You can do a lot with the traditional two-week vacation. Case in point, it's enough time to jaunt to southern Italy and tour beautiful locales like Naples, Pompeii, the Amalfi Coast, and the island of Capri. You'll even have time to road trip around the island of Sicily, enjoying incredible street food and touring ancient Greek ruins as you do.


  • Tour the ruins of Pompeii and hike up Mount Vesuvius
  • Escape to the island of Capri, playground for ancient Romans
  • Cool off by the Pretoria Fountain in Palermo
  • Visit ancient Greek and Roman ruins at Agrigento and Syracuse
  • Dine on fresh seafood in sophisticated Taormina

Brief Itinerary

Day Highlights Overnight
Day 1 Welcome to Naples! Naples
Day 2 Naples City Tour Naples
Day 3 Naples to the Amalfi Coast - Pompeii and Mount Vesuvius Amalfi
Day 4 Capri and Anacapri Day Tour Amalfi
Day 5 Free Day on the Amalfi Coast Amalfi
Day 6 Boat Tour of Grotta dello Smeraldo Amalfi
Day 7 Fly From Naples to Palermo - Pick up Rental Car Palermo
Day 8 Palermo Street Food Tour Palermo
Day 9 Drive From Palermo to Agrigento - Stop in Monreale Agrigento
Day 10 Drive From Agrigento to Syracuse - Guided Tour of Valley of the Temples Syracuse
Day 11 Explore Syracuse - Day Trip to Noto Syracuse
Day 12 Drive From Syracuse to Taormina - Mount Etna Hike Taormina
Day 13 Cooking Class in Taormina Taormina
Day 14 Drive From Taormina to Catania - Departure  

Detailed Itinerary

Day 1: Welcome to Naples!

Backlit street in Quartieri Spagnoli
Backlit street in Quartieri Spagnoli

Welcome to Italy! You'll arrive at Naples Airport and transfer to your accommodation in the city center. Naples sits on a bay near the still-active Mount Vesuvius, which buried nearby Pompeii in 79 ACE. There's a lot to see and do here, so make the most of your time in Naples.

In the evening, you could go for a stroll along the Caracciolo e Lungomare di Napoli, a waterfront promenade, then head to the Quartieri Spagnoli, a lively commercial hub, for dinner at a trattoria. On the way stop at the Toledo Metro station, the Stazione della Metropolitana dell'Arte, to see beautiful mosaic inlays.

Day 2: Naples City Tour

Aerial view of Naples
Aerial view of Naples

Naples has been continuously settled for millennia. The city is renowned for its art, architecture, food, and religious frescoes. Its historic city center enjoys UNESCO World Heritage designation, and Naples' many historic sights attract visitors worldwide. You'll visit these landmarks on a three-hour guided tour of the city.

Notable highlights include the 17th-century Palazzo Reale (home to a museum and two theaters), the centrally-located Piazza del Plebiscito, the Teatro di San Carlo (one of the Royal Palace's theaters), the beautiful Galleria Umberto (a massive 19th-century glass-roofed shopping mall), and the Basilica di San Francesco, which was built as a tribute to the emperor. The Castel Nuovo (a fortress protecting the port), 13th-century Duomo, Via Toledo shopping district, and historic Spaccanapoli Street are also popular destinations. 

Naples is also famous as the birthplace of pizza, and the city's music culture has strongly influenced opera and folk music standards.

Day 3: Naples to the Amalfi Coast - Pompeii and Mount Vesuvius

Ancient street in Pompeii
Ancient street in Pompeii

In the morning you'll leave Naples and head south to the Amalfi Coast. However, you'll be stopping for a full-day group tour of the area's most notable attractions, Pompeii and nearby Mount Vesuvius.

It begins with a visit to the ruins of Pompeii, once a flourishing Roman coastal city that was famously buried under ash and volcanic debris after the eruption of Mount Vesuvius in 79 ACE. The ash, which killed many of Pompeii's residents, acted as an archaeological time capsule by preserving many of the city's original buildings completely intact. 

You'll stroll the remains of Pompeii's ancient streets, which are lined with well-preserved villas, shops, public buildings, and plazas. Afterward, you'll stop in a local workshop to see the production process for various regional handicrafts, such as cameos and coral jewelry. 

After a break for lunch, it will be time to visit Mount Vesuvius, which is designated as a UNESCO Biosphere World Reserve. It's a brisk 30-minute hike up a trail to the top, where you'll be rewarded with stunning views inside the crater as well as panoramic views of the surrounding landscapes and the Tyrrhenian Sea

After the excursion to Vesuvius, you'll continue on to the Amalfi Coast, where you'll check into your hotel and settle in for the evening.

Day 4: 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 5: 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.

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Day 6: Boat Tour of Grotta dello Smeraldo

The Emerald Grotto
The Emerald Grotto

In the morning, you'll embark on an hour-long tour of one of the most beautiful natural attractions in Amalfi, the Grotta dello Smeraldo (Emerald Grotto). You'll transfer down the coast to the fishing village of Conca dei Marini, which lies just east of the town of Praiano. The scenery on the drive is stunning, with the famous lemon groves of Amalfi on one side and the azure waters of the Mediterranean on the other. 

Upon arrival in Conca dei Marini, you'll hop in a boat that will take you to the grotto, which is located inside a cave. Like the Blue Grotto on the island of Capri, the color derives from an underground opening in the cave that lets light in and creates the namesake green color effect. As you pass under the hanging stalactites and stalagmites, you'll see these emerald colors shimmering off the surface of the water. The Grotta dello Smeraldo is one of the lesser-visited tourist sights in Amalfi but certainly one of its most beautiful.

Day 7: 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 8: Palermo Street Food Tour

Street vendor sells pastries
Street vendor sells pastries

One great way to experience Palermo is on a street food tour. You'll snack your way through the city's historic streets while visiting back-alley markets, modest bakeries, old bars, and various food stalls while on the hunt for sweet and savory eats.

You'll meet your guide in the morning and meander over to the Vucciria and Capo markets. These two open-air markets are so abuzz with activity that they're reminiscent of Arab souks. You'll discover how Sicily’s unique culinary history informs its street food scene as vendors of local produce and seafood proffer their goods.

Throughout, you'll visit bakeries, cafés, and food stalls to try a variety of popular Sicilian street snacks: pani câ meusa (sesame-flavored bread stuffed with fried veal and spleen), panelle (chickpea fritters) and arancini (deep-fried balls of rice stuffed with meat, vegetables, and cheese). Wash it all down with sweet Sicilian wine before digging into a seasonal dessert like cannoli (deep-fried pastries filled with sweetened ricotta cheese), gelato, or a refreshing granita (a fruity semi-frozen treat).

Day 9: Drive From Palermo to Agrigento - Stop in Monreale

The celebrated Monreale Cathedral
The celebrated Monreale Cathedral

Get an early start and make the 30-minute drive to the town of Monreale. Here, 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 World Heritage Sitel features ornate cloisters and gold mosaics depicting 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. It offers a beautiful view over the Conca d'Oro, a fertile valley abounding with citrus trees.

From here, continue driving 2.5 hours to Agrigento, a hilltop city on Sicily's southwestern shore. After checking into your hotel, you can head out and explore. Stroll through Agrigento's densely-packed historic center to Via Atenea, a busy thoroughfare lined with shops, restaurants, and bars. From Via Atenea, climb your way upwards through a maze of cobblestoned narrow alleys and side streets past 18th and 19th-century palazzi (estate homes).

Day 10: 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 11: 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 12: Drive From Syracuse to Taormina - Mount Etna Hike

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

The day begins early with a two-hour drive up the coast and inland to Europe's largest active volcano, Mount Etna. You'll arrive at Rifugio Sapienza, Etna's southern access point, and prepare for a guided hike. After organizing your equipment, you'll ride a cable car up 9,500 feet (2,900 meters) to Torre del Filosofo, the last accessible lookout point before the summit. Enjoy the breathtaking scenery that includes solidified lava flows, smoke fumaroles, and wide vistas that stretch out to the Mediterranean.

After Etna, you'll continue driving 1.5 hours to Taormina, a sophisticated resort town located on the Ionian Sea. It's famous for gorgeous coastal views and its ancient  Greek theater, the Teatro Antico di Taormina, which is still used for opera and theatre performances. You can also visit the 17th-century Catholic Santa Caterina Church and stroll along the Vicolo Stretto, the narrowest street in town.

Day 13: Cooking Class in Taormina

A local market in Taormina
A local market in Taormina

You're in for a treat, as today you'll partake in a private cooking class. In the morning, you'll meet your chef instructor at a local market for a guided tour. You'll stop at fruit and vegetable vendors to pick up seasonal produce before heading to the fishmonger to choose the freshest catch of the day.

After the market tour, you'll retire to a professional kitchen for your hands-on cooking class. Over a couple of hours, you'll prepare a full Sicilian menu complete with a traditional dessert. Afterward, you'll sit down and enjoy lunch comprised of the foods you prepared in class. Of course, the meal will be paired with local wines. 

Day 14: Drive From Taormina to Catania - Departure

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 the airport at least two hours prior to your international departure (and with some extra time to drop off your rental car).


Map of Naples, Amalfi Coast, & Sicily - 14 Days
Map of Naples, Amalfi Coast, & Sicily - 14 Days