Over 10 days you'll explore Puglia and Sicily, two of the most historic and culturally unique regions of Italy. You'll begin this southern adventure with a tour of colorful villages like Alberobello and ancient cave dwellings in Matera. Then you'll arrive on the island of Sicily,  where you'll embark on a street food tour of Palermo, visit Greek ruins at Segesta, and laze on the beaches of Cefalú. 

Highlights

  • See storybook trulli homes in Alberobello
  • Visit 9,000-year-old cave dwellings in Matera
  • Tour the historic plazas and Baroque fountains of Palermo
  • Roam ancient Greek temples at Segesta

Brief Itinerary

Day Highlights Overnight
Day 1 Arrival in Puglia - Transfer to Alberobello Alberobello
Day 2 Alberobello Tour - Rione Monti & Aia Piccola Alberobello
Day 3 Day Trip to Matera Alberobello
Day 4 Alberobello to Lecce - Afternoon Cooking Class Lecce
Day 5 Lecce City Tour Lecce
Day 6 Flight from Bari to Palermo Palermo
Day 7 Guided Tour of Palermo - Visit Monreale Palermo
Day 8 Day Trip to Cefalù Palermo
Day 9 Day Trip to Segesta & Erice Palermo
Day 10 Depart Palermo  

Detailed Itinerary

Day 1: Arrival in Puglia - Transfer to Alberobello

Traditional trulli homes in Alberobello
Traditional trulli homes in Alberobello

Welcome to Italy's southern Puglia region—the heel of the boot! From the airport at the capital of Bari, you'll transfer about an hour southeast to Puglia's fertile green countryside and the town of Alberobello. Upon arrival in the town center, you'll check into your hotel.

Alberobello is a unique and charming place, which you'll discover on a self-guided tour. This UNESCO World Heritage Site is most famous for its trulli, circular 14th-century limestone buildings with conical roofs. These whitewashed storybook structures are used for everything from shops and restaurants to tourist lodgings and private homes. Other notable sites in town include the 17th-century Basilica, the trullo Church of St. Anthony, and the heritage museum Trullo Sovrano. 

Alberobello also hosts many festivals during the summer, from an international folk festival to jazz, theater, and children's events. There are even religious festivals with music and fireworks, most of which are free. In the summer, the city's culture of passeggiata—long, leisurely evening strolls—continues well past midnight as pedestrians enjoy the warm summer nights.

Day 2: Alberobello Tour - Rione Monti & Aia Piccola

Church of Alberobello
Church of Alberobello

Today you'll have a guided tour of Alberobello. The UNESCO World Heritage trulli district in Alberobello is one of Puglia's most popular attractions, and the rest of the town is also lovely. Begin the tour on the road from Aia to the Trulli district, which stretches over seven hills. 

The center of the city looks like most Italian small towns, with a few trulli located here and there. Head to the Rione Monti district to see many of these pointy white buildings clustered together. The neighborhood is situated on several narrow lanes on a hillside and is full of little gift shops selling souvenirs and Trulli-themed gifts. You'll have time to wander the picture-perfect streets to find everything from colorful terracotta whistles (a favorite local gift) to trulli-shaped knickknacks. 

Exploring the hidden nooks of this neighborhood is a tour highlight, as many of the buildings contain tiny bars and the panoramic views from the terraces are stunning. Once you've explored to your heart's content, head up the Via Monte Michele to the Chiesa di Sant'Antonio, Alberobello's 20th-century Trullo church. 

Continue to Alberobello's second trulli district—the quiet residential Aia Piccola, which is less frequented by tourists. The rest of the city is mostly composed of typical Italian buildings, with the occasional trulli popping up here and there. Conclude your tour with a visit to 18th-century Trullo Sovrano, the largest trullo home. This two-story building houses an excellent history museum and is outfitted with period fittings illustrating Italian life in the 1700s.

Day 3: Day Trip to Matera

Santa Maria de Idris rock church
Santa Maria de Idris rock church

In the morning, you'll transfer an hour west to the ancient hilltop city of Matera, where you'll enjoy a three-hour walking tour. The town is famous for the Sassi di Matera, well-preserved cave homes cut into the soft rock. These unique dwellings are considered to be some of Italy's first human settlements and are a designated UNESCO World Heritage Site. 

The Sassi are located on both sides of the valley. The Sasso Caveoso on the south side are the most historically fascinating, while the Sasso Barisano are commercially developed and house offices and residences. The city of Matera also has many beautiful winding stairways, as well as incredible churches carved into the side of the volcanic rock.

You'll tour the city as well as the unique cave dwellings and rock churches as you learn about the city's history from your guide. See the cathedral of Sasso Barisano, as well as some of the filming locations for Mel Gibson's film The Passion of the Christ

Day 4: Alberobello to Lecce - Afternoon Cooking Class

Basilica Di Santa Croce
Basilica Di Santa Croce

After breakfast, hit the road for the 1.5-hour trip to Lecce, a historic city on the coast of the Ionian Sea. It's the central city of the Salentine Peninsula and is over 2,000 years old. Thanks to its Baroque architectural monuments commonly found in the city, Lecce is nicknamed the "Florence of the Baroque" or "Rome of the South." 

Lecce has a distinctly Greek culture, stemming back to its foundation by the Messapii, a lapygian tribe said to have been from Crete. The city's main attractions include Piazza San Oronzo, the 17th-century Duomo (designed by G. Zimbalo), Porta Napoli (the original gate to the old town), the Obelisk (erected in the 19th century to honor  Ferdinand I of the Two Sicilies), and the beautiful Paisiello Theatre.

The Baroque 17th-century Basilica Di Santa Croce (Holy Cross Church) and 15th-century Torre del Parco are popular sites in the city center, while the Orto Botanico di Lecce (University of Lecce botanical garden) is a peaceful nature sanctuary featuring hundreds of fruit trees and other plants. 

In the afternoon get a taste of authentic local cuisine during a 3-hour cooking class at an expansive Lecce estate. You'll join the estate's owners, both professional sommeliers, in creating a full dinner of Pugliese specialties. Sit down to enjoy your meal, paired with a selection of fine wine. 

Day 5: Lecce City Tour

Santa Cesarea, Villa Sticchi
Santa Cesarea, Villa Sticchi
Explore Lecce's city center on today's half-day walking tour. Your guide will lead you through the historic buildings and explain the traditions behind the local crafts—papier-mâché, wrought iron, ceramics, and inlaid olive wood. 
 
Spend the afternoon enjoying nature in Lecce's public gardens and beaches. If you've got some extra time, head out of town to La Cutura Giardino Botanico, a wonderful botanic garden located in Giugianello, a half-hour drive south of Lecce. 

Puglia's beaches are renowned for their rock formations and turquoise sea. Gallipoli Beach is one of the area's most popular, and Santa Cesarea Terme is a great place to explore small rocky pools. Spiaggia di Alimini is a 35-minute drive to the southeast of the city and is considered the area's finest beach for its white sand dunes and diverse ecology.

Day 6: Flight from Bari to Palermo

View over Palmero at sunset
View over Palmero at sunset

It's time to say goodbye to Puglia! At the appropriate hour, private transport will take you to the Bari airport for your flight to Palermo, which lasts a little over an hour. Sicily's regional capital boasts beautiful Mediterranean weather and a long and storied history with Roman, Byzantine, Arab, and Norman influences. You'll see this mix of cultures reflected in Palermo's architecture, music, and cuisine. 

Upon arrival at the airport, you'll transfer 45 minutes to your hotel in the heart of the city to settle in. The rest of the day is yours to spend as you like.

You can discover Palermo right away on a self-guided walking tour. The best place to begin is Palermo's historic center. Its medieval streets are easy to navigate by foot, and there are many attractions and restaurants within walking distance. To get your bearings, take a passeggiata (stroll) along the narrow Via Maqueda, a pedestrianized thoroughfare that connects the north of the city to the south. A good place to start is the Fontana Pretoria, a Baroque fountain in the Piazza Pretoria.

Day 7: Guided Tour of Palermo - Visit Monreale

View of the cityscape from the Palermo Cathedral rooftop
View of the cityscape from the Palermo Cathedral rooftop

In the morning you will meet your guide for a private half-day tour of the Sicilian capital. Quattro Canti (officially known as Piazza Vigliena), Palazzo Reale, the 12th-century Duomo (the Palermo Cathedral), and Marina Square are some examples of the architectural masterpieces you'll come across. You'll also visit Capo Market, a great spot to pick up some lunch or a typical snack like panelle (chickpea fritters) and cazzilli (pan-fried potato croquettes).

In the afternoon, you might consider driving a short way to the town of Monreale. On the slopes of Monte Caputo, you'll discover what is thought to be the greatest example of Norman architecture in the world, the Cattedrale di Monreale (Monreale Cathedral). This 12th-century UNESCO Heritage Site is made up of ornate cloisters and gold mosaics featuring scenes from the Old and New Testaments. Admire the Norman-Byzantine art and architecture as you tour this national monument.

When you're ready, spend a little time wandering Monreale itself. Consider a stroll through the Belvedere public garden where you can enjoy a beautiful view over the Conca d'Oro below, a fertile valley abounding with citrus trees.

Day 8: Day Trip to Cefalù

The seaside town of Cefalù
The seaside town of Cefalù

Start your morning with a scenic one-hour train ride on the coast to Cefalù, a historic port town. You can start a self-guided tour in the city center at the Lavatoio Medievale, a 16th-century washhouse that utilizes running water from the River Cefalino in its stone basins. Nearby is the Porta Pescara, a gate to Cefalù Beach featuring great views of the coast. Perhaps take a walk to the old harbor and stroll the seaside promenade; the city's Lungomare Beach is also a popular destination. 

You should definitely visit the 17th-century Bastione di Capo Marchiafava, one of many old defensive fortresses located along the coast. The view from the top of the Bastione is a real treat. Right nearby is the Norman-Arabic Duomo Basilica Cattedrale (Cefalù Cathedral) which dates to the 12th century. And if there's time, climb the Rocca, the promontory above the city. A steep staircase winds through city walls before emerging onto a rocky outcrop with stunning views of the city and ocean. 

Stop at a beachside bar for an aperitivo before catching the train back to Palermo. 

Day 9: Day Trip to Segesta & Erice

The 2400 year old Greek temple
The 2400 year old Greek temple

Depart from Palermo in the morning for a full-day excursion to Segesta and Erice. Start in Segesta, an archaeological complex located an hour away from Palermo. 

The first thing you'll notice when you arrive in Segesta is the 2400-year-old Greek temple, which stands alone on its pedestal hill. Nearby you can see the medieval ruins and the ancient Agora, but the next highlight is further up on the hill—the theater, which dates to the 3rd century BCE. Behind the stage, you'll find an incredible panorama of hills and the Tyrrhenian Sea. 

Afterward, transfer to Erice, a medieval city famous for its narrow winding streets, medieval arches, and decorated courtyards. Enter the old city by the Porta Trapani, then walk to the historic city center to reach the 14th-century Duomo, which houses marble sculptures, and the next-door bell tower. Climb the 110 steps to the top for a view of the city. 

From here, follow the old city walls for a panoramic viewpoint, then explore the city's Spanish neighborhood, as well as the Church of San Giovanni Battista, Castello di Venere, and the 19th-century Torretta Pepoli. The Castello is a 12th-century Norman defensive fortress which houses ruins of a Roman spa and a temple. 

Make your way back to the city gate, pausing at the Piazza Umberto I to see the ornate palazzi and Museo Antonio Cordici, which displays traditional crafts and trades. 

Day 10: Depart Palermo

The Porta Felice, Palermo
The Porta Felice, Palermo

In the morning, if you have time, head to the Foro Italico. This large public garden along Palermo's seafront makes an excellent spot to soak in the sunshine before heading to the airport. You may also like to explore Villa Giulia, a sprawling 18th-century complex of botanical gardens and sculptures. Then perhaps stroll along the Foro Italico to Porta Felice, a 16th/17th-century monumental gateway to La Cala (Old Port).

Depending on traffic, it usually takes 45 minutes to an hour to travel from the center of Palermo to the airport. Best to arrive at least two hours prior to your international departure while allowing extra time to drop off your rental car. Have a great trip!

Map

Map of Puglia & Sicily Highlights - 10 Days
Map of Puglia & Sicily Highlights - 10 Days