Sicily Highlights Self-Drive Tour with Aeolian Islands - 10 Days

Day 1: Arrive in Catania - Private Transfer to Milazzo

Welcome to Sicily! Upon your arrival at the Catania airport, you'll be picked up and taken by private transport to Milazzo, a charming coastal city that gives easy access to the Aeolian islands.

Take time in the evening to settle into your hotel and explore the historic medieval center of Milazzo. Say hello to the 18th-century  Shrine of St. Francesco di Paola as you enter the historic quarter, explore the 16th-century Milazzo Castle and its imposing fortressed walls, and visit the 16th century Palace of the Viceroy with ornately decorated baroque balconies later added in the 18th century. 

Day 2: Explore the Aeolian Islands: From Milazzo to Lipari

After breakfast, make your way to the harbor to embark on a hydrofoil to reach the beautiful Aeolian archipelago—seven UNESCO-protected volcanic jewels in the cobalt Tyrrhenian Sea that each offer stunning and diverse landscapes. The first island you'll visit is Lipari, the largest and most populated of the Aeolian Islands.  After checking into your accommodation, take the rest of the day to explore the town-of-the-same-name, Lipari, at your leisure. Find your way to the fortified Castello, a citadel at the heart of Lipari, and a good place to start.

In the evening, head to the modern part of Lipari and to the Marina Piccola, a lovely little harbor. At night the area is bustling with people enjoying an aperitivo and children playing in the square.

Day 3: Transfer to the Island of Stromboli

Today, head to the island of Stromboli, home to one of three active volcanoes in Italy and once referred to as the "Lighthouse of the Mediterranean" by the Romans. After a two-hour boat ride, you'll arrive at the island's northeastern settlement and see for yourself the impressive volcano from the shore. Billowing with smoke, this natural wonder dominates the island's landscape. Take a moment to check in to your hotel, and go for a stroll in the part of Stromboli known as San Vincenzo.

Day 4: Stromboli: Afternoon Guided Volcano Hike

In the morning, you're free to explore on your own. Relax on the beaches of this Italian island, or visit the volcanological center for a complete look at the famous volcano. Perhaps even take a boat tour to reach secluded Ginostra, one of the smallest existing Italian villages that can only be accessed by boat. 

In the afternoon, you'll gear up and join your certified volcanic guide for an exhilarating excursion to the top of the impressive volcano, reaching Stromboli's peak at sunset—the best time to witness its spectacular pyrotechnic display of red and orange lava. The trek is for the confidently fit and as it ends in the evening, the descent takes place in the dark with flashlights.

Hiking time: 5 hours over 3,302 feet (924 m)

Day 5: Return to Milazzo - Drive to Palermo and Visit Cefalù

This morning you'll return by boat to the port town of Milazzo. From here, you'll pick up your rental car and begin your discovery of the Sicilian mainland, driving to Palermo.

Along the way, you'll stop in Cefalù, a famous seaside resort town with a rich history, for a day of self-guided exploration. Head to the city center to see the top sights and start at the Lavatoio Medievale, a 16th-century washhouse. Nearby is the Porta Pescara, a small gate that opens onto a view of the Cefalù beach and the coastline to Palermo. Walk down to the old harbor and stroll along the seaside promenade, stopping to check out the popular Lungomare beach. Before you leave, visit the Bastione di Capo Marchiafava for sweeping vistas and the 12th-century Duomo Basilica Cattedrale (Cefalù Cathedral).

After a full day, you'll continue 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. 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.

Driving time (Milazzo to Cefalù): 1.5 - 2 hours
Driving time (Cefalù to Palermo): 1 hour

Day 6: Guided Tour of Palermo

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).

In the afternoon, take advantage of the nice weather to explore more of the city. Head to the beautiful 12th-century Cappella Palatina inside the Palazzo dei Normanni, a symbol of Palermo. The interior is particularly splendid, with intricate mosaics of saints decorating the walls and ceiling. Later, enjoy nature on a relaxed stroll along the seaside to the Palermo harbor, or with a visit to the I Giardini Inglese and Villa Garibaldi gardens. For a religious and cultural experience, follow in the footsteps of pilgrims up to the Sanctuary of Santa Rosalia, a mountainside chapel dedicated to Palermo's patron saint.

Day 7: Drive from Palermo to Agrigento - Visit Monreale

Get an early start today and make the short drive 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). 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.

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 loaded with citrus trees.

From here, continue on your way to 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).

Driving time: (Palermo to Monreale): 30 minutes
Driving time (Monreale to Agrigento): 2.5 hours

Day 8: Drive from Agrigento to Syracuse - Guided Tour of Valley of the Temples

After breakfast, you'll visit Agrigento's 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. 

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 along Passeggio Aretusa to the shrouded-in-Greek-myth Fonte Aretusa (a natural spring surrounded by stonewalls, planted papyrus, and quacking white ducks). Tuck into the tightly woven network of narrow and winding alleys and lanes, discovering churches and baroque palaces in various states of repair. 

Day 9: 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 10: Drive from Syracuse to Catania - Depart

After breakfast, make the hour drive north 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 Church of Sant'Agata al Carcere in Piazza Santo Carcere or visit 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).