Sicily Highlights Self-Drive Tour with Aeolian Islands - 16 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 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, for a glass of sweet Malvasia wine. At night the area is bustling with people enjoying an aperitivo and children playing in the square.

Day 3: Day trip to Vulcano Island

With its black sand beaches and relaxing hot springs, the island of Vulcano isn't to be missed. Take a boat to the nearby island and discover all its natural beauty. Enjoy a hike up to the crater rim of the volcano the island is named for, and see the steam coming from the fumaroles (vents of volcanic gas). From here, you'll also have an incredible view of the entire Aeolian archipelago. If there's time, consider heading to the island's famed mud baths for a novel way to unwind after your trek, before heading back to Lipari for the evening. 

Walking time: 3 hours
Walking distance: 5 miles (8 km)

Day 4: 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 5: 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 6: Return to Milazzo - Drive to Palermo and Visit Cefalù

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

Along the way, 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 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 7: 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 8: 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 9: 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. Here you'll 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 10: 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 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. 

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

Day 11: 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 as you like. 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 12: Day Trip from Syracuse to Ragusa Ibla, Modica, and Scicli

Today is a free day to spend as you choose and you might like to make the most of your proximity to the incredible UNESCO-listed cities of Ragusa Ibla, Modica, and Scicli.

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 is Modica a little way south (30 minutes). Built on the sides of a canyon, the city is known for its traditional chocolate, following 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 as well as find a selection of restaurants amid elegant 18th and 19th-century buildings. 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 13: 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 be sure to visit the Chiesa Madonna della Rocca for a bird’s eye view of the city.

Find your way to the main square of Piazza IX Aprile to rest and refresh with a glass of Mount Etna's famous wine at a local enoteca before retiring to your accommodation for the night.

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

Day 14: 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 15: Drive from Taormina to Catania

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 its share of exploration. Having suffered from a massive eruption in 1669, followed by an earthquake in 1693, Catania was largely rebuilt during the Baroque era and has some stunning buildings to show for it, like the impressive baroque Church of Sant'Agata al Carcere in Piazza Santo Carcere. Note the whimsical Fontana dell’ Elefante, a fountain made from lava rock in the piazza's center.

Driving time: 1 hour

Day 16: Depart Catania

If there's time before dropping off your car rental and catching your departure flight, you might like to enjoy one last granita (crushed ice dessert) and complete a little souvenir or gift shopping at the traditional Fera o'Luni market. Held daily in Piazza Carlo Alberto, the market sells everything from street food and produce to local crafts and antiques.

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).