Puglia & Sicily Highlights - 18 Days

Day 1: Arrival in Puglia - Transfer to 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

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

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

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. 

Day 5: Lecce City Tour

Day 6: Lecce to Bari - Afternoon Food Tour

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 panzerotto, a sort of fried pizza calzone with a legendary following.

Day 7: Bari Free Day

Your day is free to explore the city. Perhaps spend some time diving into history and art at Bari'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

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

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 - Visit Erice

This morning you'll drive two hours west along the coast to the medieval town of Erice. Perched on a cliff that offers magnificent views, Erice is famous for its winding streets, stone archways, and decorated courtyards. Enter by the Porta Trapani, then walk to the historic city center and the 14th-century Duomo. Follow the ancient city walls and visit the Castello di Venere, a 12th-century Norman defensive fortress which houses ruins of a Roman spa and the Temple of Venus.

When you're ready, drive one hour south along the western edge of Sicily toward Marsala, taking in the stunning views of the salt pans that edge the sea. Dotted with historic windmills and saltwater lagoons, these salt flats create a chessboard pattern evoking an otherworldly landscape. Spend a little time walking the pathways that run the length of the dry seawater basins 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. There is more to this charming town besides touring wineries (which is highly recommended). 

Day 11: Explore Marsala & Wine Tasting - Drive to Agrigento

Enjoy a leisurely morning of self-guided exploration with a visit to the Baglio Anselmi Archaeological Museum to learn of Marsala's epic past. Here you'll find impressive artifacts, including a Phoenician boat from the First Punic War among other historic discoveries. And when it's time, you'll find your way to a local cantina to meet the winemakers as well as to sample a varietal or two (or three!) of the fortified Marsala wine paired with regional specialties.

From here, drive two hours to Agrigento, a hilltop city on Sicily's southwestern shore. After checking into your hotel, 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: Guided Tour of Valley of the Temples

You'll have the whole day to explore Agrigento and its popular UNESCO World Heritage archaeological site, the Valley of the Temples, a ridge that's home to well-preserved ancient Greek temples. Here you'll meet with a licensed guide to walk through the ancient city of Akragas with the option to spend time at the popular archaeological museum.

Along the way, you'll stop to marvel at the temples of Hera, Concordia, and Herakles as your expert guide reveals historical insight that brings the ruins to life. You'll also learn how these ridge-top temples once served as beacons for homecoming sailors. After the tour, you'll have the rest of the day to spend as you like.

Day 13: Drive from Agrigento to Syracuse - Tour Villa Romana del Casale

In the morning, you'll make the two-hour drive from Agrigento to discover the elaborate UNESCO-protected Villa Romana del Casale. Here you'll meet with a licensed guide to discover some of the world's best-preserved and varied Roman mosaics as you explore the grounds of this ancient Roman villa. Incredibly luxurious and built on a vast scale, Villa Romana del Casale was probably made for a member of ancient Rome’s elite. 

Afterward, you'll drive two hours east to the island of Ortygia, the historical heart of the city of Syracuse, and check into your hotel. 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 14: Explore Syracuse - Day Trip to Noto

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 15: Day Trip from Syracuse to Ragusa Ibla, Modica, & Scicli

Today is a free day to spend as you choose. You might like to make the most of your proximity to the incredible UNESCO-listed cities of Ragusa Ibla, Modica, and Scicli. In 1693 a devastating earthquake almost erased every town and city in southeastern Sicily after which they were rebuilt in the Sicilian Baroque style.

First, drive 1.5 hours west to the hilltop town of Ragusa Ibla. You can 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.

About 30 minutes south of Ragusa Ibla is Modica. Built on the sides of a canyon, this city is known for its artisanal chocolate. Wander its labyrinthine streets through Modica Bassa (Lower Modica), where you'll find many restaurants amid elegant 18th/19th-century buildings. Follow the alleyways up to medieval Modica Alta (Upper Modica) and Pizzo Belvedere for stunning views over the Modica Valley. Don't miss Duomo of San Giorgio, Modica's main church and a UNESCO landmark.

If there's time, travel south (20 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. 

Day 16: Drive from Syracuse to Taormina - Mount Etna Hike

The day begins early with a two-hour drive up the coast and inland to Europe's largest active volcano, Mount Etna. You'll arrive at Rifugio Sapienza, Etna's southern access point, and prepare for a guided hike. After organizing your equipment, you'll ride a cable car up 9,500 feet (2,900 meters) to Torre del Filosofo, the last accessible lookout point before the summit. Enjoy the breathtaking scenery that includes solidified lava flows, smoke fumaroles, and wide vistas that stretch out to the Mediterranean.

After Etna, you'll continue driving 1.5 hours to Taormina, a sophisticated resort town located on the Ionian Sea. It's famous for gorgeous coastal views and its ancient  Greek theater, the Teatro Antico di Taormina, which is still used for opera and theatre performances. You can also visit the 17th-century Catholic Santa Caterina Church and stroll along the Vicolo Stretto, the narrowest street in town.

Day 17: Cooking Class in Taormina

You're in for a treat, as today you'll partake in a private cooking class. In the morning, you'll meet your chef instructor at a local market for a guided tour. You'll stop at fruit and vegetable vendors to pick up seasonal produce before heading to the fishmonger to choose the freshest catch of the day.

After the market tour, you'll retire to a professional kitchen for your hands-on cooking class. Over a couple of hours, you'll prepare a full Sicilian menu complete with a traditional dessert. Afterward, you'll sit down and enjoy lunch comprised of the foods you prepared in class. Of course, the meal will be paired with local wines. 

Day 18: Drive from Taormina to Catania - Departure

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).