Decadent guided cycling in Puglia

Discover Puglia in style with the locals and the best biking!

  • 8 days / 7 nights
  • Central Puglia
  • Salento
  • Bari - Lecce

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Our passionate team of experts is on hand to design your dream trip to Southern Italy.

Trip Overview

Decadent guided cycling in Puglia
This is a luxurious premier guided cycling trip through the region of Puglia, Italy. This area lies in the heel of the boot, along the sun-drenched Adriatic Sea and is known throughout the world for its exceptional cuisine and produce. Spend a week biking the best routes in the region with our expert guides and start-of-the-art support vehicles. Decadent dinners, cultural visits and extravagant hotels will spice up your cycling adventure. We live and breathe this region and truly believe that this itinerary cannot be matched in terms of content and supreme service.


  • Professionally guided cycling each day
  • Exceptional cycling routes that pass through fishing villages, country lanes, ancient olive groves and vineyards, hidden coves, golden beaches, and the unparalleled Itria Valley 
  • Walking tours of Bari, Alberobello, and Lecce 
  • Several DECADENT dinners at famous local establishments 
  • Salento party with local band

Day 1Cycling: Castellana Grotte-Monopoli loop 58km/37mi with optional visit of Bari

Your adventure begins with a walking tour of beautiful downtown Bari, which may be Italy’s most 

underrated and vibrant urban center. Remember to be wearing your biking gear as we will be riding later on today! We will shuttle you to the striking cliff-top town of Polignano a Mare for your custom bike fit and first ride along the beautiful coastline to the tiny bay of San Vito for an exclusive picnic-style lunch. Next we ride up to Conversano, the city of artists. There, 
you will have time to explore the ancient Aragon-style castle and enjoy your first espressino (Puglia’s signature coffee drink). A leisurely ride downhill will bring us to Borgo Bianco Resort & Spa, your stunning five-star home for the next two nights. You will have time to settle into your sublimely appointed room before indulging in a well-deserved dinner at the hotel’s elegant restaurant. 

Day 2Cycling: Castellana Grotte-Monopoli loop 58km/37mi with optional visit to the caves of Castellana

Today’s ride will take us into the northern reaches of the Itria Valley, filled with ancient olive groves and distinctive trulli houses hidden among nut and cherry trees. We will begin with a slight climb back towards Conversano before turning to Putignano and continuing to Castellana Grotte, where we will offer an optional tour of the amazing caverns. For lunch we descend to the coastal town of Monopoli with its seawalls, castle and picturesque cobbled streets. After a delicious meal in one of the town’s many local eateries there is an easy 10km ride back to Borgo Bianco. Our group will rejoin in the early evening for a guided tasting with a local winemaker or sommelier. Then we will shuttle into Conversano for dinner at Pasha, one of the most fabulous restaurants in all of Puglia. Wow, what a day! 

Day 3Cycling: Polignano-Alberobello-LocorotondoSavelletri 60km/38mi (long option to Martina Franca 80km/50mi)

Our first big moving day features some seriously great riding! We will head inland and then uphill 

through the forests toward the UNESCO World Heritage Site of Alberobello, the postcard capital of 
the region. Here, we will meet local superstar Mimmo, who will guide us in an exploration of the 
region’s history, culture, and artisanal products and set our appetites in motion for a lunch feast. After a tasty meal we will continue toward the Cummerse buildings (rectangular with pitched stone roofs) of Locorotondo, which is also known for its light white wine and beautiful views of the entire Itria Valley. From here, our group will diverge, as the more energetic riders head for the town of Martina Franca on the next hilltop, and the others dive down toward the sea. Either way, your journey will end at the spectacular Masseria Torre Maizza, where you can relax in absolute luxury while your dinner is prepared in their renowned kitchen. 

Day 4Cycling: Savelletri-Cisternino-Ostuni loop 68km/42mi (long option along the sea to Torre Canne 75km/47mi)

This morning begins with a lovely climb into the chic and beautiful hilltop town of Cisternino, where you will enjoy sweeping views of the Itria Valley. You will have time for a coffee or gelato to recharge your batteries before continuing your lovely ride along the ridge to La Città Bianca (the white city) of Ostuni, a stunning hilltop jewel with breathtaking sea views. In Ostuni, you will have many options for a delicious lunch on your own,. The long option today will reward diligent cyclists with a gorgeous, breezy ride along the sea before they make their way back to the hotel. The evening will begin with a refreshing aperitivo followed by a memorable seafood meal at Le Palme Beach, a sophisticated beach club, where the very best of the day’s catch is prepared with grace and aplomb. This elegant evening will offer an amazing finish to your journey through the heart of the Itria Valley.

Day 5Cycling: Squinzano-Acaya-San Foca-Otranto 70km/ 43mi

After a lovely last breakfast at Torre Maizza we will shuttle you to the beautiful Masseria Melcarne, the starting point for an amazing day of cycling through the stark and contrasting beauty of the Salento area, home to Puglia’s best wines! We can stop for a swim at one of the amazing beaches along the route before hopping back on our bikes and continuing our journey. We will also stop in the famous castle city of Acaya for a walk around and a killer local lunch. Our destination is the ancient city of Otranto, a must-see that’s one part beach resort, one part Middle Eastern, many parts Italian, and every part enjoyable! After checking into our hotel, we will bring you into Otranto for a stroll by the sea and dinner on your own (we highly recommend the pizza in Otranto). 

Day 6Cycling: Otranto-Santa Maria di Leuca 50km/31mi

At Southern Visions, we save the best rides for last! Breathtaking sea views, natural hot springs, hills, and pine forests make this one of Italy’s most memorable rides. We will ride down to Santa Maria di Leuca. Here you can stand on the southernmost point of Puglia and gaze out to the inviting sea. On the way down, we will stop for a lovely cave tour and, as always, for coffee. Wine tastings and beach visits are also options today. The serious rider who wants a challenge can cycle back to Otranto and enjoy the feeling of accomplishment that comes with completing a full 100km ride! Those of more relaxed persuasions can take the shuttle back to the hotel. Your day will end with an amazing Pugliese style party featuring a decadent dinner memorable festivities hosted by your guides.

(long option: loop back to Otranto 105km/65mi) 

Day 7Cycling: Otranto to Lecce 37km/23mi

On our last bike ride together we head to the capital of Salento, Lecce, known as the Florence of the South. You will find the terrain is mostly flat, passing among endless olive orchards. So, be sure to stop and smell the olives! Your final hotel destination, La Fiermontina Urban Resort, is 

located in a restored palazzo with its own private garden just steps from some of Lecce’s most 
amazing Baroque masterpieces. You will have some time to explore the city and enjoy lunch on your own. Be sure explore the artisan boutiques and stop for a coffee and the amazing pastry known as Pasticciotto Leccese (filled with yummy custard cream). Alternatively you can indulge in some spa treatments at your hotel. For our final dinner together we’ll experience some of the area’s best “Cucina Salentina” cuisine and we will toast all the adventures we have experienced in this unforgettable discovery of Puglia! 

Day 8Departure

After breakfast, we will guide you to the Lecce train station, shuttle you to the Brindisi airport, 

or help you extend your stay in the area.


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