Explore southern Italy in style on this relaxing, 17-day odyssey through Sicily and the Amalfi Coast. Starting in Palermo, you'll visit ancient ruins in Agrigento, go wine tasting on Mount Etna, and discover the stylish resort town of Taormina. Back on the mainland, the sun-soaked Amalfi Coast beckons—with lots of free time to explore its clifftop villages and lemon groves before sailing to Capri. Cruise the island's enchanted coastline by private yacht, then hop over to neighboring Ischia and Procida for a memorable day trip.

Highlights

  • Relax on the shores of the Ionian Sea in Taormina
  • Sample Sicilian street food in the bustling markets of Catania
  • Soak up the sun on the glittering Amalfi Coast
  • Explore Capri's colorful grottoes & hidden coves on a private yacht
  • Sail to the postcard-perfect islands of Ischia & Procida

Brief Itinerary

Day Highlights Overnight
Day 1 Welcome to Palermo! Palermo
Day 2 Day Trip to Erice & Trapani, Marsala Wine Tasting Palermo
Day 3 Transfer to Agrigento via Monreale Agrigento
Day 4 Tour the Valley of the Temples Agrigento
Day 5 Tour the Villa Romana del Casale, Transfer to Taormina Taormina
Day 6  Explore Taormina, Etna Winery Tour & Tasting Taormina
Day 7 Day Trip to Catania: Food & Folklore Tour & Discover the City Taormina
Day 8 Fly to Naples, Transfer to Amalfi Coast via Pompeii Amalfi Coast
Day 9-12 Free Days on the Amalfi Coast Amalfi Coast
Day 13 Transfer to Capri Capri
Day 14 Luxury Yacht Tour of Capri Capri
Day 15 Free Day on Capri Capri
Day 16 Private Yacht Trip to Ischia & Procida  Capri
Day 17 Transfer to Naples & Departure  

Detailed Itinerary

Day 1: Welcome to Palermo!

Views over Palermo's rooftops

Welcome to Sicily! Start your adventure in Palermo; the regional capital boasts beautiful Mediterranean weather and a long and storied history with Roman, Byzantine, Arab, and Norman influences. This mix of cultures is reflected in Palermo's architecture, music, and cuisine. Upon arrival at the airport, you'll be picked up and driven to your hotel in the heart of the city to settle in. The rest of the day is yours to spend as you like.

The historic city center and medieval streets are easy to navigate by foot, with many attractions and restaurants within walking distance. 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 in Piazza Pretoria. Some other optional activities include:

  • See art at the Stanze al Genio tile museum and Palazzo Abatellis.

  • Catch a performance at the Teatro Massimo, Italy's largest opera house.

  • Haggle for your lunch or the perfect pair of vintage jeans at the Ballaro Market, Palermo's largest open-air food market.

  • Relax on Mondello Beach and enjoy the sand and beautiful crystalline water.

  • Spend a few hours in the Galleria Regionale, a 15th-century neo-Gothic castle, to see medieval and Renaissance artwork.
  • Explore the Museo Archeological Regionale to see one of the richest collections of Punic and Ancient Greek art in Italy and many Sicilian historical artifacts.
  • Go shopping for fresh seafood in the colorful Vallero Market.

Day 2: Day Trip to Erice & Trapani, Marsala Wine Tasting

Sunset over the salt ponds near Marsala

This morning you'll meet your private driver and transfer two-hours west along the coast to the medieval town of Erice. Perched on a rocky cliff that offers magnificent views over Trapani, the Aegadi Islands, and San Vito Lo Capo, Erice is famous for its narrow winding streets, medieval arches, and decorated courtyards. Enter the old city by the Porta Trapani, then walk to the historic city center to reach the 14th-century Duomo. Follow the old city walls for a panoramic viewpoint, then explore the city's Spanish neighborhood and the Castello di Venere. This 12th-century Norman defensive fortress houses ruins of a Roman spa and the temple of Venus. 

When you're ready, make the short trip down to Trapani. Shaped like a sickle, Trapani sits at the foot of Mount Erice, along the western tip of Sicily, and acts as a gateway to the Aegadi Islands. Settled in the 13th century BCE by the Elymians, its Old Town and port are easily walkable by foot and include many notable monuments and churches, most of which date back to the late medieval period or 17th and 18th centuries. 

Highlights include people watching from the cooling Fontana di Tritone (Triton's Fountain) that divides the older part of the city from the new, and visiting the Ciambra Palace (or Giudecca) in the historic Jewish quarter for an important example of 16th-century Sicilian architecture that blends three styles: Gothic, Renaissance, and Plateresque. Stroll along Corso Vittorio Emanuele, Trapani's main road, to take in the refined and ornate buildings, and walk to the water's edge to visit the Ligny Tower. Once built for strategic reasons, it now acts as an archaeological museum and a lookout over the Gulf of Trapani.

After lunch, you'll head south along the western edge of Sicily toward Marsala, taking in the all-encompassing vistas of the dazzling salt pans that edge the sea as you enter the Saline di Trapani. Dotted with historic windmills, saltwater lagoons, and mounds of harvested salt, the salt flats create a chessboard pattern evoking an otherworldly landscape. Spend time walking the tourist paths that run the length of the basins filled with slowly-evaporating seawater before continuing to an ancient baglio (winery) to learn more about the history of the Marsala territory and its famous fortified wine. Sample a varietal or two among the vineyards as you watch the sunset over the Egadi Islands
 
At the end of the day, your driver will return you to your hotel in Palermo for the evening.

Day 3: Transfer to Agrigento via Monreale

Duomo Monreale
The magnificent interiors of the Cattedrale di Monreale 

Get an early start today with a 30-minute transfer 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 Site features ornate cloisters and gold mosaics depicting Old and New Testaments scenes. 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.

A 2.5-hour drive takes you 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 upward through a maze of narrow cobblestoned alleys and side streets past 18th- and 19th-century palazzi.

Day 4: Tour the Valley of the Temples

Discover the Valley of the Temples on a guided tour

Today you'll visit another UNESCO World Heritage Site and one of Sicily's most impressive archeological highlights, the Valley of Temples in Agrigento. Here you'll meet your expert guide for a tour of some of the world's best examples of ancient Greek art and architecture. A highlight of the valley is the Temple of Concord, which was built between 440-430 BCE and was still in use for over a millennium later. It's an impressive site in nearly perfect condition, and its immaculately preserved Doric architecture is often compared to the Parthenon in Athens.

Stroll through the ancient city of Akragas with the option to spend time at the popular archaeological museum and stop to marvel at 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.

The rest of the day is free to spend exploring Agrigento at your leisure.

Day 5: Tour the Villa Romana del Casale, Transfer to Taormina

Villa Romana del Casale
Ancient mosaics at the Villa Romana del Casale
Your driver will pick you up this morning and head east across the island, stopping first at the elaborate UNESCO-listed 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. 
 
Get back on the road and continue east to reach 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. Get settled into your hotel, then take a tour of the city to discover its highlights, including 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 Mount Etna and Giardini Naxos views. From here, you'll head to the main square of Piazza IX Aprile to rest and refresh with a glass of Etna's famous wine at a local enoteca.  

Day 6: Explore Taormina, Etna Winery Tour & Tasting

Taormina
Taormina's beautiful coastline
Enjoy a leisurely day exploring Taormina on your own. Perhaps take the morning to walk across the spit of land to Isola Bella and discover the 17th-century palace, gardens, and fishing village. Alternatively, there's the medieval castle and narrow, hilly streets of Castelmola, a small village located three miles (5 km) north of Taormina. And if you're in want of a beach day, there's the Taormina Mare, an impressive stretch of rocky coastline with many lidos (public beaches), restaurants, and cafés. 

Cap the day with a scoop of gelato as you take a passegiata along the seafront promenade to enjoy the old gardens of the Villa Comunale.
 
In the afternoon, you can learn more about the unique Etna terroir with a visit to a local winery. Take a walk in the vineyard and discover the native varieties and organic farming techniques, climbing to an ancient millstone as you hear about the history of traditional winemaking. After visiting an underground cellar to see the volcanic subsoils and aging barrels, your visit concludes with a wine tasting accompanied by freshly baked bread and organic olive oil.   

Day 7: Day Trip to Catania: Food & Folklore Tour & Discover the City

Catania's bustling food markets
Today's day trip starts in the vibrant markets of nearby Catania, where you'll spend the day discovering Sicilian culinary traditions and local customs. Visiting the market's bustling stalls, you'll sample some of the region's finger-licking specialties, such as granita (a refreshing shaved ice), Sicilian brioche, local cheeses and olives, arancini (fried rice balls), cartocciata (a popular street food of dough wrapped around mozzarella cheese and other fillings), and much more. The tour finishes with a casual lunch of traditional Catania street food specialties, like caponata, parmigiana, and cannolo accompanied by local wine.
 

Continue your discovery of Catania with a two-hour private tour of this gorgeous coastal city. Stroll along the seaside, visit Duomo Square, explore the narrow streets of Old Town, and take in the views from 13th-century Ursino Castle. As you wander through the city's charming streets and alleys, you'll hear stories about the city's rich history, culture, and gastronomical traditions.

Beyond the main landmarks such as the Cathedral of St. Agatha and the ancient Teatro Romano, you'll see the labyrinth of botanical gardens at Villa Bellini and get a feel for the vibrant daily life of the modern city by witnessing the bustling fish market and the busy shops of Via Etnea. Watch the plume of smoke as it rises out of nearby Mount Etna, and hear about how eruptions and earthquakes have shaped Catania's history and landscape. 

In the afternoon, a transfer takes you back to Taormina, where the rest of the day is at your leisure.

Day 8: Fly to Naples, Transfer to Amalfi Coast via Pompeii

Coastal roads and villages along the Amalfi Coast

Bid Sicily a fond farewell this morning, as a transfer takes you to the Catania Airport to catch a short flight to Naples. Upon arrival, you'll be greeted by your private driver and make your way south toward the Amalfi Coast.

En route, you'll visit the ruins of Pompeii, a bustling seaside city that was buried underneath 13-20 feet (4-6 m) of ash and volcanic debris after the 79 CE eruption of Mount Vesuvius. The ash, which killed many of the city's residents, acted as an archaeological time capsule by preserving many of the city's original buildings and features completely intact. 

The city was lost for 1,500 years following Mount Vesuvius' eruption before its accidental rediscovery in 1599. Items of all kinds, from jars to furniture, were frozen in time, and even those unfortunate citizens of the empire, unable to flee the oncoming ash, were perfectly preserved. A stroll through Pompeii's ancient streets will show off preserved villas, shops, public buildings, and plazas, giving you an insider's look into life 2,000 years ago.

Continue the scenic drive south to reach the Amalfi Coast. With a natural beauty that has been drawing people to the region since ancient Rome, today, the mountains and sea cliffs are dotted with pastel confections of holiday homes and sumptuous villas, which have elevated the coastline to one of the most fabulous and unique destinations in the world. Its cultural landscape—churches, gardens, vineyards, and villages—is divided into thirteen different municipalities, which were listed as UNESCO World Heritage sites in 1997. 

Your base for the next five nights is in beautiful Sorrento. Get settled into your hotel, then take a stroll along the waterfront as you head to the Sorrento's central Piazza Tasso for dinner and drinks.

Days 9-12: Free Days on the Amalfi Coast

Sun loungers along the coast in Positano
The next four days are free for you to relax and immerse yourself in the beauty of the Amalfi Coast. Explore colorful clifftop villages, spend your day soaking up the sun at the beach, or discover more of the coastline with a boat tour. Other suggestions include:

  • Go shopping at the colorful Via San Renato street market, a weekly open-air market selling everything from clothes to household items to fresh produce and delicious cheeses.

  • Get lunch in Marina Grande Beach, Sorrento's fishing village famous for its seafood restaurants and volcanic sandy beach (the perfect place to relax after a delicious meal).

  • Tour the nearby coastal city of Salerno and the ancient Greek city of Paestum (the site contains some of the world's best-preserved Greek temples). 

  • Enjoy a private sommelier-guided wine tour of two prestigious estates in Campania's rugged Apennine Mountains.
  • Go for a walk on the Lemon Path in Minori or see the illuminated sea cave of Grotta dello Smeraldo.

  • Learn about the local ceramics manufacturing process in Vietri, or go for a half-day hike on the Path of the Gods

  • Visit the beautiful Villa Cimbrone and Terrace of Infinity in Ravello.

  • Soak in the sunshine on Gravitella Beach in Vettica Maggiore, Lannio Beach in Centra, or Arienzo Beach in Positano.

  • Try your hand at windsurfing in Praiano.

  • Rent a kayak and explore emerald green grottos, tiny hidden beaches, and impressive sea caves.

  • Enjoy a quiet day in the serene town of Atrani, far away from the hustle and bustle of the larger villages.

  • Visit the Cloister of San Francesco in Sorrento, an oasis of tranquility that's located steps away from the town's historic Sant'Antonino Piazza.

  • Enjoy unspoiled nature in the Ferriere Valley Nature Reserve, famous for its postcard-perfect fishing villages and striking countryside crisscrossed with hiking trails.

Day 13: Transfer to Capri

Colorful Port of Capri
The colorful port of Capri

Set sail for the "Isle of Sirens" today as your driver takes you to the port in Amalfi to board a private boat destined for the sunshine and clear blue waters of Capri. Known locally as the "Pearl of the Mediterranean," Capri sits on the south side of the Gulf of Naples and has been a popular vacation destination for millennia (even the ancient Romans built summer villas here for the Empire's VIPs).

Upon arrival, get checked into your hotel, then spend the rest of the day exploring. 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 to see the Piazzetta and Augustus' Garden and enjoy the best views of the Faraglioni Rocks.

Day 14: Luxury Yacht Tour of Capri

Yachts moored off Capri
Spend today on the water as a luxury yacht takes you on a full-day journey along Capri's magnificent coastline, stopping to explore hidden grottoes and caves, secluded beaches, and prime swimming spots. Passing limestone cliffs that rise dramatically from the sea, you'll sail to iconic Capri highlights like the Faraglioni Rocks, Tiberius' Leap, the Blue Grotto, and the Punta Carena Lighthouse, spotting the island's many spectacular and secluded villas along the way.

Day 15: Free Day on Capri

Views from Mount Solaro on Capri
Today is free to explore the wonders of Capri at your own pace—touring the island's ancient villas and gardens, hiking its many scenic coastal paths, or relaxing at the beach.

Day 16: Private Yacht Trip to Ischia & Procida 

The Beautiful Island of Ischia
The beautiful island of Ischia
Set sail again today for an unforgettable day trip to the charming islands of Ischia and Procida. Although less famous than their popular neighbor Capri, they offer just as much beauty with fewer crowds. Your first stop is Ischia, where you can explore Ischia Porto and Ponte and visit the imposing Castello Aragonese. This historic castle sits on an islet connected to Ischia by a narrow strip of land. After visiting the castle, relax over lunch at one of the nearby restaurants or head to the fishing village of Sant'Angelo, one of the most picturesque corners of Ischia.
 
Back onboard your yacht, it's time to head to Procida, one of Italy's most photographed islands. You may not recognize its name, but the endearingly iconic shot of Procida's Corricella Marina appears on several Italian guidebook covers. The marina's pastel bungalows have glistened over the Tyrrhenian Sea for generations, welcoming tired mariners after months at sea. The distinctly bright hues allowed anglers to spot their homes, even from great distances and in hazy weather.
 
For the past 3,000 years, Procida has been home to a strategic port, but it's become a popular filming location in more recent years. You may recognize Corricella Marina from "Il Postino" and "The Talented Mr. Ripley." Spend the rest of the day exploring Terra Murata, the historic center of Procida perched on the cliffs above the port of Corricella, and enjoy the sandy Chiaiolella Beach before sailing back to Capri for the evening.

Day 17: Transfer to Naples & Departure

Sunset over Naples
Your Italian odyssey draws to a close today as you enjoy a leisurely breakfast overlooking the Bay of Naples and say your goodbyes to Capri's enchanted shores. After a private boat trip back to Naples, you'll be met by your driver and transferred to the airport to catch your departing flight. Arrividerci!

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Map of Luxury Southern Italy: Sicily, Amalfi Coast & Capri - 17 Days
Map of Luxury Southern Italy: Sicily, Amalfi Coast & Capri - 17 Days