Spend two weeks delving into Sicily's historic and cultural highlights on this complete itinerary. Discover remote island settlements on Stromboli, meander and climb the narrow laneways and staircases in Modica, Ragusa Ibla, and Scicli,  and dine on fresh seafood in sophisticated Taormina. You'll begin and end in lively Catania and spend four nights on the Aeolian Islands before picking up your rental car and touring the Italian island from Palermo to Taormina, with Cefalù, Agrigento, and Syracuse in between.


  • Walk along Cape Milazzo for striking views of the Tyrrhenian Sea
  • Trek up to the peak of Stromboli for a spectacular display of volcanic fireworks
  • Stroll through Monreale Cathedral's ornate cloisters and manicured gardens
  • Marvel at the well-preserved mosaics in Villa Romana del Casale
  • Hike Mount Etna, Europe's largest active volcano

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Catania; Private Transfer to Milazzo Milazzo
Day 2 Explore the Aeolian Islands: From Milazzo to Lipari Lipari
Day 3 Day trip to Vulcano Island Lipari
Day 4 Transfer to the Island of Stromboli Stromboli
Day 5 Stromboli: Afternoon Guided Volcano Hike Stromboli
Day 6 Return to Milazzo; Drive to Palermo and Visit Cefalù Palermo
Day 7 Guided Tour of Palermo Palermo
Day 8 Drive from Palermo to Agrigento; Visit Monreale Agrigento
Day 9 Guided Tour of Valley of the Temples Agrigento
Day 10 Drive from Agrigento to Syracuse; Guided Tour of Villa Romana del Casale Syracuse
Day 11 Guided Tour of Syracuse Syracuse
Day 12 Day Trip from Syracuse to Ragusa Ibla, Modica, and Scicli Syracuse
Day 13 Drive from Syracuse to Taormina; Guided Mount Etna Hike Taormina
Day 14 Drive from Taormina to Catania; Depart  

Detailed Itinerary

Day 1: Arrive in Catania - Private Transfer to Milazzo

Italy - Sicily - Milazzo Castle (Castello di Milazzo)
Explore the 16th-century Milazzo Castle and its imposing fortressed walls

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

Italy - Sicily - Lipari - Archaeological site showcasing ancient ruins
Visit historic ruins in 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: Day trip to Vulcano Island

Italy - Sicly - Vulcano - People relax in a mud pool on Vulcano Island
Soak in the mineral-rich mud of Vulcano's famed baths

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

Italy - Sicily - Stromboli - Black sand beach of Stromboli
Find your way to Stromboli's black sand beach 

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

The isolated settlement of Ginostra
Ride a boat to the isolated settlement of Ginostra

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)

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

Italy - Sicily - Cefalù - Typical street in Cefalù
Wander Cefalù and its quaint cobblestoned streets

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 is at the Fontana Pretoria (fountain) in Piazza Pretoria. From there, see art at the Stanze al Genio tile museum and Palazzo Abatellis, or spend a few hours in the Galleria Regionale.

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

Day 7: Guided Tour of Palermo

Italy - Sicily - Palermo - Palermo's Baroque Piazza Vigliena (Quattro Canti)
Visit Palermo's Baroque Piazza Vigliena (Quattro Canti)

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

Italy - Sicily - Monreale - Close up of the intricate stone work of the Norman-Byzantine Monreale Cathedral
Stroll through Monreale Cathedral's cloisters and gardens

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.

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

Italy - Sicily - Agrigento - Temple of Concordia
Visit the Temple of Concordia, an imposing intact-gem

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

Italy - Sicily - Syracuse - Castello Maniace at the tip of Syracuse's Ortygia Island
Visit the 13th-century Castello Maniace at the tip of Syracuse's Ortygia Island

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

Ruins of Ancient Greek Theater in Neapolis Archaeological Park
Discover the Ancient Greek Theater in Neapolis Archaeological Park

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 12: Day Trip from Syracuse to Ragusa Ibla, Modica, and Scicli

Italy - Sicily - Modica - Duomo di San Giorgio -
Climb the steps to Modica's Duomo di San Giorgio 

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, 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. 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

Italy - Sicily - Mount Etna in the Autumn
Mount Etna in the Autumn

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 or visit the Chiesa Madonna della Rocca to enjoy 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.

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

Day 14: Drive from Taormina to Catania - Depart

Villa Bellini, Catania, Sicily, Italy
Stroll through the manicured Villa Bellini

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 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).


Map of Sicily Highlights Self-Drive Tour with Aeolian Islands - 14 Days
Map of Sicily Highlights Self-Drive Tour with Aeolian Islands - 14 Days