Luxury Southern Italian Escape: Sicily, Amalfi Coast & Capri - 14 Days

Highlights

• Step into ancient history with a private tour of Agrigento's Valley of the Temples
• Wander a vineyard and taste volcanic wines on the slopes of Mount Etna
• Sample local Sicilian cuisine and produce with a market tour in Catania
• Spend a day zipping along the Amalfi Coast on the back of a Vespa
• Explore the islands of Capri, Ischia, and Procida by private yacht

Brief Itinerary

Detailed Itinerary

Day 1: Arrive in Palermo, Explore the Sicilian Capital

Buongiorno and welcome to Sicily, the sunkissed island at the toe of Italy's boot. You'll land in Palermo, the island capital, where you'll collect a rental car and drive to your luxury accommodation in the historic center. Palermo is a lively and energetic city that blends Arab, Norman, and Baroque influences, which you can see in its food and architecture. The old streets, filled with grand palaces and historic monuments, are a sensory feast, and this afternoon you'll explore the sights, sounds, and flavors on a self-guided adventure.

Start in the historic center, where Palermo's medieval streets are easy to navigate on foot. Do as the Italians do and take a passeggiata (stroll) along the narrow Via Maqueda, a pedestrianized thoroughfare that connects the north of the city to the south. Then you could also explore art at the Stanze al Genio tile museum and Palazzo Abatellis, see a performance at Italy's largest opera house, the Teatro Massimo, or haggle for lunch or vintage clothing at Mercato Ballarò, Palermo's largest open-air food market.

Day 2: Day Trip to Erice & Trapani: Salt Pans & Marsala Wine Tasting

Today you'll drive two hours west along the coast of Sicily toward medieval Erice. Perched on a cliff, Erice offers incredible views and is famous for its winding streets, stone archways, and decorated courtyards. Walk through the Porta Trapanito to explore the historic city center, the 14th-century Duomo, and the 12th-century Norman fortress, the Castello di Venere. After, cruise down to Trapani, a seaside town at the foot of Mount Erice and the gateway to the Aegadi Islands. Explore monuments and churches in the Old Town, and find somewhere special for lunch.

Afterward, continue deeper into the Marsala region for a taste of the region's renowned salt and wine. This corner of Sicily is famous for both things, and you'll spend an hour exploring the local salt pans, where small mountains of salt are harvested to create watercolor scenes straight out of a painting. Continue to a special private wine tasting among the vineyards at an ancient baglio, a large Sicilian farmhouse estate. If you time it right, you'll experience a magnificent sunset over the offshore islands before returning to Palermo for the evening.

Day 3: Drive to Agrigento via Monreale

Set off across the island this morning, driving from Palermo on the north coast to Agrigento on the south. Along the way, you'll stop to discover a UNESCO World Heritage Site that's considered the greatest example of Norman architecture in the world. Pull up in the town of Monreale, 30 minutes from Palermo, to see the 12th-century Cattedrale di Monreale, which features ornate cloisters and gold mosaics depicting scenes from the Old and New Testaments. After, continue another 2.5 hours to Agrigento, a hilltop city on Sicily's southwestern shore.

After checking into your 4-star 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 cobblestoned narrow alleys and side streets past 18th and 19th-century palazzi (estate homes). Return to the center and take your pick of the local restaurants for a relaxed dinner.

Day 4: Guided Tour of Agrigento's Valley of the Temples

The highlight of any trip to Agrigento is a visit to the Valley of the Temples. This UNESCO World Heritage Site is the star attraction, dotted with well-preserved Greek temples, including the Temple of Concordia, one of the best-preserved Doric temples in the world. Today, you'll explore the archaeological site with a private guide, who will lead you on a journey through the ancient city of Akragas, bringing to life stories of the past. Marvel at the temples of Hera, Concordia, and Herakles while learning about the region's rich history.

After, you could explore the Museo Archeologico Regionale Pietro Griffo, which holds a rich collection of artifacts from Akragas, or head to the coast and take a boat tour and see the stunning white cliffs of Scala dei Turchi.

Day 5: Drive to Taormina via Villa Romana del Casale 

This morning, you'll drive three hours from Agrigento to Taormina, pausing at the elaborate UNESCO-protected Villa Romana del Casale en route. A local guide will lead you through the villa, showing you some of the world's best-preserved and varied Roman mosaics at this house built for Ancient Rome's elite. Afterward, get back on the road toward Taormina, skirting around the active Mount Etna volcano on the final stretch. Pull into this gorgeous Sicilian town that blends ancient sights with natural beauty, and check into your luxury hotel. 

In the early evening, venture over to the Greek Theatre of Taormina, a fascinating historical monument carved out of the hard rock of Mount Taurus in the third century BCE. From up here, you'll be treated to incredible views over the Ionian Sea and Mount Etna, so feel free to stay for sunset and enjoy nature's show before finding dinner in town.

Day 6: Free Morning in Taormina, Mount Etna Wine Tasting

Enjoy a leisurely morning in Taormina. After a slow breakfast at the hotel, you could walk across the spit of land to Isola Bella and discover the 17th-century palace, gardens, and fishing village. Or venture a little farther afield to see the medieval castle and narrow, hilly streets of Castelmola, a small village 3 miles (5 km) north of Taormina. For a relaxed beach day, head to Taormina Mare, an impressive stretch of rocky coastline with many lidos (public beaches), restaurants, and cafés. Grab a scoop of gelato and take a passeggiata along the seafront promenade to relish the laid-back spirit of la dolce vita.

Day 7: Day Trip to Catania: Food & Folklore Experience & Sightseeing Tour

After a light breakfast, drive 45 minutes south to Catania, an ancient port city at the foot of Mount Etna. Here you'll dive into Sicilian food and folklore with a local guide at the city's rowdy central market. Over the next hour, you'll taste the specialties of Catania, including locally grown almonds and pistachios, arancini with cuttlefish ink, local Piacentinu Ennese DOP cheese, and salami Sant'Angelo. At the final stop, you'll savor local treats like Sicilian caponata, eggplant parmigiana, Catanese salad, horse meatballs, and mini cannoli before saying goodbye to your host.

In the afternoon, meet a private guide for a more comprehensive tour of Catania. Discover the fascinating history and sites of this gorgeous coastal city as you wander along charming streets. Hear stories about the past, Catania's culture and gastronomy, and see the main landmarks, such as the Cathedral of Saint Agatha, the Castello Ursino, and the ancient Teatro Romano. Learn about composer Vincenzo Bellini, explore the labyrinth of botanical gardens at Villa Bellini, and watch plumes of smoke rise from Mount Etna while hearing about how eruptions have shaped the city. 

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

Your bellissima vacanza continues today as you head back to Catania, drop off your rental car, and catch a one-hour flight to Naples. Upon arrival, a private driver will collect you and take you to the Amalfi Coast, with a special stop at the archaeological site of Pompeii en route. Once a thriving and sophisticated Roman city, Pompeii was buried under a thick layer of ash after the eruption of Mount Vesuvius in 79 CE and lost for 1,500 years. A stroll along these ancient streets reveals preserved villas, shops, public buildings, and plazas.

From Pompeii, it's another hour along winding roads to reach the town of Amalfi. The Amalfi Coast is famous for its lush landscapes, lemon groves, terraced vineyards, warm hospitality, and fresh seafood, and the town of Amalfi is a great base. After settling into your luxury hotel, this afternoon is yours to explore your way. Spend your time discovering the town's winding streets, embrace the slower pace of life with a walk on the Lemon Path in Minori, or go on a mission to see the illuminated sea cave Grotta dello Smeraldo.

Day 9: Explore the Amalfi Coast by Vespa

Today is yours to explore the Amalfi Coast on two wheels, with an experienced private driver zipping you around the coast on the back of a colorful Vespa. Feel the wind in your hair as you cruise around one of the most storied and beautiful parts of Italy, making your way from Amalfi to Sorrento, a luxurious coastal retreat with a long history dating back to Ancient Rome. Notable Romans were the first to build seaside villas here, and the city introduced paper production, compass, and sea codes to Europe.

Then, ride along a spectacular serpentine road into coastal Positano, a steep and colorful village that cascades down into the sea. Spend some time exploring the narrow staircases and alleyways as you take in the sights, then stop for lunch at a beautiful terrace and enjoy seafood with views of the sea. Afterward, a half-hour trip takes you back to Amalfi, where the fun began. Your driver will share some details about how this town was once a prime destination for Europe's literati and aristocracy before you part ways.

Day 10: Amalfi Lemon Groves Tour & Cooking Class

The Amalfi Coast and lemons go hand-in-hand, and today, you'll explore this citrusy world with a private food tour and cooking class. Start with a scenic transfer to a lemon farm, where you'll tour the property and wander through lemon groves filled with Sfusato Amalfitano lemon trees. See the farmers hard at work, either in the field or the laboratories, preparing lemons for various products such as the famous limoncello, lemon jam, and lemon honey.

You'll get to taste all three products and then visit a local museum devoted to rural culture and arts and crafts, where you can learn about the evolution of farming here over the centuries. After an educational morning, tie on an apron and enter the kitchen. Here, surrounded by lemon groves and with views of the Amalfi Coast, you'll prepare a handful of dishes and a traditional pasta using local vegetables—and lemons, of course. Once your authentic Amalfi meal is ready, sit down in the garden and enjoy your feast, finishing with a little more traditional limoncello!

Day 11: Boat Transfer to Capri, Explore the "Isle of Sirens"

After breakfast, soak up the beauty of the Amalfi Coast one last time on your way to the port. Here, you'll boat a private boat destined for the island of Capri. The hourlong ride offers sweeping views back toward the coast, giving you a whole new perspective on the landscape as you cruise out to the island. Upon arrival, check into your luxury hotel and enjoy a relaxed lunch at an upmarket seaside restaurant. 

The afternoon is yours to explore as you wish. Capri is famous for its world-class shopping, so make time to visit some of the chic boutiques located in town. For a breathtaking panorama, take a funicular to the beautiful Gardens of Augustus. For sunshine, spend time by the sea or by the pool with a good book and a spritz. As the day winds down, savor a delicious dinner at a waterfront restaurant.

Day 12: Cruise Capri's Coastline by Private Yacht 

Today you'll set sail across the turquoise waters of the Mediterranean in style with a full-day excursion on your own private yacht. Cruise past Capri's coastline of dramatic cliffs and hidden coves, anchor in secluded bays for refreshing swims, and dive into the sea with a snorkel to explore the world beneath. Marvel at the iconic Faraglioni rock formations and glimpse the legendary Villa Malaparte from the sea. Pause to see the famous Blue Grotto, a natural wonder renowned for its ethereal glow.

Continue navigating the coastline in the afternoon, stopping to discover various landforms and gems, such as Coral Grotto, where vibrant marine life thrives beneath the waves. Capri is dotted with flamboyant villas and lush gardens best seen from the water, and you'll get a glimpse of gems like the imposing ruins of Villa Jovis, once the imperial residence of Tiberius, and stop by other luxe villas. As the sun begins its descent, enjoy a relaxed aperitivo of sparkling wine and fresh fruit on deck as you cruise back to port.

Day 13: Day Trip to Ischia & Procida by Private Yacht

Spend another day on the water with a private yacht tour to the neighboring islands of Ischia and Procida. Ischia is the largest island in the Gulf of Naples, and legend has it Ulysses landed here among its lush volcanic landscapes. Discover Castello Aragonese, a fort city on its own islet, and uncover hidden grottoes from the water. Wander the exotic La Mortella Gardens, and go for a swim from the beach at Maronti or the more secluded Punta Caruso.

Stop to savor a delicious lunch at a traditional restaurant in Borgo Sant'Angelo. After, hop over to Procida, the island made famous by 20th-century writer Elsa Morante's "Arturo's Island." Here, colorful homes cover the volcanic crater, and the islet of Vivara (a protected nature reserve) offers unique flora and abundant wildlife. At the end of the day, your captain will return to Capri.

Day 14: Boat Transfer to Naples, Depart

Your southern Italian sojourn comes to an end today. After breakfast, wander down to the port and take a private boat transfer to Naples. The journey takes approximately two hours. On arrival, a private driver will transfer you to Naples Airport in time for your departing flight home or onward. Safe travels!

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