Highlights
- Explore the whimsical town of Alberobello
- Enjoy wine tastings at family-owned vineyards
- Tour a Bronze Age archaeological site in Egnazia
- Take a dip at Polignano a Mare's dramatic Cala Porto beach
- Visit a 15-century castle in Otranto
Brief Itinerary
| Day | Highlights | Overnight |
|---|---|---|
| Day 1 | Arrive in Matera | Matera |
| Day 2 | Ride to Alberobello | Alberobello |
| Day 3 | Locorotondo and Cisternino Loop Ride | Alberobello |
| Day 4 | Ride to Monopoli | Monopoli |
| Day 5 | Savelletri and Torre Canne Loop Ride | Monopoli |
| Day 6 | Ride to Polignano - Alberobello | Alberobello |
| Day 7 | Ride to Ostuni | Ostuni |
| Day 8 | Transfer to Lecce - Ride to Gallipoli | Gallipoli |
| Day 9 | Ride to Santa Maria di Leuca | Santa Maria di Leuca |
| Day 10 | Ride to Otranto | Otranto |
| Day 11 | Ride to Lecce | Lecce |
| Day 12 | Depart Lecce |
Detailed Itinerary
Day 1: Arrive in Matera
Welcome to Italy! You will land in the nearby Bari International Airport-Karol Wojtyla (BRI) and take an hourlong train or taxi ride to Matera. After you check in at your hotel and drop your bags, you can begin exploring.
This ancient town is known for its sassi cave dwellings, which are some of Europe’s oldest settlements as they originated from a prehistoric troglodyte group. You'll feel transported back in time as you roam through its maze of narrow alleys and stone stairs. Many of the houses you'll see are simple caverns, and streets leading to some sassi can be found on the rooftops of other houses.
After you finish wandering around, you might want to find a place to have a relaxing dinner.
Day 2: Ride to Alberobello
You'll pick up your rental bikes after breakfast and start your 42-mile (68 km) ride to Alberobello. Your route will take you through hidden back roads bordered by stone walls, and as you cycle through the countryside, you will pass masserie (fortified farmsteads), grain fields, and olive groves.
As you arrive in Alberobello, you'll see more than 1,000 whitewashed stone houses with conical roofs known as Trulli. Alberobello's abundance of Trulli have made it a UNESCO World Heritage site.
After you check in at your hotel, you'll have the rest of the evening free to spend as you'd like.
Day 3: Locorotondo and Cisternino Loop Ride
On today's ride, you will pass through more rolling hills dotted by endless olive groves and vineyards. You'll begin with a 5-mile (9 km) ride to Locorotondo, a rounded town where sublime white wines are produced. It is widely considered to be one of the most beautiful hamlets in Italy with its lavish churches and a labyrinth of whitewashed alleys.
After you explore Locorontondo, you'll continue your ride further into the countryside, where you'll see more Trulli scattered among the fields. You can stop for a visit in the historic town of Cisternino, where you can have a drink or lunch in its central piazza.
When you're ready to head back, you'll ride about 11 miles (18 km) back to Alberobello.
Day 4: Ride to Monopoli
Today you'll set off for Monopoli, a seaside town that dates back to 500 BC. On your 24-mile (40 km) ride, you'll pass through beautiful ochre-colored fields dotted with olive trees and more Trulli of all sizes.
You'll cycle along a panoramic road that overlooks the Adriatic Sea, with the sea air providing a refreshing breeze as you arrive in the town of Conversano. You'll find that the coastal plains are cultivated with a variety of crops and dotted with elegant farmsteads. You can wander around town and have a bite or a glass of wine before continuing on.
Your final destination is 10 miles (17 km) north, and you'll be treated to more coastal views on your way to Monopoli. When you arrive and check in at your hotel, you can spend the rest of the evening exploring this bustling fishing town and its splendid white-washed houses and narrow alleyways.
Chat with a local specialist who can help organize your trip.
Day 5: Savelletri and Torre Canne Loop Ride
For today's loop ride, you'll cycle about 15 miles (25 km) along the edge of the Adriatic coastline to Savelletri and Torre Canne, with magnificent views of green vegetation lining rocky beaches on your route.
It’s an easy and pleasant ride, and you can choose to make a stop right outside of Savelletri at the archaeological site and museum at Egnazia, where you can marvel at artifacts from the Bronze Age. When you arrive in the resort town of Savelletri, you can spend some time on the beach, play a bit of golf on the nearby golf course, or opt to have lunch.
When you're ready, you will continue on an easy ride through farmlands to Torre Canne. Here, you can see the lighthouse, take a dip in the hot springs, or do some souvenir shopping before returning to Monopoli for the night.
Day 6: Ride to Polignano - Alberobello
On today's ride, you'll have a gradual climb from the Adriatic Sea to the gently undulating Valley of Itria as you make your way through olive groves and fields surrounded by low stone walls.
For the first part of your ride, you'll cycle 5 miles (8 km) to the popular beach destination of Polignano a Mare. You can visit Cala Porto, the beach that made the town famous, have an apertif in the piazza, or visit Fondazione Museo Pino Pascali—Puglia's only contemporary art museum.
As you continue on your 9-mile (15 km) ride back to Alberobello, you can make a stop at Castellana Grotte for a rest and to visit an immense underground cave system that is one of the largest in Europe.
When you arrive back in Alberobello, you'll be able to check in at your hotel and enjoy the evening on your own.
Day 7: Ride to Ostuni
Today's route will take you to Ostuni—a white-washed town perched on top of a hill that overlooks the Adriatic. Along the 21-mile (35 km) route east, you'll have the opportunity to make another visit to Locorotondo. You may want to visit the main cathedral and the church of Madonna della Greca.
As you continue on, you'll come to Cisternino again, where you may want to stop and sample local meat, cheese, wine, and olive oil.
When you reach Ostuni, known as the White City, you will check in at your accommodation and have the rest of the night free to explore.
Day 8: Transfer to Lecce - Ride to Gallipoli
After breakfast, you'll pack up your bag and ride your bike to the Ostuni train station. You'll take a 2-hour train ride to Lecce and bring your bike with you.
When you arrive at the station in Lecce, you'll hop on your bike again for a long day's ride of 24 miles (40 km) down a narrow country lane. You may want to make sure your swimsuit is within reach as you'll be passing some secluded beaches on your route today.
As you ride across the Salento region, you will reach the clear Gulf of Taranto. From there, you'll continue your ride across the flat countryside, and you'll pass large olive trees, pine forests, sand dunes, and ancient lighthouses.
As you approach your destination, the medieval fishing town of Gallipoli, you will find it bustling with life. After you check in at your hotel, you'll have the evening free to explore. You won't want to miss the restored fort known as the Castello di Gallipoli, the town's historic churches, and many cafes and restaurants.
Day 9: Ride to Santa Maria di Leuca
Today's 28-mile (46 km) ride takes you along a coastal road through the southernmost point of Puglia, which divides the Ionian and Adriatic Seas. Before you leave the area surrounding Gallipoli, you can take a swim in the turquoise waters of Torre Del Pizzo beach.
From the beach, you'll continue south to your final destination of Santa Maria di Leuca—a magnificent village with even more stunning beaches and colorful mansions. Once you check in at your hotel, you can explore the village, take a boat to one of the grottos, hike to the top of the Cascata Monumentale, or see the Faro di Leuca lighthouse.
Day 10: Ride to Otranto
On today's 35-mile (57 km) ride north to Otranto, you'll get to take in plenty of fresh air and revel in the sea breeze as you follow a high coastal road that winds along the cliffs.
Have you camera on hand as you'll be passing some incredible views, and stop consider stopping for a glimpse of the spectacular cave known as the Grotta Zinzulusa.
When you arrive in Otranto, a Greek-come-Roman port town, you'll have time to check in at your hotel and drop your baggage before heading out to explore. If you'd like to see intricate 12th-century mosaic floors, consider a visit to the Otranto Cathedral, but if frescoes are more appealing, try the smaller Chiesa di San Pietro. There's much more to see in the city's historic center, including an impressive castle known as the Castello Aragonese Otranto.
Day 11: Ride to Lecce
You'll see another side of Puglia today on your 28-mile (46 km) ride back to Lecce. Along the way, you will have the opportunity to stop and visit the Alimini Lakes that run parallel to the sea.
You'll once again cycle through the countryside of the formerly Greek area of Salento, where traces of former Greek colonies can be found in the dialect, cuisine, and architectural style.
When you arrive in Lecce, you'll be able to check in and relax for the evening, or you can head out to see the baroque buildings and Roman ruins.
Day 12: Depart Lecce
It's time to say goodbye to Italy! Your trip will end after breakfast. After you return your rental bikes, you'll take a train or private transfer to the airport for your flight home.
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