Cycling Puglia

Alberobello – Ostuni
Biking
After breakfast, we'll continue riding the area’s rolling hills, passing through whitewashed villages and along quiet roads lined before reaching the beachside, and the beautiful seaside town of Ostuni. Somewhat resembling Greek island villages, Ostuni is known as the “white city,” for it gleaming jumble of white houses, churches, and charming piazzas spread over a hilltop facing the sea. After being destroyed by Hannibal during the Punic Wars in the 1st and 2nd Centuries BC, Ostuni was then rebuilt by the Greeks. Ostuni takes its name from the Greek expression “Astu neon,” meaning "new town." Ostuni later flourished during the Italian Renaissance under Duchess Isabella of Bari. After lunch, the final part of the afternoon will be spent visiting an area olive mill set amid ancient olive orchards. There, we’ll have the opportunity to do an olive oil tasting. Tonight, we’ll settle into a cozy countryside hotel not too far out of Ostuni where we’ll also enjoy dinner together. The remains of the evening are at your leisure to explore town or relax at the hotel.

Distance: 45 km / 28 mi
Ascent: +329 m (1,080 ft)
Descent: -708 m (2,323 ft) 
Meals: Breakfast, Dinner

Accommodation: Countryside Hotel

Ostuni - Gallipoli
Train Transfer & Sightseeing
After breakfast, we will have the day off riding and will set out on a train journey to Gallipoli. The train heads south from Ostuni, leaving behind the murgia plateau and the olive groves. On the way we’ll transfer in the bustling town of Lecce before catching our local train to Gallipoli, a beautiful town surrounded by defensive walls built in the 14th century. The town’s labyrinthine, narrow streets lead to a gorgeous seaside promenade, and the old town center actually sits on a tiny island connected to the mainland by a 17th century bridge.  After arriving in town this afternoon, you’ll be able to explore the “old” village of Gallipoli right outside your hotel. The evening is at your leisure to explore town, with dinner on your own.

Meals: Breakfast
Accommodation: Hotel

Gallipoli - Leuca
Biking
After feasting on a hearty Italian breakfast, we're back on our bikes today cycling along the Gulf of Taranto, the largest gulf in the Ionian Sea. On our way to Leuca, we'll first pedal to the southeastern tip of Italy and look out on the Ionian Sea and, if it is a clear day, we’ll be able to see Albania and Greece from there. This area is home to a wide variety of beautiful beaches including the “Salento Maldives,” an area resembling the tropical islands after which the area was nicknamed.  As you cycle, you might just fall in love with this rugged yet inviting coastline, its beautiful blue water contrasting the white limestone cliffs and sandy beaches. After arriving into Leuca early evening and settling in at the hotel, you’ll be able to explore the town at your leisure, with dinner is on your own tonight.

Distance: 55 km / 34 mi
Ascent: +316 m (1,037 ft)
Descent: -319 m (1,047 ft)
Meals: Breakfast, Lunch
Accommodation: Hotel

Leuca - Otranto
Biking
After breakfast this morning, we'll pedal north alongside the Adriatic Sea to Otranto, one of Puglia’s historic fortified fishing villages, located at the very tip of Italy’s boot heel. If time and weather permits, we recommend a dip in the sea. Our route continues on the coast with chances to stop and enjoy the views of the rocky (sometimes sandy) beaches. We’ll also pass a number of defensive “towers” built in the 16th century to defend the coast from seafaring marauders. A town once bloodied and bruised by an infamous Turkish massacre in 1480, Otranto is now best known for its magnificent cathedral. For those interested in history, inside you’ll discover the bones of 813 martyrs on display in a glass case behind the altar. After arriving into Otranto early evening and settling in at the hotel, we’ll have dinner together in town. Afterwards, you’ll be able to explore the town at your leisure.

Distance: 52 km / 32 mi
Ascent: +619 m (2,030 ft)
Descent: -618 m (2,028 ft)
Meals: Breakfast, Lunch, Dinner

Accommodation: Hotel

Otranto - Lecce
Biking
Our final ride is a calm and scenic pedal into the charming city of Lecce, often nicknamed “Florence of the South” for its beautiful and historical baroque buildings.  A section of today's ride is through a car-free nature preserve.  We'll arrive into Lecce early afternoon and have some time to freely wander through the village. Later, we’ll enjoy a farewell dinner together in town with the remains of your evening at leisure to take in one last night of the region’s culture and atmosphere. 

Distance: 55 km / 34 mi
Ascent: +312 m (1,024 ft)
Descent: -264 m (866 ft)
Meals: Breakfast, Lunch, Dinner

Accommodation: Hotel

Lecce – Bari (or Brindisi)
Departure

The trip ends this morning in Lecce. Transfers can be arranged to the Bari or Brindisi airports or the train station, at an additional cost. If you prefer to fly out of Rome or Naples, which are bigger airports with more international departures, you can easily plan to take the train to either of these cities from Lecce. You might even want to continue to explore Italy from there. Either way, we know you’ll carry fond memories with you of your days riding through the south with us!

Meals: Breakfast

NOTE about Ascent/Descent numbers: 

The ascent/descent numbers are usually generated using Ride with GPS. The numbers are TOTAL ascent/descent for the day and these numbers do not suggest altitude. There are usually multiple small ascents and descents added up throughout the day to reach this total ascent/descent for the day. (While our numbers are generally consistent with Ride with GPS, depending on the mapping technology used, numbers may vary).