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We love Italy — its scents, flavors, scenery, and people. The landscapes stir the soul, with sweeping vistas of vineyard-cloaked hills, stately cypress trees, and gnarled olive groves grounded in red earth.
The Puglia region, located in the heel of Italy’s "boot," is known for the unique whitewashed architecture in its seaside towns, lack of tourists, and farmland that cascades into coastlines. That alone makes it a wonderful Italy vacation destination, but what truly sets it apart is its spirit. Puglia is a place where the union of art, food, and nature has been celebrated for thousands of years. It is a region that has endured numerous wars and invasions and has been inhabited by dozens of civilizations, all of which have left their mark on the land and culture. On this unique small group guided tour, we venture to this western "gateway to the East" to explore a lesser-known side of Italy the crowds have yet to find.
Boundless Journeys specializes in all-inclusive small group tours around the world. Discover your next adventure abroad among our European guided tours.
Bari and Otranto
Welcome to Puglia! Our adventure begins with a guided tour of Bari's historic center, the capital of the Apulia region. After enjoying lunch at a local restaurant in Bari, we set off on a scenic drive south along the Mediterranean coast. Our destination is Otranto, situated at the easternmost point of Italy on the Adriatic Sea.
Upon arrival, we check in to our hotel and have a brief orientation meeting with our guide. We conclude the day with a delightful dinner together, raising a toast to the exciting adventures that lie ahead!
Corte di NettunoOtranto, Italy
Once a farmhouse, Corte di Nettuno now offers modern rooms and two rooftop terraces overlooking the harbor, all just a 10-minute walk from Otranto's center. Throughout the hotel, you will find museum-quality nautical artifacts, as well as a restaurant, bar, and internal courtyard.
Otranto and the Adriatic Sea
Today begins with a guided exploration of Otranto. Rich in history, Otranto is situated at the easternmost point of Italy on the Adriatic Sea. Historically, it was a key port during the expansion of global trade, though this also made it vulnerable to attacks by foreign seafarers.
As we stroll through the medieval streets, we hear tales of conquest and visit the Otranto CathedralToday begins with a guided exploration of Otranto. Rich in history, Otranto is situated at the easternmost point of Italy on the Adriatic Sea. Historically, it was a key port during the expansion of global trade, though this also made it vulnerable to attacks by foreign seafarers.
As we stroll through the medieval streets, we hear tales of conquest and visit the Otranto Cathedral - renowned for its impressive 12th-century "Tree of Life" floor mosaic. Next, we head to the coast for a leisurely walk along the picturesque coves for which the area is famous, and if the weather is warm, you might even take a dip in the Adriatic Sea. The evening is yours to relax and explore at your own pace.
Lecce and Alberobello
After breakfast, we transfer to Lecce. Along the way, we stop for a short visit to the Basilica of Santa Caterina. Whatever the motive for the basilica, it is one of Puglia's rare examples of Gothic architecture. The facade is rather plain, but inside is completely covered in colorful frescoes by Francesco d'Arezzo.
Upon our arrival in Lecce, we head to an open-air market to pick up local ingredients for our cooking class. Puglia's cuisine is deeply rooted in the region's agricultural tradition and self-sufficiency. Many of its dishes originate from "cucina povera" (peasant cooking), using natural, genuine ingredients such as vegetables, legumes, seafood, olive oil, homemade pasta, and bread. We reap the benefits of our efforts and enjoy lunch made from the abundant feast we create.
This afternoon we meet a specialist guide for a walking tour of Lecce. Known for its stunning Baroque architecture, Lecce also has deep roots in Ancient Greece, a long history of papier-mache craft, and the vibrant atmosphere of a university town. As we stroll through piazzas, we admire intricate stonework, and learn about the history and culture of this "Florence of the South."
From here, we drive north for approximately 1.5 hours to the beautiful Itria Valley and Alberobello, a UNESCO World Heritage Site, renowned for its "trulli" houses. These stone dwellings with conical roofs are a unique architectural style found only in this valley. Some trulli have been converted into accommodations, and we stay in a typical trullo for the next three nights.
Trulli HolidayAlberobello, Italy
This unique accommodation offers guests an opportunity to spend the night in an authentic trulli house, a traditional style of architecture in the Itria Valley. Rooms are comfortable and tastefully decorated to accentuate the rustic-chic interior.
Ostuni
Our destination this morning is Ostuni, often called la Citta Bianca, or "the White City," due to its bright, whitewashed walls. Originally painted with lime to brighten the dark medieval alleys, the white walls also help keep the interior temperatures of buildings cool. In later centuries, this practice continued during epidemics to help curb the spread of disease.
Our first visit is to a typical "masseria", a farmhouse set on a large plot of land traditionally used for agriculture. These farmhouses, often owned by wealthy barons, feature an architectural style that blends rustic country charm with the elegance demanded by the noblemen who built them. We tour the ancient underground olive oil mill and enjoy a tasting of local olive oil, followed by a delicious lunch.
Later today, we explore the winding streets of Ostuni. The uniform white color of the buildings catches the colorful light of dawn and dusk, creating a charming labyrinth of narrow passages to get lost in. From the highest point in town, we take in sweeping views of the surrounding landscape and the Adriatic coast.
At day's end, we make our way back to Alberobello. The evening is yours to relax, explore, and dine at your leisure.
Itria Valley and Locorotondo
This morning we walk from Alberobello to Locorotondo, a beautiful and ancient town, crossing the Itria Valley. The route takes us along narrow tracks and through areas with ancient olive trees, vineyards, and trulli. At the end of the hike, we visit a family-owned winery to learn about local viticulture and wine production. Of course, we have the chance to taste a selection of their wines.
We also have time to explore the charming town of Locorotondo before returning to Alberobello. This evening, our immersion in Pugliese gastronomy and culture continues with dinner at a local home.
Egnazia and Polignano a Mare
Today we transfer to the Archaeological Park of Egnazia, situated among farms and olive groves on the edge of the Adriatic. Here, we discover extraordinary artifacts and ruins from this once active commercial center of the ancient world.
Later, on our way to Matera, we stop to visit the charming village of Polignano a Mare, perched on limestone cliffs overlooking the Adriatic Sea. Due to the soft nature of the limestone, several naturally formed sea caves were inhabited by prehistoric people. The village center is a lovely network of alleyways winding among typical white houses and small courtyards, leading to terraces with stunning views of the sea.
After lunch in this seaside town, we drive inland for about an hour to Matera, a UNESCO World Heritage town in the Basilicata region. Set on the edge of a ravine, Matera is claimed to be the oldest city in Italy and has been continuously inhabited since the Paleolithic Era.
After checking in, we enjoy our first glimpse of the enchanting alleys and unique architecture of this troglodyte town. We might enjoy an aperitivo before wandering back through the maze to rejoin the group for dinner.
Alvino RelaisMatera, Italy
Alvino Relais, at Matera's historic north gate, epitomises luxury and elegance with lush gardens, sun-soaked terraces and a delightful swimming pool. The hotel is housed in a meticulously restored historic mill, preserving its timeless charm with local materials and craftsmanship.
Matera
Our day begins with a hike to the Murgia plateau, facing Matera, where we admire the 8th-century rock churches, once inhabited by hermits and adorned with Byzantine frescoes.
Upon our return to Matera, we enjoy a guided walk through the Sassi district. Formerly one of Italy's poorest areas, the district once saw entire families living alongside their livestock in cave dwellings without running water or power. This situation led to frequent outbreaks of malaria and other diseases, and the area was often referred to as "Italy's shame". The city began to modernize in the mid-20th century when the government relocated inhabitants from the grottoes to newer buildings. Today, the revitalized Sassi district presents a well-preserved living history, with some former cave dwellings now serving as restaurants and inns.
We have the late afternoon free to explore and enjoy Matera independently before gathering for a farewell dinner to celebrate our journey!
Departure
Today we say arrivederci to Puglia! A group transfer to Bari Airport will be provided after breakfast.
Please note that this is a typical itinerary, and actual activities may vary due to weather conditions, local events, and to allow serendipity to play a hand in your experience. Accommodations are as outlined in the itinerary, although we reserve the right to change these or the order visited should the need arise.
8 Days
May 1-8, 2025
Sep 25-Oct 2, 2025
Take over a date for your group! See "Make It Private" on Dates & Prices tab.
From $5,295 Per Person
First one reserved:$395
Additional:$895
See single supplement policy below.
MAKE IT PRIVATE
Call for pricing: 1-800-941-8010 or email info@boundlessjourneys.com
SINGLE SUPPLEMENT: Accommodations are based on double occupancy. A single supplement is paid by participants who specifically request single accommodations, subject to availability.
Single Supplement for Scheduled Group Departures. If you reserve at least 120 days prior to departure, you may be eligible for a reduced or free single supplement. This is generally limited to the first one or two solo travelers to reserve, and the reduction is outlined in the pricing for each trip. Free or reduced single supplements are not combinable with other offers or promotions.
If you are traveling alone and wish to share accommodations, we will try to match you with a roommate of the same gender. If you reserve at least 120 days ahead and request a roommate but one is not available, you will receive a $500 reduction from the standard single supplement (unless otherwise noted in the detailed itinerary for your specific trip).
Single Supplement for Custom Tours. Custom Tour prices are generally based on two or more participants; therefore, single supplements for “solo” Custom Tours will vary and are available upon request.
Boundless Journeys' trips are designed for energetic and flexible individuals who like to be active and have a spirit of adventure and a positive attitude. Italy: Discovering Puglia is rated 2, easy, on a scale of 1-5 (with 5 being the most strenuous). It features walks of varying lengths and easy-to-moderate difficulty that average 3-6 hours per day. Walks on this tour will be on varying terrain, including cobblestone streets in and around villages and some dirt roads and trails. Walks are broken up by rest, cultural activities, and meals. Please refer to the detailed itinerary for descriptions of the activities on each day of the trip.
At the Dillman Luxury Stay in Bari, Italy at 9 a.m.
The tour ends after breakfast on Day 8. A group transfer is provided to the Bari airport.
Most Convenient AirportBari Airport in Bari, Italy (Airport code BRI)
Arrival RecommendationWe recommend arriving in Italy at least one day before your tour begins. This will give you time to rest after your travels and recover from any effects of jet lag. It may be most convenient to spend a pre-trip night at the Dillman Luxury Stay in Bari, as this is our meeting place on Day 1.
Meeting Time and PlaceIn the lobby of the Dillman Luxury Stay in Bari at 9 a.m.
Departure Time and PlaceThere will be a group transfer to Bari Airport (about 1 hour driving time) after breakfast on Day 8. We recommend scheduling your departing flight no earlier than noon.
The weather in late spring and early fall is usually very pleasant, with daytime temperatures ranging from the low 60s to the upper 80s, dropping to the 50s and 60s at night. While these months are not in Italy's "rainy season," there can be cool breezes or showers at any time.
Alberobello
High: 72 Low: 55
High: 78 Low: 62
Lecce
High: 68 Low: 55
High: 75 Low: 64
The shoulder seasons of late spring and early fall take advantage of warm weather while avoiding the crowds of (often Italian!) tourists who flock to Puglia in July and August. Daytime temperatures during May and September are usually warm enough to swim, but still cool enough for comfortable walking. Springtime sees colorful wildflowers in bloom, cascading over stone garden walls. In the fall, vineyards burst with purple grapes as the harvest begins.
Italy is famous for its cuisine, and with good reason. Located in the heel of Italy's "boot," Puglia is a traditional agricultural region, known for homestyle, country-inspired cuisine. Local wheat, tomatoes, artichokes, beans, fennel, peppers, onions, beef, and lamb are commonly found in many dishes. Puglians pride themselves on their pasta, orecchiette, shaped like little shells and usually served with meat and vegetable-based sauces. Puglian pasta is traditionally made only from durum wheat flour, water, and salt, because eggs were historically considered a luxury. In addition, fresh burrata, an abundance of seafood on the coast, and desserts made from regional almonds, honey, and sweetened ricotta cheese ensure a complete experience of local flavors.One dinner (on Day 3) is not included in your trip cost as we believe that venturing out on your own is an important part of discovering a new culture. Vegetarians can be accommodated.
With a Boundless Journeys guide, your experience is that of friend and local adventurer. We believe strongly in working with local guides, experts in the areas to which we travel, and they hold the keys to unlocking the hidden delights of your chosen destination. Although you will never know they are at work—the mark of a truly great leader—our guides make magical things happen and add a dimension to your trip that you could not experience on your own. Over the years we have forged bonds with some of the best guides in the world, and we typically work with a small team of guides in each region. You will be informed of the guide for your trip one month prior to your departure.
We love Italy — its scents, flavors, scenery, and people. The landscapes stir the soul, with sweeping vistas of vineyard-cloaked hills, stately cypress trees, and gnarled olive groves grounded in red earth. The Puglia region, located in the heel of Italy’s...
Easy to moderate walking, 3-5 hours per day on varying terrain, including cobblestone streets, city streets, and some dirt roads and trails.
This trip can be your own adventure by taking over one of our scheduled dates, or we can request a fresh one.
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