We meet you in Matera in the early morning to ride across the open wheat fields and into the trulli laden countryside. Our ride starts from the ravine overlooking Matera´s gorge and continue down along the quiet scenic stone fenced pathways rich in vineyards, oak saplings, and fruit trees.

You will have the choice of a short or long route and at the end of your ride a we visit the largest network of underground grottoes in Italy then transfer to Alberobello, a UNESCO Heritage site and declared national monument. Alberobello is a fairytale-like village of gnome-like structures that is truly memorable. The ancestors of our dear friends and host, Dino and Antonella, have resided here for over 500 years. They provide us with not only great hospitality, but for each of us a trullo-house during our two-day stay. The trullo seen above is an unusual stone house circular in shape with whitewashed walls and a gray slate cone-shaped roof often marked with mysterious symbols.

On day two we loop through a rural countryside that passes colorful fields filled with poppies, wild flowers and fairy tale landscapes that demand you reach for your camera. We drop down into the land of dairy & wheat farmers and horse breeders. Here the terrain continually varies as you get a chance to sample long rolling stretches, and some short climbs. Once back into Alberobello we tour a local olive oil producer who still makes olive oil the traditional way using a stone press for the locals as well as with modern equipment for commercial production. We may also stop at a local winery for a tour and wine tasting of the regional wines they produce that includes the excellent “Primitivo” and Negro Amaro which are sure to impress.

Lodgings: A unique and fairytale-like trullo in the heart of the historic trulli village

Our route takes into the tiny hill towns of Locorotondo and Cisternino which marks the boundary to the Valley of Itria. It is from here the trulli are last seen. The origin of the Trulli is uncertain, yet it is felt that the cone shape is of Eastern inspiration and may have been adopted in Puglia because it is easy to construct. Others claim that religious or magical reasons have led to their adoption as religious and astrological symbols are often painted on the roofs. As we ride within the Valley of Itria we get a chance to examine these theories up close as we enjoy one bellavista after another before a 10-km downhill cruise through pine lead to the blue green waters of the Adriatic Sea. A quick dip is the ideal way to clean up for a delicious sit down lunch.

You have the option to stop at the significant ruinous site of Egnazia where archaeologists have uncovered remnants of early Greek and Roman civilizations and then meet up with those who wish for a more challenge. Both rides then lead to Ostuni via the ancient olive groves that are sure to mesmerize the viewer and leave one with the feeling that any minute one of them will speak; as if from the "Land of OZ".

Whitewashed Ostuni, a town of pre-historic origin, has survived the ages and retains the most typical of Apulian architecture in accordance with its historic growth. It is felt that through the ages it has succeeded in staying in perfect balance with the surrounding countryside. From the moment we approach from miles away, to the moment we enter the historic town center; it would be hard to argue against this observation.

Lodging: A beautiful 4-star hotel in the historic center.

From Ostuni we ride across the long flat valley filled with vineyards and towns whose roots go back to Puglia's original inhabitants of 3000 B.C., the Messapi. We visit Oria, once capital of the Messapi then a major Roman trading center on the Apian Way, and evolving into an important Jewish colony. Explore the triangular castle and an old town center loaded with architectural attractions as we cross the plains to the incomparable, Lecce.

Lecce has often been described as a Baroque Jewel, and jewel it is. This lively town offers us a chance to enjoy an active evening within the unrivalled architecture of soft pink local stone used to build everything from the piazzas and town gates to the numerous churches that adorn this city of unparalleled beauty. During our first day off the bike we enjoy an extensive private city tour that not only examines the fine Baroque structure, but stops by the renowned papier-mâché studios. You are then free to explore more of the city on your own or cycle to the sea for a comfortable swim.

The following day we ride past the ruins of a castle from the Messapi period and through the pine forest surrounding the Alimini Lakes. The Alimini Grande to the north is in contact with the Adriatic and is therefore salt water, while the Alimini Piccolo connected on the south end is nourished by a spring and is therefore fresh water. The landscape around both is tranquil and covered with vegetation typical to swampland-it's interesting if you can see the differences in the nature of the two lakes where gray mullet and eel swim around the reeds.

Once we reach Otranto we take time to explore. Otranto was the main port on the southern Adriatic under Byzantine rule, but today the ferry service for Corfu is the only surviving activity connected with the sea. On land, Otranto is a fairytale; medieval, whitewashed town featuring an impressive Aragonese castle and a beautiful Byzantine Cathedral with an impressive floor covered in colorful mosaic. The picture perfect waterfront & great outdoors market makes for a timely rest before we take on our 2 hill climbs into a region of unmatched coastal beauty.

Lodgings: 2 nights in a 4-star Patria Palace in medieval center of Lecce & one night at a 4-star hotel on sea with coastal views

Our ride starts off with a steep climb and begins what in my opinion is the finest coastal scenery anywhere on the Adriatic. This jagged coastline of jutting white rocks is lined with vineyards, pine and olive groves along sheer limestone cliffs studded with colorful marine caves and prehistoric habitats. We examine several of the grotto, all worth a prolonged stop.

We soon pass through Castro, whose Greek roots and medieval past are evident by the Cathedral and well-preserved castle that stands at the entrance to the town. Then all too soon we round the heel of Italy—a highlight in itself. Even though the port is rich in natural beauty and has a cultural history dating back to the Messapian era, as well as a medieval and Roman past, I find the lighthouse more of a realization of what we’re doing. The first time I rode this route, 25 years ago, a strange awareness of how far I was from the civilized world overcame me. How ironic, as much of history’s civilization had graced this same port in the quest of delivering civilization to the world.

The coast on the other side of the heel starts to flatten out and the dramatic high rocky coast gives way to a low-lying pine forest. With the wind at our back and a flat terrain in front of us we pass by a charming fishing village then skirt the long beaches leading to quaint ports. Upon our first glimpse of Gallipoli in the distance, you know you are approaching a very special place. We soon cross over its 17th century bridge to the little island known as “the city”. A medieval breakwater encloses the entire island within a network of twisting turning streets barricading the historic center and concurrent, oddly shaped white buildings.

Watching the fishermen work against this backdrop makes one realize why it’s often called one of the most scenic waterfronts in Italy; and we surely understand the Greeks' aptly simple sobriquet: "Kalé polis", Greek for "beautiful town". Visit to the ancient underground olive oil presses that provided lamp oil for many centuries and were considered not only the leaders in the industry, but established pricing standard for the world.

Lodgings: seaside albergo on island town of Gallipoli .