Meet at the Brindisi airport for a transfer to the start of our Puglia tour near the enchanting seaport of Otranto. After a bike fitting and safety talk, we’ll set off on our bikes through a sea of olive trees. You’ll soon realize why Puglia is the biggest olive-producing region in Italy as you cycle through this stunning landscape. Stop at a local cantina for a wine tasting and lunch before looping back along the coast into Otranto. Tonight we’ll experience the famous Southern Italian hospitality during our first Pugliese dinner.

Accomplished: 19 miles / 30 km, elevation gain: 731 feet / 223 meters

Shorter Option: 12 miles / 19 km, elevation gain: 377 feet / 115 meters

Today we’ll ride one of the most stunning coastal roads in Europe with breathtaking views of cliffs, bays, and the endless sea. Pass through fishing villages like Porto Badisco and Santa Cesarea Terme. Our destination is Leuca, a lighthouse and sanctuary that has drawn pilgrims for centuries. Here the land ends as we reach the heel of the Italian boot. This afternoon, take a swim, challenge yourself with some extra miles and stop for a seafood lunch at our friend’s restaurant overlooking a small fishing port. This evening, explore historic Otranto; your guides are happy to recommend their favorite local restaurants for dinner.

Accomplished: 30 miles / 49 km, elevation gain: 1,637 feet / 499 meters

Longer Option: 60 miles / 96 km, elevation gain: 3,411 feet / 1,040 meters

This morning we’ll transfer north to the stunning Itria Valley. Our first destination is a small farm that produces mozzarella: before we begin biking, we’ll taste some life-changing cheese and other farm-fresh products. Today’s ride takes us to the picturesque village of Locorotondo, known for its maze of white-washed streets and considered one of the most beautiful villages in Italy. Stop for lunch at our friend Davide’s local trattoria, then ride through the rolling hills and stunning green farmland of the Valle d’Itria to our trulli hotel, created from the restoration of an abandoned rural hamlet or borgo. Spend the afternoon relaxing by the pool before we regroup for dinner.

Accomplished: 26 miles / 42 km, elevation gain: 1,430 feet / 436 meters

Shorter Option: 17 miles / 27 km, elevation gain: 991 feet / 302 meters

Ride across the Itria Valley through pastures and vineyards, past Puglia’s trulli houses on our way to the UNESCO World Heritage Site of Alberobello. Here, our friend Mimmo will show us around his town before inviting us to a home-cooked lunch in his family’s trullo. After lunch, transfer or cycle with spectacular views of the coast to our final hotel, a countryside masseria, or fortified farmhouse, that has been transformed into a five-star luxury resort. Tonight, we dine alongside locals at an unforgettable traditional restaurant.

Accomplished: 16 miles / 26 km, elevation gain: 1,430 feet / 436 meters

Longer Option: 37 miles / 60 km, elevation gain: 1,797 feet / 548 meters

Cycle along the coast through the quaint fishing village of Savelletri, past the Roman ruins of Egnazia, and down tiny roads that wind through endless, centuries-old olive groves. We’ll visit the beautiful masseria of our friends Chiara and Filippo where we’ll taste their olive oil and prepare our own lunch at a cooking class. After lunch opt to go directly back to the hotel, or bike up the ridge for a stunning view of this colorful canvas: the bright blue Adriatic set against the rich brown and vibrant olive green hues. This evening we’ll celebrate this amazing region with a farewell dinner at our hotel.

Accomplished: 26 miles / 42 km, elevation gain: 991 feet / 302 meters

Shorter Option: 13 miles / 21 km, elevation gain: 315 feet / 96 meters

After breakfast on the terrace, enjoy a stroll on the grounds of the masseria or take a morning dip in the pool, play some tennis, or visit the beach. Your guides will then transfer you back to Brindisi as you head on to your next destination.