This packed 16-day adventure combines the culturally rich region of Sicily with one of Italy's less-heralded gems: Puglia. First, you're off to the heel of Italy's boot, home to ancient and unique cities like Matera and Alberobello. Then you'll jet to Sicily, where you'll hop in a rental car and drive across the island, stopping at ancient Greek and Roman ruins along the way.

Highlights

  • Roadtrip through Sicily, from Palermo to Catania
  • Visit 9,000-year-old cave dwellings in Matera
  • Tour charming Alberobello and its traditional trulli structures
  • Visit Greek and Roman ruins at Agrigento and Syracuse

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 Lecce to Bari - Afternoon Food Tour Bari
Day 7 Bari Free Day Bari
Day 8 Flight from Bari to Palermo - Pick up Rental Car Palermo
Day 9 Guided Tour of Palermo - Visit Monreale Palermo
Day 10 Drive from Palermo to Marsala - Wine Tasting Marsala
Day 11 Drive from Marsala to Agrigento - Tour Valley of the Temples Agrigento
Day 12 Drive from Agrigento to Syracuse - Visit Ragusa Ibla & Scicli Syracuse
Day 13 Explore Syracuse - Day Trip to Noto Syracuse
Day 14 Syracuse to Taormina - City Tour Taormina
Day 15 Guided Mount Etna Hike - Wine Tasting Taormina
Day 16 Drive from Taormina to Catania - Departure  

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: Lecce to Bari - Afternoon Food Tour

Touring Bari's historic old town
Touring Bari's historic old town

After a relaxed breakfast hit the road for the 2-hour trip north to the city of Bari, on the Adriatic Coast. The city is famous for its port and university, and is southern Italy's second-most important economic center, after Naples. 

Bari's old town, known as Barivecchia, was its center during Roman times and is now a popular meeting place filled with restaurants, bars, and historic, medieval buildings. Notable churches include the 12th-century Basilica of Saint Nicholas, the 13th-century Bari Cathedral, the newer Russian Orthodox Church (a popular pilgrimage site for Russian and Greek Orthodox worshippers), the 11th-century San Giorgio degli Armeni, and the 17th-century Baroque Santa Teresa dei Maschi

The city is also home to the grand 19th-century Petruzzelli Theatre, the 12th-century Castello Svevo (now a museum), the Piccinni and Margherita Theaters (the latter is now a museum), and the Pinacoteca Provinciale di Bari museum of painting and art. 

When the weather is nice, the Orto Botanico di Bari (botanical gardens) is the perfect place for a stroll or an afternoon picnic.

After lunch, meet up with a guide for a walking street food of Bari. You'll go off the beaten path in the city center, as well as the medieval city streets, to discover hole-in-the-wall cafes and family-owned joints. Try local specialties, such as focaccia barese (the local take on an Italian classic) and panzerotti, a sort of fried pizza calzone with a legendary following.

Day 7: Bari Free Day

Bari from the old aqueduct bridge
Bari from the old aqueduct bridge

Your day is free to explore the city. Perhaps spend some time diving into history and art at the city's museums. In the afternoon, you can explore the Grotte di Castellana, a sprawling cave system located in Bari's countryside. This half-day tour includes transportation from Bari, entrance to the caves, and a guided tour of the cave system. Learn about the 90-million-year-old history of the caves, from their origin in the Cretaceous period to the modern-day. Return to Bari in the evening.

Day 8: Flight from Bari to Palermo - Pick up Rental Car

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 pick up your rental car and drive 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 9: 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 10: Drive from Palermo to Marsala - Wine Tasting

Evaporating salt ponds near Marsala
Evaporating salt ponds near Marsala

This morning you'll drive southwest along the western edge of Sicily toward Marsala, taking in the stunning views of the dazzling salt pans that edge the sea. Dotted with historic windmills, saltwater lagoons, and mounds of harvested salt, the salt flats create a chessboard pattern evoking an otherworldly landscape. Spend a little time walking the tourist paths that run the length of the basins filled with slowly-evaporating seawater before reaching Marsala and your hotel. After checking in, set out to explore your surroundings. 

A city well known for its fortified wine of the same name, its baroque old town center is pedestrian-friendly and offers pretty views of baroque buildings, peppered with elegant piazzas. Find your way to a local cantina to meet the winemakers as well as to sample a varietal or two (or three!) paired with regional specialties.

Day 11: Drive from Marsala to Agrigento - Tour Valley of the Temples

Scala dei Turchi
Scala dei Turchi

In the morning, continue your drive southeast along the coast to Agrigento. En route, stop at the chalk-white limestone cliffs of Scala dei Turchi to stretch your legs and admire views over the sea. Resume your journey until you reach Agrigento, a UNESCO-protected archaeological site. Here you'll meet with a licensed guide to discover the ruins of the ancient city of Akragas in the Valley of the Temples, so named for its well-preserved Greek temples. One such intact gem is the Temple of Concordia, one of several ridge-top temples that once served as beacons for homecoming sailors. 

At the end of the tour, you'll make the 5-minute drive to your hotel in Agrigento, a hilltop city on Sicily's southwestern shore. After checking into your accommodation, set out to explore your surroundings. Stroll through Agrigento's densely-packed historical core, finding your way to Via Atenea, the main thoroughfare lined with shops, restaurants, and bars. Leading off Via Atenea, you'll climb your way upwards through a maze of cobblestoned narrow alleys and side streets past 18th and 19th-century palazzi (noble homes or mansions).

Day 12: Drive from Agrigento to Syracuse - Visit Ragusa Ibla & Scicli

Ragusa Ibla
Ragusa Ibla

Today you'll drive from Agrigento to Syracuse, stopping to explore two incredible UNESCO-listed baroque destinations: Ragusa Ibla and Scicli. 

The road trip begins with a 2.5-hour drive south along the coast to the hilltop town of Ragusa Ibla. You'll meander the narrow lanes of its historic center, stopping to relax in a café or gelateria. If you're up for it, climb the 250 steps to the 18th-century Duomo di San Giorgio, a great example of baroque style. For more exercise, head up the stairs to Ragusa's upper town for breathtaking views. Alternatively, you can take a ride on the trenino (little train) from the Piazza Duomo along the city streets.

From here, continue south 45 minutes to the ancient town of Scicli. You can stroll its pedestrianized Via Penna for nice views of nearby baroque palaces and churches, or visit one of its most beautiful baroque buildings, the Palazzo Beneventano, located on nearby Via Duce d'Aosta. If there's time, take the zig-zagging path up to the 19th-century San Matteo Church. Perched on a cliff, it affords sweeping vistas of the town below. You can also visit an old cave settlement in the Chiafura district

When you're ready, continue up the coast 1.5 hours to your hotel on the island of Ortygia, the historical heart of Syracuse. Sometimes called Città Vecchia (Old City), Ortygia is an easily walkable area full of treasures waiting to be discovered. Perhaps begin with a walk around the island before ducking into the network of narrow and winding alleyways, passing churches and baroque palaces as you go. You can't go wrong here, as everything is a visual treat.

Day 13: Explore Syracuse - Day Trip to Noto

View over Noto and its cathedral
View over Noto and its cathedral

Take the day to immerse yourself in historic Syracuse, a UNESCO World Heritage Site. Renowned for its rich Greek history, culture, architecture, as well as the birthplace of engineer and mathematician Archimedes, Syracuse was long regarded as one of the major powers in the Mediterranean. 

Spend the morning exploring the ancient ruins of the Neapolis Archaeological Park. Or lose yourself in Ortygia's winding streets, visiting tucked-away gems like the 19th-century Palazzo Impellizzeri, the Temple of Apollo in Piazza Pancali, or go underground to the San Giovanni Crypt and Catacombs, which date to the 6th century. Alternatively, for some relaxation, you can sunbathe next to turquoise waters at Arenella Beach, just 20 minutes south of Syracuse.

In the afternoon, you'll drive 45 minutes to Noto and explore this postcard-perfect baroque city. In a couple of hours, you can easily cover the town on foot. Stroll Corso Vittorio Emanuele and walk beneath Porta Reale (Royal Gate), taking in the embellished architecture at every turn, like the Chiesa di Santa Chiara, and end your walk at the spectacular 18th-century limestone Noto Cathedral. Optimize your Noto experience with a rewarding granita (frozen dessert) from the popular Caffè Sicilia.

Day 14: Syracuse to Taormina - City Tour

View of Mt. Etna from the Greek theater
View of Mt. Etna from the Greek theater

After breakfast head out for the 1.5-hour transfer to Taormina, a sophisticated and popular resort town located up the coast from Syracuse, on the Ionian Sea. The town's amazing views and ancient theater, which is often used for operatic and theatrical performances, make it the perfect destination for fans of the arts. 

In the afternoon go for a three-hour guided walking tour of the city. Highlights include the 10th-century Palazzo Corvaja, named after one of the city's most influential families, the restored 17th-century Catholic Santa Caterina Church, and the Vicolo Stretto—the narrowest street in town. 

Skip the line to see the Greek theater, which boasts views of Mt. Etna and Giardini Naxos. From here head to the main square of Piazza IX Aprile to rest and refresh with a glass of Mt. Etna's famous wine at a local enoteca.

Day 15: Guided Mount Etna Hike - Wine Tasting

Mount Etna's colorful landscape
Mount Etna's colorful landscape

Get an early start today and head inland toward Europe's largest active volcano, Mount Etna. You'll start in the Rifugio Sapienza, the southern access point to the volcano for your guided hike to Torre Del Filosofo. Rent any walking equipment you may need and then proceed to ride the cable car up 9,500 feet (2,900 m) to Torre del Filosofo. Take in the breathtaking vistas of solidified lava flows, fumaroles, and views that stretch out to the Mediterranean.

Hop back in your rental car and set out to tour the countryside, stopping at a Sicilian winery to sample the regional reds, whites, and rosés. You'll drive past fruit orchards, vineyards, and lava streams, then stop at various wineries to taste local wines, made from grapes grown on the nutrient-rich volcanic earth. Enjoy Sicilian delicacies of cheeses and salamis for lunch.

Day 16: Drive from Taormina to Catania - Departure

Via Etnea and Mount Etna
Via Etnea and Mount Etna

After breakfast, make the hour drive south to Catania. Sicily's second-largest city next to Palermo, Catania sits at the foot of Mount Etna and deserves a little exploration if there's time before catching your departure flight. Depending on traffic, it typically takes 15 to 20 minutes to travel from Catania's center to the airport. Best to arrive at the airport at least two hours prior to your international departure (and with some extra time to drop off your rental car).

Map

Map of Puglia & Sicily Highlights - 16 Days
Map of Puglia & Sicily Highlights - 16 Days