Salina dei Monaci is a must-stop -- a salt lake that is now a natural reserve and a favourite of migratory birds, from swans to flamingoes. Rest for lunch at Porto Cesareo, where the long sandy beaches and turquoise sea will make it very difficult to get back on your bikes!


When you do arrive in Gallipoli, you will find many rewards for your willpower. Explore the island-based old town, with sights including the 13th-Century castle, Greek Fountain, and an olive oil museum located in an old olive mill. If you’re lucky, you might even catch a breathtaking sunset over the Ionian Sea to cap it all off.

D4Gallipoli - Leuca 72 km/45 miles, 535 meters/1,755 ft of climbing

Passing (and likely pausing) by the gorgeous Baia Verde beach on your way out of Gallipoli, you’ll follow the coast until Torre Sinfono, where you’ll then turn inland. A steady ascent will take you through quiet country roads and national parks, as well as the towns of Ugento, Acquarica del Capo, and Specchia. You’ll then pedal back towards the coast, heading downhill for around 14 km (9 miles) along sunbaked fields and low stone walls.


In Leuca, be sure to visit its monumental staircase and iconic lighthouse (the second most important in Italy.) The beautiful waters in front of you is where the Ionian and Adriatic seas meet, and you can’t go wrong with any seafood dish on the menu.

D5Leuca - Otranto 70 km/44 miles, 785 meters/2,575 ft of climbing

From Leuca, you’ll follow the coastline north to Otranto, the ocean spray helping to keep you cool. Along the way, you’ll pedal past gullies, grottos, old towers, and beaches, as well as charming seaside towns. If you opt for the longer version, a 30 km (19 mile) deviation inland will introduce you to small, historic towns such as Gagliano del Capo, Tricase, and Corsano before returning to the coast.


Around kilometer 46 (mile 29), make a stop at Porto Badisco, where the wall art of their Deer Cave is known as "the Sistine Chapel of prehistory." These paintings date back to the Neolithic period, around 7,000 years ago! Shortly afterwards, you’ll arrive in Otranto, which is famous for its intricate mosaic floors from the 1100s as well as its Archdiocese, a church where the bones of 813 martyrs are celebrated. For an attraction a little less macabre, the Otranto Castle has a museum you can tour, as well as a fantastic panoramic terrace from which to view the city.

D6Otranto - Lecce 79 km/49 miles, 455 meters/1,495 ft of climbing

On today’s route, you’ll head inland towards the Grecia Salentina, home to the Griko people (an ethnic Greek minority). Then, you reach the small coastal village of Conca Specchiulla, from where you’ll spend the remainder of the ride pedaling north along the picture-perfect turquoise coast. Like the last couple of days, you’ll have dozens of beaches and caves to stop and explore along the way!

The final 20 km (12 miles) of your ride will have you climbing away from the coast and into Lecce, where you can enjoy the rustic local cuisine and explore the city’s incredible jewels at your leisure. Reminiscent of Rome or Florence, Lecce is home to Roman ruins, palaces and castles, theatres and opera houses, and monuments to heroes and their heroic deeds.

D7Departure or Lecce - San Vito dei Normanni (Optional Extension) 65 km/40 miles, 300 meters/985 ft of climbing

Day 7:


After breakfast, you are free to depart Lecce at your leisure or continue on our optional extension to Polignano a Mare. Extra nights can be arranged upon request.


Optional Extension Lecce - San Vito dei Normanni

If you are feeling a little sore after several days in the saddle, today’s ride and destination are guaranteed to provide sufficient delights and distractions! Quiet rural paths and roads will lead you from Lecce into an agricultural heartland, with fields, orchards, and vineyards abounding. Villages and towns dot your route, like Mesagne (46 km/29 miles), where you can go back in time at the archaeological museum, housed in an 11th-century castle.

A short climb will bring you to the hilltop perch of San Vito dei Normanni, where an early arrival will leave you with plenty of time to enjoy this beautiful town. Marvel at the Castle of Dentice Frasso and its ancient tower, overlooking the main piazza; experience a different side of history at the Rural Museum; and visit the town’s many churches, including the integral Santa Maria della Vittoria. You’ll eat and drink well at dinner too, tasting the local wines and traditional specialties including stuffed eggplants, lamb skewers, almond cupeta cakes.

D8Optional Extension: San Vito dei Normanni - Polignano a Mare 70 km/44 miles, 450 meters/1,475 ft of climbing

The adventure closes with a joyful return to the coast today, as you wind your way towards beautiful Polignano a Mare and your last stop on this extended cycling holiday of Apulia. Take in quaint fishing villages and views of the sea while you pedal, as well as the “White Town” of Ostuni (if you missed it on Day 2). Before you arrive in Polignano, let your bikes rest for a while in nearby Monopoli, a gorgeous seaside town with some interesting sites that include the Rock Church of St. George and the pentagonal Castle of Charles V.


Polignano itself is known as the “Pearl of the Adriatic”, and for good reason! Its whitewashed buildings built upon cliffs is as picture-perfect as it gets. Visit its popular caves or enjoy a croissant in the historical centre, where traces of the town’s Arab, Byzantine, Spanish, and Norman past still exist, including the remains of the four watchtowers that once guarded the ancient town.

D9Optional Extension: Departure

From Polignano, it’s about a 40-minute train ride to Bari, from where you can catch another train or a plane to your next destination.

Booking & Prices

  • Option A
  • 6 nights in guesthouses “of character”

  • 735 euros per person in January through April; October through December. Single supplement is 275 euros
  • 895 euros per person in May, June, and September. Single supplement is 325 euros
  • 1,155 euros per person in July. Single supplement is 375 euros
  • Option A+
  • 6 nights in 4-star hotels and deluxe guesthouses

  • 1,075 euros per person in January through April; October through December. Single supplement is 375 euros
  • 1,365 euros per person in May, June, and September. Single supplement is 455 euros
  • 1,655 euros per person in July. Single supplement is 575 euros

These prices include:

  • 6 nights’ accommodation as described above (ask us for extension prices)
  • Daily breakfast
  • Meeting with our local representative
  • Luggage transfers
  • Marked maps and/or cue sheets and route notes
  • Tourist information
  • Pre-loaded GPS unit
  • Assistance if necessary (you will be provided with our local rep’s mobile number)
  • Service charges and most taxes

These prices do not include:

  • Nominal city taxes, to be paid in cash directly at each hotel (from 1-4 euros per night depending on the season, the town, and the accommodation types)
  • Expenses of a personal nature
  • Travel insurance
  • Bicycle rentals. Hybrid bikes are available at the rate of 120 euros. Aluminum racing bikes are available at the rate of 180 euros. E-bikes are available at the rate of 225 euros. (Extension rates for bicycle rentals are 130, 195, and 250 euros respectively). All prices are inclusive of the drop-off fee.

Suggested Cycling Trips