Italy: Bike Tour of Puglia

2019 Dates: Oct. 6-13, Oct. 13-20 (sold out), 2019
2020 Dates: Oct. 4-11, Oct. 11-18, 2020

This tour explores Puglia, a spectacular region in the south of Italy. Here the Ionian and Adriatic seas give us warm weather, blue-green crystal clear waters, and endless white sand beaches, while inland our easy cycling takes us past vast groves of gnarled olive trees, green pastures with sheep and goats, yellow fields of wheat, and Italy’s largest and most beautiful vineyards. There is a wonderful variety of towns and villages with their grand medieval houses, ancient cathedrals and fortresses, and wonderful small parks and narrow streets where around every corner you might find bits of Renaissance sculpture, tumbling flowers, and splashing fountains. And then there is the food! Pugliese food is delightfully simple, local, and often enjoyed with superb local wines. Enjoy freshly caught fish, the trademark orecchiette pasta, and local lamb, the centerpiece of many meals. And in Puglia the vegetables and cheeses have an almost cult status, so that even the simplest brushetta with arugula, homemade mozzarella and fresh tomatoes makes for a perfect Italian midday meal.

Our tour is a leisurely highlight reel of all these things that make Puglia so special. Each day combines perfect cycling (and daily additional options) with wonderful feasts, the very best accommodations, and visits to such places as Matera with its haunting sassi district; Alberobello with its comical trulli; Ostuni the iconic “white city”; the island “old town “ in Gallipoli; serene and beautiful Santa Maria di Leuca; historic Otranto overlooking the Adriatic; and Baroque and beautiful Lecce, the “Florence of the south.” You will not want this tour to ever end!

Puglia Italy Bike Tour Itinerary

DAY ONE  | Arrival Day  |  Hotel Sant’Angelo
Discovery Bicycle Tours will meet you at Bari Airport and transfer you from there to Matera. After checking in to our hotel, we are treated to a guided tour of the town, a designated UNESCO Heritage site. Matera is most famous for its two “sassi districts.” The sassi are ancient cave dwellings which were carved into the local limestone hills as much as 9,000 years ago. These are now mostly fashionable modern dwellings and hotels, but in the past, were over-crowded cramped quarters (often consisting of a single cave “room”) that were home to both livestock and their owners. Small lanes, alleys and stairways wind through the districts, and we include a visit to the Casa Grotta di Vico Solitaro, an excellent exhibit that replicates what these ancient cave dwellings were like. From here we might visit the handsome 13th-century Romanesque Matera Cathedral (1268-1270), and take a lighthearted stroll to the town center, Piazza Vittorio Veneto where small shops and trattorias line the square.

DAY TWO  |  Distance: 42 miles  |  Terrain: Easier to Intermediate | Trulli e Puglia

Today’s ride takes us along the rich farming area of the Murgia Plateau. We may include a visit to the magnificent castle at Gioia del Colle before arriving at Alberobello, our destination for the next two nights. Alberobello is another UNESCO World Heritage site that is world-renowned for its wonderful concentration of the curious houses known as “trulli.” Trulli are magical looking white-washed cone-shaped houses whose cobbled roofs are usually decorated with fanciful painted symbols. They look like fairy tale houses and you fully expect a small elf or hobbit to pop out a front door at any minute. Some of these trulli date back to the Middle Ages, and most are still lived in by the townspeople, or are used for stores, restaurants, and lodging (in fact our hotel here is a series of connected trulli). Alberobello is a lively place, and while roaming the ancient narrow cobbled streets (the main activity here), you will delight in the unusual stores and small restaurants, a number of interesting museums, and perhaps a visit to Chiesa Sant ‘Antonio located at the top of the Rione Monti.

DAY THREE  |  Distance: 24 miles  |  Terrain: Easier to Intermediate | Trulli e Puglia

Today we enjoy a loop ride through farmland dotted with rural “trulli” to the famous Grotte di Castellana. Here we include, for those inclined, an optional tour of this complex of expansive caves with their incredible subterranean network of rooms filled with wildly colorful stalactite and stalagmite formations. Our ride back takes us back into Alberobello by way of ancient farm roads that criss-cross the valleys. Tonight we are treated to a demonstration by a local chef in the art of making a gourmet pasta meal featuring orecchiette — the local specialty — and fresh mozzarella cheese.

DAY FOUR  |  Distance: 26 miles  |  Terrain: Easier to Intermediate | La Sommita
This day begins with a ride out of the Trulli region. We stop in Cisternino and enjoy the labyrinth of narrow streets in the historic “old town.” Our lunch-time destination includes a superb olive oil tasting at D’Amico Olive Oil Press before riding to Ostuni. Ostuni is known as the “white city,” a reference to the dazzling effect of the sun as it beams down on the town’s beautiful whitewashed houses. Certainly one of the most stunning cities in southern Italy, this chic and extremely popular town offers us a maze of sunlit streets, winding staircases and narrow alleyways — all emanating out from the handsome town center. Here we find ancient ramparts and a huge Gothic cathedral (built in 1495) that rises above the remains of a Norman castle.

DAY FIVE  |  Distance: 31 miles  |  Terrain: Easier | Hotel L’Approdo
This morning we transfer by van to Gallipoli, a fishing village located on the Ionian Sea. Gallipolli’s old town is built on an island set in the Gulf of Taranto and is linked to the mainland by a 16th century bridge. Formerly one of the richest towns in Puglia, Gallipoli retains an elegant air and the white alleyways of the old town are a joy to explore. Today’s ride is spectacular! The Ionian seashore is especially beautiful and our route takes us past medieval watchtowers strung out along impossibly white beaches and a sea that comes in beautiful shades of violet and turquoise. Moving slightly inland we pass through tiny villages, olive groves and vineyards as we make our way to the very bottom of the Italian “heel” to “finibus terram” or land’s end at elegant Santa Maria di Leuca. This exceedingly popular destination has a lovely promenade, trendy nightclubs and beautiful villas, and for centuries its port has been the landing stage for big fishing boats and yachts. High on the bluff and protecting the harbor is the town’s iconic lighthouse from which you can walk down to the port by navigating a magnificent 284-step staircase.

DAY SIX  |  Distance: 25 miles  |  Terrain: Easier to Intermediate  |  Hotel Papaleo
Our cycling today takes us along the more remote southern coast of the Adriatic Sea. This area features dramatic views of rocky cliffs, grottoes, and beautiful scenery along unspoiled coastline. It is dotted with a rich array of architecture-from medieval to Byzantine to Baroque-all reflecting the relentless waves of invaders that made a habit of trying to conquer this peninsula. Gentle roads next lead us north to the historic seaside town of Otranto. Important as a Greek and Roman port, Otranto has a colorful and mixed past and its historic town center is strategically set high on a hill overlooking the port. From here its Romanesque cathedral and the 15th Century Aragones Castle afford superb views along a series of picture-perfect sandy beaches. One of Otranto’s famed attractions is a twelfth-century mosaic located on the floor of the town’s main cathedral.The mosaic is astonishingly detailed and borrows its images from pagan times; ancient Greek and Hindu mythology; the Old and New Testaments; and medieval history. In the evening we can enjoy the nightly “passeggiata” of the townspeople as they engage in the Italian pastime of an evening stroll. We also include a wonderful wine and cheese tasting featuring some of the best local products.

DAY SEVEN  |  Distance: 32 miles  |  Terrain: Easier to Intermediate  |  Hotel Risorgimento
Today we ride inland along quiet country lanes and farmland, and through beautiful olive groves, to Lecce, “the Florence of the South.” Here we will find some of the loveliest, most elegant and fanciful Baroque architecture in all of Italy. For centuries local craftsmen have taken advantage of the unique softness of the local yellow limestone so as to carve exuberant demons, animals, flowers, fruits into every corner of even the most humble of buildings. We will enjoy a guided tour through the old town with its small squares and delightfully twisted streets. We will visit the dramatic remains of a Roman amphitheater and the Piazza del Duomo, Lecce’s unique town center. Here we view the jaw-dropping extravagantly ornate facade of the 16th-century Basilica of Santa Croce, a massive cathedral sandwiched between a five-story bell tower and the ancient bishop’s palace.

DAY EIGHT  |  Departure Day

After breakfast today we will help you arrange for your transport back to the airport in Brindisi or in Bari (taxi fare not included in tour price) … or help you arrange a few extra nights in Puglia. Ciao!

Puglia, Italy


Make your reservation with confidence. Your 2020 tour is completely 100% refundable up to 90 days of the tour date


October 6-13, 2019:  $3495  
Reserve with $300 deposit


October 13-20, 2019:  $3495  (Sorry! Sold out.)
Reserve with $300 deposit


October 4-11, 2020:  $3495  
Reserve with $500 deposit


October 11-18, 2020:  $3495  
Reserve with $500 deposit

Final payment for your 2020 tour is due 90 days prior to your tour (personal check, Visa, MasterCard, American Express or Discover)

Single Supplement Fee: $490

Cancellations: If you cancel your tour reservation, your cancellation fee will be determined as follows:

  • If you cancel 90 or more days prior to the start of your tour, there is no cancellation fee.
  • If you cancel between 60 and 89 days prior to the start of your tour, you will forfeit 50% of all tour payments.
  • If you cancel between 0 and 59 days prior to the start of your tour, all tour payments will be forfeited.


logo-puglia-italy-sant-angeloA luxury resort in the enchanting location of the Sassi of Matera. Only here in Matera, you can eat and sleep in the stylish rooms carved into the rock of Civita Matera, you can walk through the tunnels and courtyards furrowed by man.

logo-puglia-italy-trulliWhen you visit this land, it changes you to your very core. There is a sweet serenity in the simplicity of the hearts in these streets of stone. Life’s “complicated” details melt away…your daily worries- obsolete…and you lose yourself to the wonders of this peoples’ love that starts in their soil, and to the history that actually still lives to this day.

The Relais “La Sommità”, one of the few 5 star hotels in Puglia, is a historic 16th century residence, which represents a jewel in the crown of this old town of Ostuni, a renowned tourist resort in Puglia and noted as the “White city”.

logo-puglia-italy-laDesigned in Typical Mediterranean style, situated in a panoramic position, overlooking the Marina of Santa Maria di Leuca . Its comfortable rooms, its spacious lounges, the beautiful swimming pool surrounded by greenery, the sea-view terrace and a typical and prestigious restaurant make it an “approdo” magical and authentic.

In the historic center of Otranto, Hotel Palazzo Papaleo is the charming hotel that you’ve dreamed of for your vacation in Salento, a historic residence near the sea, carefully renovated with splendid rooms with every comfort.

Every detail at the Risorgimento Resort makes your stay memorable and exclusive –the timeless charm of the historic architecture, the pleasant welcome, the sophisticated taste of Puglia cuisine and the intimate way of wellness living.

What’s Included

A cooking demonstration in Alberobello, all entry fees, all transfers during the tour, 7 nights lodging, 7 breakfasts, 5 dinners (you are on your own one night in Ostuni and we have a late afternoon wine and cheese tasting in Otranto), bicycle and helmet, free transfer from Bari International Airport, and to Brindisi Airport. Airfare is not included.


We are happy to provide you with a bike to use at no charge. Our bikes come equipped with a front handlebar bag, rear carrier, water bottle, mirror and flat pedals. Pedal cages and soft gel seat covers are available on request. We are also happy to put your own clipless pedals (pedals that attach to your biking shoes) and seat on your bike if you wish. Specific details and styles of bikes available in each location are indicated under each photograph below. The make of bikes provided varies by location.

Virtual Tour of Puglia, Italy