Sicily Highlights Self-Drive Tour - 11 Days

Day 1: Arrive in Palermo 

Welcome to Palermo! Sicily's regional capital boasts beautiful Mediterranean weather, colorful history with strong ties to its Roman, Byzantine, Arab, and Norman past as evidenced in its architecture, culture, music, and cuisine. Upon arrival at the airport, you'll pick up your rental car and drive the 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.

The historic city center and medieval streets are easy to navigate by foot with many attractions and restaurants within walking distance. To get your bearings, take a stroll or passeggiata along the narrow Via Maqueda, a pedestrianized thoroughfare that connects the north of the city to the south. A good place to start, and for fine examples of baroque architecture and sculpture, is at the Fontana Pretoria (fountain) in Piazza Pretoria. See art at the Stanze al Genio tile museum and Palazzo Abatellis, catch a performance at the Teatro Massimo, Italy's largest opera house, or relax on Mondello Beach and enjoy the azure water.

Day 2: Guided Tour of Palermo - Visit Monreale

In the morning you will meet your guide for a private half-day tour of the Sicilian capital—a smart way to experience the city's vibrant culture and artistic and architectural points of interest. 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 will 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).

After the tour, you'll have the afternoon to yourself where you might like to consider making the short drive to visit 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). The 12th-century UNESCO-listed cathedral is made up of ornate cloisters and bright gold mosaics that feature scenes from the Old and New Testaments. Admire the Norman-Byzantine art and architecture as you tour this national monument.

Day 3: Drive from Palermo to Marsala - Visit Erice

This morning you'll drive west along the Castellammare del Golfo coastline to the medieval town of Erice. Perched on a rocky cliff that offers magnificent views over Trapani, the Aegadi Islands, and San Vito Lo Capo, Erice is 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. Follow the old city walls for a panoramic viewpoint, then explore the city's Spanish neighborhood as well as 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, make your way south 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. Join a walking tour of Marsala and start from the impressive Piazza della Repubblica (also an excellent place for restaurants, cafés, and shopping) to delve into the historical attractions, like Chiesa di San Tommaso, the Palazzo VII Aprile, and the ornate 16th century Chiesa del Purgatory. Dine al fresco from a host of restaurant options, followed by a sweet Marsala dessert wine.

Driving time (Palermo to Erice): 2 hours
Driving time (Erice to Marsala): 1 hour

Day 4: Explore Marsala and 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, venture on 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. 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) and treat yourself to a local delicacy: ricotta-based pecorino ice cream.

Driving time (Marsala to Agrigento): 2 hours

Day 5: Guided Tour of Valley of the Temples

Today you'll have the whole day to explore Agrigento and its popular UNESCO-protected archaeological site in the Valley of the Temples—so named for its well-preserved ancient Greek temples. Less a valley and more a ridge, you'll meet with a licensed guide to walk through the ancient city of Akragas with the option to spend a little time at the popular archaeological museum. Stop to marvel at the temples of Hera (Juno), Concordia (an imposing intact gem), and Herakles as you listen to your expert guide share stories that bring the ruins to life.

After the tour, you'll have the rest of the day to spend as you like.

Day 6: Drive from Agrigento to Syracuse - Guided Tour of Villa Romana del Casale

After breakfast, you'll make the 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. 

When you're ready, continue your drive east to your hotel on the island of Ortygia, the historical heart of the city of Syracuse. Sometimes called Città Vecchia (Old City), Ortygia is chock-full of treasures waiting to be explored and comfortably done so on foot. Begin with a walk around the perimeter of the island before tucking into the tightly woven network of narrow and winding alleys and lanes, passing by churches and baroque palaces in various states of repair. You can't go wrong here, everywhere and everything is a visual treat. 

Driving time (Agrigento to Villa Romana): 1.5 - 2 hours
Driving time (Villa Romana to Syracuse): 1.5 - 2 hours

Day 7: Day Trip from Syracuse to Ragusa Ibla, Modica, and 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 the cities were rebuilt in the Sicilian Baroque style.

Drive west first to Ragusa Ibla and spend a few leisurely hours meandering the narrow laneways as you walk under elaborate balconies, stopping to relax in a café or gelateria. Climb the 250 steps to the 18th-century Duomo di San Giorgio to view the only example of a Catalan-Gothic style portal. And if you're up for the exercise, be sure to climb up the steep stairway to the upper town for breathtaking views over Ibla. Alternatively, there's the option to board the trenino (little train) from Piazza Duomo for a casual ride along the city's main streets.

Next up is Modica a little way south (30 minutes). Built on the sides of a canyon, the city is known for its traditionally made chocolate that follows an ancient Aztec recipe. Wander its labyrinth of bustling streets and steep staircases, starting on Corso Umberto in Modica Bassa (Lower Modica) to get orientated. Explore the narrow alleys off of Corso Umberto as you make your way up to Modica Alta (Upper Modica) and its medieval quarter. Here you might like to head up to Pizzo Belvedere for stunning views over the Modica Valley. 

If there's time, travel south (20 minutes) to the often-overlooked ancient town of Scicli. Follow the elegant pedestrianized Via Penna for pretty views of Baroque palaces and churches. You won't want to miss a visit to possibly one of Sicily's most beautiful baroque buildings, Palazzo Beneventano on nearby Via Duce d'Aosta. And if there's time, take the zig-zagging path to the abandoned San Matteo church perched on an overhanging cliff to enjoy the sweeping vistas of Scicli below or visit the (also abandoned) cave settlement in Scicli's old Chiafura district. 

After a full day, when you're ready, make the return drive back to Syracuse.

Driving time (Syracuse to Ragusa Ibla): 1.5 hours
Driving time (Scicli to Syracuse): 1.5 hours

Day 8: Guided Tour of Syracuse

Dedicate the morning to explore the ancient ruins of the Ionian coast on a guided tour of Syracuse (about three hours). Venture to the Neapolis Archaeological Park for a stroll among the ruins and ancient relics together with your expert guide. Learn about the region's Greek and Roman history as you explore the architecture and then continue the walking tour through Ortygia—Syracuse's beautiful old town, located on a spit of land which extends into the Mediterranean. 

The afternoon is yours to spend at your own pace. Lose yourself in the winding streets, stumbling across tucked-away gems, like the late 19th-century noble residence, Palazzo Impellizzeri, done in the indulgent Rococo style, the Temple of Apollo in Piazza Pancali, or go underground to explore the honeycomb network of the San Giovanni Crypt and Catacombs, which date back to the 6th century. Alternatively, if you're in need of a little relaxation and less sight-seeing, soak in the Sicilian sunshine on the beautiful sand and turquoise water of Arenella Beach, just 20 minutes south of Syracuse.

Day 9: Drive from Syracuse to Taormina - Guided Mount Etna Hike

Get an early start today and head up the coast before cutting 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 reach the Mediterranean.

Upon your return to your car, you'll continue the day's drive to Taormina, a sophisticated and famous resort town located on the Ionian Sea. The town's incredible views and ancient Greek theater, often used for operatic and theatrical performances, make it the perfect destination for fans of the arts. Visit the restored 17th-century Catholic Santa Caterina Church and stroll along the Vicolo Stretto—the narrowest street in town. Discover the 10th-century Palazzo Corvaja, named after one of the city's most influential families and the Chiesa Madonna della Rocca to enjoy a bird’s eye view of the city.

Driving time (Syracuse to Mount Etna): 1.5 - 2 hours
Driving time (Mount Etna to Taormina): 1.5 hours

Day 10: Taormina Cooking Class

Enjoy a leisurely morning, starting the day's activities with a private cooking class. Join your chef as he leads you through a guided market tour. You will visit the fruit and vegetable vendors to find out what’s in season, and the fishmonger to choose the best fresh catch of the day in Taormina’s historic fish market. After the market tour, you'll return to the kitchen for your hands-on cooking class for the preparation of a full Sicilian menu and a typical dessert. Lunch, accompanied by local wines, will follow featuring the foods prepared in class.

The rest of the day is yours to explore Taormina at your own pace.

Day 11: Drive from Taormina to Catania, Depart

After breakfast, make the hourlong transfer south to Catania. The second-largest city next to Palermo, Catania sits at the foot of Mount Etna and deserves a little exploration if there's time before dropping off your car rental and catching your departure flight. Enjoy one last granita (crushed ice dessert) and consider a visit to the impressive baroque Church of Sant'Agata al Carcere in Piazza Santo Carcere or the San Nicoló l’Arena, Sicily's largest church (famous for its unfinished façade).

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).