Sicily for Solo Travelers

Board your overnight flight to Palermo today.

Welcome to Italy! Settle into your hotel in Palermo, Italy’s fifth-largest city and the capital of the island of Sicily. Then, gather with your Tour Director and fellow group members at a mixer before enjoying a welcome dinner, served with beer or wine. 

This morning, embark on a guided tour of the bayside city of Palermo. You’ll find yourself on a crescent of land on the Tyrrhenian Sea in an area known as the Conca d’Oro—the golden shell—thanks to its rich soil and abundant citrus orchards.  

• Discover the city’s Baroque architecture as you pass the Quattro Canti piazza in the historic center. Officially known as Piazza Vigliena, the vibrant square features four matching facades, each adorned with ornate sculptures, fountains, and statues representing the four seasons, as well as the patron saints of Palermo.  
• Step inside the Cappella Palatina, a 12th-century chapel that showcases Byzantine, Islamic, and Norman architectural elements. Gaze up at the intricate geometric design of the wooden muqarnas ceiling and spend time poring over the details of the chapel’s elegant mosaics that seem to drape down its walls.  
• Cap your walking tour with a tasting of a sweet local specialty. 

This afternoon, you’ll venture west of Palermo if you add the trip to the ruins of Segesta. There, between rolling hills and olive groves, you’ll find a Doric temple dating back to the 5th century B.C., as well as a Greek theater carved into the hillside. If you prefer to spend your free afternoon on your own, head to Palermo’s Old Town to wander its narrow alleys and lively squares. 

On the way to Syracuse, stop for a guided tour of Piazza Armerina and view the stunning mosaics in the UNESCO-listed Villa Romana del Casale, renowned for its remarkably preserved floor mosaics which offer insight into Roman life and culture in the 4th century. The comune, or town, of Piazza Armerina is itself a charming mix of cobblestone streets, medieval buildings, and Baroque churches—the quintessential Sicilian backdrop.

Later today, continue to Syracuse and sit down for an included dinner, served with beer or wine. Tomorrow, you’ll dive into the history and mythology of this corner of the southeastern coast of Sicily, steeped in Greek, Roman, Byzantine, Arab, and Norman cultures.

No trip to Sicily is complete without a family-style feast. This morning, you’ll start the day at a market, learning about the just-picked produce you’ll use to craft an authentic Sicilian meal during a hands-on cooking class led by a professional chef. Join (flour-covered) hands with your fellow solo travelers in cooking—and promptly devouring—a traditional lunch. You’ll enjoy your creation with beer or wine, of course.

Later, embark on a guided tour of Syracuse, a city known for its rich Greek history.

• Visit the Greek Theater, part of a UNESCO World Heritage Site that dates to the 5th century B.C. From its location, carved into the limestone rock of Temenite Hill, it overlooks the city and sparkling waters of the Ionian Sea. Theater productions and concerts continue there to this day, especially in the summer months.
• Tour the massive Latomia del Paradiso, or Paradise Quarry, and gardens. The quarry played a crucial role in the city’s development and prosperity during ancient times and the limestone extracted from the quarries was used to build the temples and fortifications that made Syracuse into a Mediterranean power.
• Experience the mind-bending echoes of the Ear of Dionysius, a large limestone cave formerly used as a prison. The tyrant Dionysius I used the cave’s unique acoustics to eavesdrop on prisoners.
• Visit the Roman amphitheater, then cross a bridge to the island of Ortigia to see the Temple of Apollo and Cathedral of Syracuse. Still standing as a testament to Syracuse’s Greek history, the Temple of Apollo retains some of its original Doric columns. (Not bad for a 2,600 year old!) Officially known as the  Metropolitan Cathedral of the Most Holy Nativity of Mary, the Cathedral of Syracuse is famous for its Baroque decorations and prominent bell tower. Inside, look for the colorful frescoes, marble sculptures, and embellished altars that decorate the seat of the Archbishop of Syracuse.

Transfer to Taormina, where a local guide will introduce you to this scenic town perched high above the azure waves of the Ionian Sea. Look familiar? This lush Sicilian gem was featured prominently in the series The White Lotus. And understandably so: Its rugged cliffs, ocean-view piazzas, and streets lined with sprays of bougainvillea were, and remain, a magnet for jetsetters.  

• Stroll along the city’s cobblestone paths to see the Cathedral of Taormina, its elegant bell tower rising proudly above the town’s skyline. Continue to visit the medieval walls of the Palazzo Corvaja, the home of the first Sicilian parliament. 
• Visit the town’s 2nd-century Greek theater which, on clear days, offers panoramic vistas of Mount Etna. One of the most iconic—and active—volcanoes in the world, Mount Etna is an ever-present companion in Taormina, inspiring myths, legends, and art in the region.  

On your free day, add an exploration of Sicily’s World War II history to your itinerary with an optional visit to the Museo Storico dello Sbarco. The interactive exhibit features striking photographs and a life-size model of a wartime bunker. When you join the excursion, you’ll also get time in Catania, a city renowned for its Baroque architecture, much of which was rebuilt following a devastating earthquake in 1693.  

If you’re setting off on your own (or with another solo traveler as your companion), we recommend a stroll along Corso Umberto for shopping, people-watching, and a host of trattorias. You can also hike to Castelmola, an adorable hilltop village above Taormina that boasts epic views of the coastline.  

Celebrate your trip at a farewell dinner this evening, served with beer or wine and featuring live music played by local musicians. 

Transfer to the Catania airport for your flight home. Or, if you’d like to squeeze in a few more sips of Aperol spritz or scoops of gelato into your trip, treat yourself to a few days in Rome. You’ll continue your tour of antiquity through romantic piazzas and mysterious catacombs with your fellow solo-travelers-turned-new-friends.