Exploring Sicily: John Clifford’s Journey

John Clifford is a member of iBestTravel’s A-List, a collection of the top travel advisors in the world, and can help plan your perfect getaway. Below is an example of the type of itineraries he creates: a weeklong sojourn through Sicily. To work with John, contact him at John@InternationalTravelManagement.com.

Day 1: Catania

You will be picked up at the airport in a luxury Mercedes Sprinter with an English-speaking driver and taken to your hotel in Taormina, Grand Hotel Timeo, A Belmond Hotel.

Grand Hotel Timeo is known as one of Italy’s most glamorous retreats. The first hotel built in Taormina, it sits in a perfect location, directly in front of the Greek Theatre. Guestrooms combine elegance and charm. Let Sicily come to you as you admire its gardens, savor sensational local cuisine, and relax out on the Literary Terrace where generations of celebrated guests have gathered in the sun.

Day 2: Castello di Reschio

You will be picked up by Minivan (Viano, Vito or Similar) and your guide will help you explore Taormina and Castelmola. Admire the legendary Greek theater, remarkable both for its incredible state of preservation and for its breathtaking view of the Gulf of Naxos and Mount Etna, and discover the antiquarium, where Greek inscriptions testify to the city’s ancient origins. Head to the nearby village of Castelmola.

There, in a bar in the picturesque Piazzetta del Duomo, enjoy a taste of the celebrated local almond wine and delectable Sicilian sweets. Suggested restaurants include Tischi Toschi (typical Sicilian cuisine), Rosso Di Vino (seafood specialities), and Osteria Nero d’Avola.

Day 3: A Walking Tour of Siracusa and Ortigia

Visit the remarkable Greek remains of Siracusa, including the Temple of Apollo, which later became a Byzantine church and then an Arab mosque; the impressive Greek theater; and the fabled Fountain of Arethusa. Next, stop for an amazing lunch at a historic “Salumeria” located in Ortigia, tasting typical Sicilian products (cold cuts, cheeses and “caponata”). Stroll through the city’s picturesque winding streets and elegant piazzas, and admire the treasures on the island of Ortigia—Syracuse’s historical center—including its great cathedral, built on the Athena Temple, medieval and Baroque buildings.

At the end of the visit, transfer to Noto and accommodation at your hotel, Country House Villadorota. Tonight we suggest to dine at the hotel restaurant. Nested on the gently rolling hills of Noto, in the Sicilian countryside, Country House Villadorata sits on an organic farm planted with hundred-year-old olive trees, almond trees, citrus and vineyards cultivated according to biodynamic methods.

Day 4: A Bike Tour Of Palazzolo and Noto

Your cycling guide meets you in Palazzolo Acreide (a 30-minute drive) for a 2-3 hour relaxed biking tour, with stops along the way to admire and take photographs of the stunning views. Begin in Palazzolo Acreide, on a slightly downhill slope, to Testa dell’Acqua, and then, further downhill, cycle to Noto Antica, the ancient town of Noto, which was completely destroyed in the devastating 1693 earthquake.

Continue to the Monastery of Madonna della Scala, enjoying the spectacular landscapes of the Hyblaean Mountains. After passing the Salitello Bridge, you continue to modern-day Noto—named a UNESCO World Heritage Site and called the “Stone Garden” for its many gorgeous architectural masterpieces of the 18th-century Sicilian Baroque style. Our suggested restaurant is Manna.

Day 5: Drive a Fiat 500 Through Agrigento

Today you will enjoy a drive in a meticulously restored Fiat 500 from the 1970s, along the little streets of the historic center of Agrigento, a city described by Pindaro as the most beautiful among mortals. Our professional driver will assist you in driving the historic car, or he will drive for you so you can enjoy the views. During the tour, you will be able to stop to take pictures, buy souvenirs, and taste Sicilian delicacies.

After lunch, visit the wonderful Valley of Temples. As one of the premier Italian destinations, it is easy to forget that Sicily was once a thriving Greek colony. Once in Agrigento, explore one of the best-preserved relics of the island’s “Magna Graecia.” As English author and historian Douglas Sladen once said, “If you want to understand ancient Greece, come to Sicily.” Indeed, history tells us that there were once more Greeks living in the colonies of southern Italy and Sicily than there were Greeks actually living in Greece.

The Valley of the Temples has one of Magna Graecia’s best preserved temple complexes. You’ll hear the amazing story these eight temples tell and will visit the almost entirely-intact Temple of Concordia, as well as the Temple of Hera that suffered in a medieval earthquake.

You will overnight at Azienda Agricola Mandranova, an olive oil estate set in a garden of palm trees and African plants.

Day 6: Segesta and Erice

Today, you will head to Segesta for a guided tour of the temple and the theatre. Later, you will visit Erice, a wonderfully preserved medieval hill town at the extreme north-west corner of Sicily, on the top of Monte San Giuliano. The town overlooks the city of Trapani and the lower western coast towards the Egadi Islands, where sea salt is made, offering a breathtaking view. On a clear day, you can see the African coast.

You will see the Norman Castle and the Duomo as you walk through the cobble-stoned streets of the town, taking in the fresh air and a variety of aromas emanating from the numerous pastry shops for which Erice is known. In fact, you will stop to visit Maria Grammatico’s famous pastry shop to see the variety of sweets she lovingly creates. For lunch, we recommend Bye Bye Blues.

Tonight, you will stay at Villa Igiea, a Rocco Forte Hotel. Villa Igiea offers you a luxury hotel experience in a sumptuous villa right on the Palermo coast. The beautiful flowering garden boasts a swimming pool with stunning sea views, a spacious sun terrace, and a tennis court.

Day 7: Palermo and Monreale

Your last day begins with a tour of the Capo Market to select ingredients for a cooking class. Your guide will show you how to find and buy fresh foods to cook with alla Siciliana. At the end, you’ll enjoy all the dishes that you made together. The menu, of course, changes according to seasonality and ingredient availability, but it will always include an antipasto, a primo (first course) or a secondo (second course), a dessert, and Sicilian wine. The lesson lasts about 4 hours.

In the afternoon your guide will take you on a tour of Palermo. Founded by the Phoenicians in the 7th and 8th centuries B.C., the city was then under Arab rule for several centuries, leading to a period of immense prosperity. You will be enchanted by the city’s wide boulevards, traditional Sicilian Old Quarter, and baroque palaces. You will then visit the city’s main sights, including the Norman section, Quattro Canti, and the 12th-century Duomo.

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