Day One — City tour of Alberobello + 25 km cycling (easy; 1.6 km = 1 mile)

We’ll meet you early morning at the Brindisi Airport and shuttle you to our first city tour in Alberobello. Those who have arrived the day before will be met at your accommodations near Brindisi. Alberobello is a UNESCO World Heritage site, and home of the famous trulli. Unique to Puglia, these circular stone homes are topped with conical roofs of gray limestone, and Alberobello alone has 1,500 of them! After a refreshing lunch, we’ll van a few more kilometers to arrive at our peaceful rural inn. Once you’re settled in to your rooms you’ll have your bicycle adjusted and we're off on our first ride. Bari prides itself on its friendliness toward travellers, in the tradition of their patron saint, Nicola or Nicholas. You’ll appreciate their hospitality as we wind along its back roads and take in the view of the sea before retiring back to the inn. Once back at your inn we'll lounge poolside while sharing the highlights of today’s journey, then partake in a tasting of local olive oils before tucking into a catered dinner.

Day Two — 49 km (easy to moderate)

After a hearty breakfast, you will head out on a loop ride through the towns of Cisternino and Ostuni. After the initial uphill (better to get it over with early in the day!), you’ll meet astonishing views of the surrounding countryside and Adriatic as you cycle along the scenic ridge road to Ostuni. Known as The White City, Ostuni is built on the remains of a prehistoric town destroyed during the final throes of the Second Punic War. Its labyrinthine alleyways and cobblestone streets are ideal for exploring on foot or bike. A stop here is not complete without a visit to the Spanish-influenced, 15th-century cathedral, built under the auspices of the Sforzas, an aristocratic Milanese Renaissance family. Then it’s back to our inn to prepare for another prodigious dinner.

Day Three — 61 km (easy to moderate)

After a van shuttle, you’ll begin your travels through the Salento Peninsula. Today’s breathtaking scenery is characteristically Mediterranean, and not surprisingly, there’s a distinctly Greek atmosphere. Just some of the gems you’ll spot on today’s smooth ride: white sand beaches, the Alimini Lake Oasis, dozens of small, ancestral olive groves and vineyards. You’ll have lunch at a funky seaside trattoria before continuing onward to Otranto, a thriving port town and jewel of the Adriatic. Experience the elegant ambience and breezy night life of Otranto’s well-preserved historic center. Take your pick from one of the many trattorias for dinner and explore the town at your own pace. Don’t miss the Byzantine frescoes and the Castello Aragonese.

Day Four — 65 km (easy to moderate)

Awe-inspiring coastal vistas, hidden grottos, undulating cliffs — just a small part of what our ride has in store for us today. You’ll cycle along the spectacular high coastal road down to the southernmost point of Puglia, Santa Maria de Leuca — home of the famous lighthouse — where you’ll see the Strait of Otranto. This marks the point where the Adriatic and Ionian Seas meet. En route, you’ll pass Grotta Zinzulusa, a fantastic seaside cavern lined with stalactites and stalagmites, and if the tide is right, you’ll be able to tour it. You’ll savour your lunch among the cliffs with stunning views over the Adriatic, then cycle onwards just past Santa Maria Leuca, your home for the evening.

Day Five — 30-40 km (easy to moderate)

Today you leave the Adriatic behind and explore Puglia’s Ionian coast. You’ll encounter flat countryside and a lush panorama as you journey along the western tip of Italy’s heel. Perhaps we’ll stop for a swim with the Naiads in the sparkling sea; if we do, keep your eyes peeled for fossils. With luck, the winds will be in our favour and you’ll end your day with an afternoon ride along Gallipoli Bay.

Day Six — Van shuttle from Santa Teresa to Lecce (plus city tour)

The end point of the Appian Way is the refined city of Lecce — the Florence of the South — where cyclists outnumber cars and Vespas. According to local legend, Lecce was founded during the Trojan War, and it’s now the region’s economic and agricultural center, dealing in olive oils, wines and ceramics. As for its own natural resources, they export Lecce stone, a malleable limestone perfect for sculpture and carving, as well as formidable opera singers and footballers. A guided tour of this small city with its particular brand of Baroque architecture, barocco leccese, will wrap up another amazing day. But not before enjoying our final farewell dinner together in one of our favourite restaurants of the area.

Day Seven — Farewell

After our last breakfast together the tour will end with a transfer to the Brindisi Airport, sad that our adventure is ending but glad to have made new friends.

Details subject to change.