Take in the sights and sounds of Italy's romantic capital, travel along the ruggedly beautiful southern coast, and dive deep into Sicily's ancient culture. You'll do all this and more over 18 unforgettable days, beginning in Rome with tours of the city's emblematic sights before heading to the rocky beaches of the Amalfi Coast and the sunny island of Capri. Then you'll visit the island of Sicily, where you'll experience the best of its culture and cuisine on an adventurous road trip.

Highlights

  • Enjoy four days of private tours, art, and food in Rome
  • Visit the ancient cliffside villages on the Amalfi Coast
  • Take a classic Sicilian road trip from Palermo to Catania
  • Hike Mount Etna with an experienced guide
  • Go wine tasting in both Marsala and Taormina

Brief Itinerary

Day Highlights Overnight
Day 1 Arrival in Rome Rome
Day 2 Vatican & Classic Tour of Rome Rome
Day 3 Private Colosseum & Forum Tour - Cooking Class Rome
Day 4 Galleria Borghese - Free Afternoon in Rome Rome
Day 5 Transfer to Amalfi Coast Amalfi
Day 6 Capri and Anacapri Day Tour Amalfi
Day 7 Free Day on the Amalfi Coast Amalfi
Day 8 Fly From Naples to Palermo - Pick up Rental Car Palermo
Day 9 Guided Tour of Palermo - Visit Monreale Palermo
Day 10 Drive From Palermo to Marsala - Visit Erice Marsala
Day 11 Explore Marsala & Wine Tasting - Drive to Agrigento Agrigento
Day 12 Drive From Agrigento to Syracuse - Guided Tour of Valley of the Temples Syracuse
Day 13 Explore Syracuse - Day Trip to Noto Syracuse
Day 14 Day Trip From Syracuse to Ragusa Ibla, Modica, & Scicli Syracuse
Day 15 Syracuse to Taormina - City Tour Taormina
Day 16 Guided Mount Etna Hike - Wine Tasting Taormina
Day 17 Drive From Taormina to Catania - Fly to Rome Rome
Day 18 Goodbye, Italy  

Detailed Itinerary

Day 1: Arrival in Rome

Colonna di Marco Aurelio in Piazza Colonna
Colonna di Marco Aurelio in Piazza Colonna

Welcome to Rome, City of the Seven Hills! According to legend, Rome was founded by brothers Romulus and Remus in 753 BCE atop Palatine Hill. The long-time center of the powerful Roman Empire, Rome boasts nearly 3,000 years of architecture, history, and culture. 

After arriving at one of Rome's airports, you'll transfer to your hotel in the historic center. Settle in and relax, then head out for a stroll and your first look at the Eternal City. Your next few days will involve lots of sightseeing, so check out some of Rome's landmarks and sites. 

For an authentic market experience stop by the Mercato dei Fiori, where locals shop for fresh vegetables, a wide selection of flowers, meats, and cheeses. Browse for authentic Italian pasta and other souvenirs then take a break with coffee and a pastry at one of the many cafes surrounding the market. 

Day 2: Vatican & Classic Tour of Rome

St. Peter's Square and the Vatican
St. Peter's Square and the Vatican

Today you will visit the Vatican City museums and Sistine Chapel, as well as other top sights for an exclusive 6-hour tour of the city's incredible art and history. Start at the Vatican, where you'll visit the Pio Clementio Museum, Gallery of the Candelabra, Gallery of Tapestries, and Gallery of the Geographical Maps

Continue to see the magnificent Raphael Rooms, ending in the breathtaking Sistine Chapel and St. Peter's Basilica. Experience the magic of Renaissance art as you learn about the secret details and untold stories of the masterpieces. 

Afterward, continue into a city for a tour of the city's most notable landmarks. Cross Piazza della Repubblica to see the Fountain of the Nyands, then continue to see the Trevi Fountain, La Colonna di Marco Aurelio, and the Palazzo di Montecitorio, which was designed by Bernini.

Admire the exterior of the Pantheon and head inside for a look at the ancient Roman temple, then head to Palazzo Madama—the Senate seat—ending at Piazza Navona.

End your evening with a stroll to the neighborhood piazza for gelato and some people watching.

Day 3: Private Colosseum & Forum Tour - Cooking Class

The ancient Roman Colosseum
The ancient Roman Colosseum

In the morning meet your archaeologist guide and dive into the history of the Roman Empire with a private guided walking tour of the Colosseum, the world's largest amphitheater (tickets included). You'll explore the main complex, as well as the Belvedere, the recently opened third ring with a view of the arena and the Imperial Forums up to the fourth and fifth rings. 

Walking through the ancient amphitheater is like taking a trip back in time to the days of the Roman Empire. At its prime, the Colosseum held 50,000 spectators and was the central venue for gladiator fights. Learn about some of ancient Rome's most famous and illustrious citizens, such as Julius Caesar, Emperors Augustus and Nero, and the Flavian Emperors who built the Colosseum. 

From here, continue to the Roman Forum and Palatine Hill, built between 46 BCE and 113 CEC. Walk along the ancient Roman street Via Sacra to see the Temples of Vesta, Antonino, and Faustina. See the ancient Basilica Julia and Aemilia and experience the grandeur of the Roman Empire.

Enjoy some time to yourself, then, in the afternoon, head to a cooking class to learn to make traditional Roman pasta specialties. You'll make Cacio e Pepe, Carbonara, and Amatriciana—all Italian favorites. Start with a combination of great local ingredients (pecorino cheese, fresh meat, and eggs), then make the perfect sauce with fresh market vegetables. Form the homemade dough into the classic pasta shapes and combine everything for a delicious meal. 

Once you're finished, sit down to enjoy your creations for dinner paired with the perfect glass of wine.

Day 4: Galleria Borghese - Free Afternoon in Rome

Exhibition of Bernini sculptures
Exhibition of Bernini sculptures

Today is a free day to explore the city. Head to Galleria Borghese, one of the world's premier art museums, for a self-guided visit to see works by extraordinary artists Bernini, Caravaggio, Canova, and Rafaello. The gallery's highlights include sculptures and paintings from Cardinal Scipione Borghese’s collection (1579 - 1633). 

Admire Caravaggio's most important paintings, including "Boy with Basket of Fruit", and see Bernini and Canova's sculpture collection, boasting works such as "Apollo and Daphne" and "David". Rafaello's "Entombment of Christ" is also a must-see. 

Walk through the ornate rooms and explore the splendid frescoes, stories, and masterful techniques behind the masterpieces. End the tour with a peaceful stroll around the Villa Borghese gardens, enjoying its beauty and calm far from the chaos of the city. Please note that although this is a self-guided tour, a guided option is also available. 

In the evening head back to the Trastevere neighborhood for dinner at an osteria or a trattoria, followed by drinks at a trendy wine bar.

Day 5: Transfer to the Amalfi Coast

Welcome to Amalfi
Welcome to Amalfi

It's time to say a bittersweet farewell to Rome. Not to worry, however, as you're leaving for equally green pastures on a high-speed train south to Naples. Located on Italy's southwestern coast, this city is famous due to its proximity to Mount Vesuvius and the ruins of Pompeii, as well as for being the birthplace of pizza.

In Naples, you'll transfer a couple of hours further south to the jewel of southern Italy: Amalfi. This 31-mile (50-km) stretch of coastline is renowned for its exceptional beauty, medieval fishing villages, endless lemon groves, and sprawling summer villas clinging to steep cliffs that run down to the sparkling azure waters of the Mediterranean.

Day 6: Capri and Anacapri Day Tour

Busy port on Capri
Busy port on Capri

Spend the day enjoying the sunshine and clear blue waters of Capri Island. Known locally as the "Pearl of the Mediterranean," the ancient Greeks called it the "Isle of Sirens." Capri sits on the south side of the Gulf of Naples and has been a popular vacation destination for millennia. The ancient Romans, in fact, built summer villas here for the Empire's VIPs.

In the morning, you'll head out for a scenic drive along the Sorrentine coast to the Port of Sorrento, where you'll catch a hydrofoil to Capri. From here you'll enjoy a guided walking tour of the island's attractions. Visit the Marina Grande and Marina Piccola harbors, walk along the Belvedere of Tragara (a villa-lined promenade with panoramic views), and explore the ruins of ancient Roman villas.

Then head up the hill to Anacapri see the Piazzetta and Augustus' Garden, and enjoy the best views of the Faraglioni Rocks. Should you choose, you can later return to the water and explore the Grotta Azzurra, the famous "Blue Grotto," which is located inside a hollowed sea cave. Afterward, perhaps spend the remainder of the afternoon soaking in the sunshine on the beach.

Day 7: Free Day on the Amalfi Coast

Enjoy your day on  the Amalfi Coast
Enjoy your day on the Amalfi Coast

Today you have free to explore and enjoy the leisurely coastal pace of life. Maybe go for a walk on the Lemon Path in the town of Minori or try your hand at windsurfing or kayaking near the shores of Praiano. You can see artisanal ceramics manufacturers in the town of Vietri, and go for a half-day hike on the Path of the Gods. Or simply laze on the beaches of Positano, Vettica Maggiore, and Centra

For dinner head to a family-run restaurant for the best Italian pizza paired with a glass of the perfect local wine.

Day 8: Fly From Naples to Palermo - Pick up Rental Car

View over Palmero at sunset
View over Palmero at sunset

Parting is such sweet sorrow, but it's time to leave the Amalfi Coast. Not to worry, because you'll be catching a flight from Naples to another Italian hotbed of culture and beauty: the island of Sicily. After a one-hour flight, you'll touch down in Palermo, on Sicily's northern coast, and pick up your rental car. You'll then drive 45 minutes into the city and to your hotel for check-in. 

You can discover Palermo right away on a self-guided walking tour. Sicily's regional capital boasts incredible and historic architecture spanning the Roman, Byzantine, Arab, and Norman eras. This commingling of cultures has also informed the culture, music, and cuisine of Palermo.  

The best place to begin your self-guided tour is Palermo's historic center. Its medieval streets are easy to navigate by foot, and there are many attractions and restaurants within walking distance. To get your bearings, take a passeggiata (stroll) along the narrow Via Maqueda, a pedestrianized thoroughfare that connects the north of the city to the south. A good place to start is the Fontana Pretoria, a Baroque fountain in the Piazza Pretoria.

Day 9: Guided Tour of Palermo - Visit Monreale

View of the cityscape from the Palermo Cathedral rooftop
View of the cityscape from the Palermo Cathedral rooftop

In the morning you will meet your guide for a private half-day tour of the Sicilian capital. 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'll 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, you might consider driving a short way 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). This 12th-century UNESCO Heritage Site is made up of ornate cloisters and gold mosaics featuring 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 abounding with citrus trees.

Day 10: Drive From Palermo to Marsala - Visit Erice

Castello di Venere in Erice
Castello di Venere in Erice

This morning you'll drive two hours west along the coast to the medieval town of Erice. Perched on a cliff that offers magnificent views, Erice is famous for its winding streets, stone archways, and decorated courtyards. Enter by the Porta Trapani, then walk to the historic city center and the 14th-century Duomo. Follow the ancient city walls and visit 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, drive one hour south along the western edge of Sicily toward Marsala, taking in the stunning views of the salt pans that edge the sea. Dotted with historic windmills and saltwater lagoons, these salt flats create a chessboard pattern evoking an otherworldly landscape. Spend a little time walking the pathways that run the length of the dry seawater basins 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. There is more to this charming town besides touring wineries (which is highly recommended). 

Day 11: Explore Marsala & Wine Tasting - Drive to Agrigento

Marsala Cathedral in the main square
Marsala Cathedral in the main square

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, drive two hours 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 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).

Day 12: Drive From Agrigento to Syracuse - Guided Tour of Valley of the Temples

Temple of Concordia
Temple of Concordia

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. 

After breakfast you'll explore Agrigento and its popular UNESCO World Heritage archaeological site, the Valley of the Temples, a ridge that's home to well-preserved ancient Greek temples. Here you'll meet an expert guide to walk through the ancient city of Akragas. You'll visit the temples of Hera, Concordia, and Herakles as your guide reveals historical insight that brings the ruins to life. You'll also learn how these ridge-top temples once served as beacons for homecoming sailors

Afterward, you'll drive 2-3 hours east to the island of Ortygia, the historical heart of the city of Syracuse, and check into your hotel. Sometimes called Città Vecchia (Old City), Ortygia is an easily walkable area full of treasures waiting to be discovered. Perhaps begin with a walk around the island before ducking into the network of narrow and winding alleyways, passing churches and baroque palaces as you go. You can't go wrong here, as everything is a visual treat.

Day 13: Explore Syracuse - Day Trip to Noto

View over Noto and its cathedral
View over Noto and its cathedral

Take the day to immerse yourself in historic Syracuse, a UNESCO World Heritage Site. Renowned for its rich Greek history, culture, architecture, as well as the birthplace of engineer and mathematician Archimedes, Syracuse was long regarded as one of the major powers in the Mediterranean. 

Spend the morning exploring the ancient ruins of the Neapolis Archaeological Park. Or lose yourself in Ortygia's winding streets, visiting tucked-away gems like the 19th-century Palazzo Impellizzeri, the Temple of Apollo in Piazza Pancali, or go underground to the San Giovanni Crypt and Catacombs, which date to the 6th century. Alternatively, for some relaxation, you can sunbathe next to turquoise waters at Arenella Beach, just 20 minutes south of Syracuse.

In the afternoon, you'll drive 45 minutes to Noto and explore this postcard-perfect baroque city. In a couple of hours, you can easily cover the town on foot. Stroll Corso Vittorio Emanuele and walk beneath Porta Reale (Royal Gate), taking in the embellished architecture at every turn, like the Chiesa di Santa Chiara, and end your walk at the spectacular 18th-century limestone Noto Cathedral. Optimize your Noto experience with a rewarding granita (frozen dessert) from the popular Caffè Sicilia.

Day 14: Day Trip From Syracuse to Ragusa Ibla, Modica, & Scicli

Ragusa Ibla
Ragusa Ibla

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 they were rebuilt in the Sicilian Baroque style.

First, drive 1.5 hours west to the hilltop town of Ragusa Ibla. You can meander the narrow lanes of its historic center, stopping to relax in a café or gelateria. If you're up for it, climb the 250 steps to the 18th-century Duomo di San Giorgio, a great example of baroque style. For more exercise, head up the stairs to Ragusa's upper town for breathtaking views. Alternatively, you can take a ride on the trenino (little train) from the Piazza Duomo along the city streets.

About 30 minutes south of Ragusa Ibla is Modica. Built on the sides of a canyon, this city is known for its artisanal chocolate. Wander its labyrinthine streets through Modica Bassa (Lower Modica), where you'll find many restaurants amid elegant 18th/19th-century buildings. Follow the alleyways up to medieval Modica Alta (Upper Modica) and Pizzo Belvedere for stunning views over the Modica Valley. Don't miss Duomo of San Giorgio, Modica's main church and a UNESCO landmark.

If there's time, travel south (20 minutes) to the ancient town of Scicli. You can stroll its pedestrianized Via Penna for nice views of nearby baroque palaces and churches, or visit one of its most beautiful baroque buildings, the Palazzo Beneventano, located on nearby Via Duce d'Aosta. If there's time, take the zig-zagging path up to the 19th-century San Matteo Church. Perched on a cliff, it affords sweeping vistas of the town below. You can also visit an old cave settlement in the Chiafura district. 

Day 15: Syracuse to Taormina - City Tour

View of Mt. Etna from the Greek theater
View of Mt. Etna from the Greek theater

After breakfast head out for the 1.5-hour transfer to Taormina, a sophisticated and popular resort town located up the coast from Syracuse, on the Ionian Sea. The town's amazing views and ancient theater, which is often used for operatic and theatrical performances, make it the perfect destination for fans of the arts. 

In the afternoon go for a three-hour guided walking tour of the city. Highlights include the 10th-century Palazzo Corvaja, named after one of the city's most influential families, the restored 17th-century Catholic Santa Caterina Church, and the Vicolo Stretto—the narrowest street in town. 

Skip the line to see the Greek theater, which boasts views of Mt. Etna and Giardini Naxos. From here head to the main square of Piazza IX Aprile to rest and refresh with a glass of Mt. Etna's famous wine at a local enoteca.  

Day 16: Guided Mount Etna Hike - Wine Tasting

Mount Etna's colorful landscape
Mount Etna's colorful landscape

Get an early start today and head 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 stretch out to the Mediterranean.

Hop back in your rental car and set out to tour the countryside, stopping at a Sicilian winery to sample the regional reds, whites, and rosés. You'll drive past fruit orchards, vineyards, and lava streams, then stop at various wineries to taste local wines, made from grapes grown on the nutrient-rich volcanic earth. Enjoy Sicilian delicacies of cheeses and salamis for lunch.

Day 17: Drive From Taormina to Catania - Fly to Rome

Via Etnea and Mount Etna
Via Etnea and Mount Etna

After breakfast, make the hour drive south to Catania. Sicily's second-largest city next to Palermo, Catania sits at the foot of Mount Etna and deserves a little exploration if there's time before catching your departure flight. Depending on traffic, it typically takes 15 to 20 minutes to travel from Catania's center to the airport. Best to arrive at least two hours prior to your international departure (and with some extra time to drop off your rental car).

Day 18: Goodbye, Italy

Farewell, Italy
Farewell, Italy

After one last cappuccino over breakfast, head to the airport for your connecting flight home. Have a good trip!

Map

Map of Rome, Amalfi Coast, & Sicily - 18 Days
Map of Rome, Amalfi Coast, & Sicily - 18 Days