Our guides meet you in Lecce 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 in Otranto to explore the town before completing the loop back to the hotel. Tonight, head to a small winery to experience the legendary hospitality of Southern Italy during our first Pugliese dinner.

Meals: Lunch / Dinner Destinations: Otranto, Minervino, Uggiano la Chiesa Accomplished: 19 miles / 30 km, elevation gain: 731 feet / 223 meters Shorter Option: 12 miles / 19 km, elevation gain: 377 feet / 115 meters Accommodations: Palazzo Ducale Venturi or Le Capase or Masseria Muzza

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.

Meals: Breakfast / Lunch Destinations: Porto Badisco, Santa Cesarea Terme, Castro, Tricase Porto, Santa María di Leuca Accomplished: 30 miles / 49 km, elevation gain: 1,637 feet / 499 meters Longer Option: 40 miles / 65 km, elevation gain: 2,453 feet / 748 meters Accommodations: Palazzo Ducale Venturi or Le Capase or Masseria Muzza

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 Roberto’s local trattoria, then ride through the lush farmland of the Valle d’Itria to our hotel. The design of the property is anchored by its restored trulli, the conical stone structures unique to Puglia. Spend the afternoon relaxing by the pool before we regroup for dinner.

Meals: Breakfast / Lunch / Dinner Destinations: Pascarosa, Locorotondo, Trito Accomplished: 20 miles / 32 km, elevation gain: 1,168 feet / 356 meters Longer Option: 29 miles / 47 km, elevation gain: 1,853 feet / 565 meters Accommodations: Ottolire Resort or Borgo Canonica

Ride across the Itria Valley through pastures and vineyards until you arrive at the enchanting heart of Cisternino, recognized as one of the most picturesque villages in Italy. Our route will pass more and more 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 five-star luxury resort here on the coastal plain. Tonight, we dine alongside locals at an unforgettable traditional restaurant.

Meals: Breakfast / Lunch / Dinner Destinations: Cisternino, Locorotondo, Alberobello, Savelletri Accomplished: 18 miles / 29 km, elevation gain: 1,220 feet / 372 meters Longer Option: 38 miles / 62 km, elevation gain: 1,653 feet / 504 meters Accommodations: Masseria San Domenico or Borgo Egnazia or Torre Maizza

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.

Meals: Breakfast / Lunch / Dinner Destinations: Savelletri, Torre Canne, ruins of Egnazia, Pezze di Greco Accomplished: 27 miles / 44 km, elevation gain: 1,138 feet / 347 meters Shorter Option: 13 miles / 21 km, elevation gain: 535 feet / 163 meters Accommodations: Masseria San Domenico or Borgo Egnazia or Torre Maizza

After breakfast on the terrace, enjoy a stroll on the grounds of the masseria or take a morning dip in the pool, relax at the spa, or visit the beach. We will then transfer you to the Bari Airport as you head on to your next destination.

Meals: Breakfast