Gary Portuesi's 14-day Trip Around Sicily

Marina, Palermo, Sicily, Italy
Photo: Holger Leue/Getty Images

Gary Portuesi is a member of Travel + Leisure’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. To work with Gary, contact him at

Day 1: Palermo

Arrive at Palermo Airport and meet with your private driver. Transfer to your hotel in Palermo. Arrive and check into Grand Hotel Villa Igiea.

In the afternoon, meet with your private driver and private guide in the lobby and start your tour of Palermo. Sightseeing includes the Cathedral, Palazzo dei Normanni, Quattro Canti, Piazza Pretoria, and La Martorana.

Day 2: Monreale & Ceflau

Meet with your private driver and guide in the hotel lobby and depart for Monreale. Arrive and start your tour of “The City of Mosaics,” including the iconic Cathedral and Clositers.

In the afternoon, you will arrive in Cefalu and start your walking tour of the city center with your private guide including the imposing Norman Cathedral and charming waterfront with typical Sicilian fishing boats.

Return to Palermo in the late afternoon. Your evening is open.

Day 3: Segesta, Erice, and Trapani’s Salt Pans

Meet your driver after breakfast for your transfer to Verdura Resort in Sicacca. On the way, stop in Segesta for a private tour of one of antiquity’s most fascinating ancient cities. Learn who the Elimi were and how this city was connected to Erice, which you will visit later in the day.

After the visit, proceed to Erice, the mysterious medieval town linked to the ancient Elimi people, and built on the ruins of an ancient city, with breath-taking views of the Mediterranean Sea (you can see the tip of Africa on a crystal-clear day). Your guide will have you stop at world-renown Maria Grammatico’s pastry shop for a tasting.

After your visit of Erice, you will stop at the Sea Salt Museum and learn how Trapani’s famous sea salt is made today, with reminders of yesterday’s process all around you in the form of Medieval windmills.

You’ll arrive at the Verdura Resort in late afternoon and check into your rooms. Your evening is open. For dinner, we recommend one of Verdura’s casual restaurants (trattoria style Liola or Amare for seafood) or the Resort’s fine dining establishment, Zagara.

Day 4: Selinunte and Planeta

Meet your driver and depart for Planeta’s flagship winery, Ulmo in Sambuca di Sicilia, for a visit of the vineyards, winery, and wine tasting with lightlunch. The Planeta cousins are a young, dynamic trio of winemakers who have adopted the notion of avant-garde winemaking in Sicily, eschewing the traditional methods, but embracing the ancient varietals and making high quality wine that has won numerous awards in the past 20 years.

After your winery experience, your driver will take you to Selinunte, Europe’s largest archaeological park. Meet your private guide at 3:00 p.m. for an exhilarating visit of some of the most interesting Greek ruins in the Mediterranean basin. You will visit the temples, some partly reconstructed, as well as the acropolis. You will have the ability to wander the ancient streets and walk into public buildings and homes.

Return to Verdura Resort after your visit of Planeta. Your Evening is open.

Day 5: Agrigento

Meet your driver in the hotel lobby and depart for Agrigento. Arrive and check into Hotel Villa Athena.

In the afternoon, your driver will take you to Mandranova for an olive oil tasting and lunch. Mandranova is a world-class operation, which sells its liquid gold toEataly, among other gourmet stores in the US. Learn about the different olive varietals used in the making of their superior olive oil and enjoy a delicious lunch.

After lunch, you will meet up with your guide to start your visit of the Valley of the Temples, one of the most important archaeological parks in the world and a UNESCO World Heritage site.

Day 6: Pizza Armerina and Noto

Check out of your hotel and meet your driver in the hotel lobby. On the way to Noto, stop in Piazza Armerina for your guided visit of Villa del Casale’s Roman mosaics, one of the most important sets of Roman mosaics in Antiquity.

Continue to Noto after your visit of Piazza Armerina. Arrive and check into CountryHouse Villadorata. Your evening is open.

Day 7: Modica and Ragusa

Meet with your private driver in the hotel lobby and head to the stunning Baroque cities of Ragusa & Modica, two of the three major UNESCO World Heritage Cities in the area.

Your first stop will be Ragusa. Consider lunch at Il Duomo or Locanda Don Serafin. Continue to Modica after lunch. Enjoy a chocolate tasting at Bonajuto. You will be back to Noto in the late afternoon.

Day 8: Siracusa

Meet your private driver in the hotel lobby and depart for Siracusa.

Once in Siracusa, meet with your private guide at the Archeological Park’s ticket point. Siracusa was considered the largest and most important Greek city in the Sicilian colony, and history has left behind some amazing ruins including the Temple of Athena, which was incorporated into the main Cathedral, whose Baroque façade betrays what lies within. On the island of Ortigia, walk the narrow streets of the Giudecca (the ancient Jewish quarter), and discover the site of the synagogue and the mikva the Jewish ritual bath, which lies eleven meters below ground level - the oldest in Europe.

Stop for lunch in Ortigia. After lunch, return to Noto with your driver. Your evening is open.

Day 9: Salina

Your private driver will pick you up at the hotel lobby to transfer you to Milazzo. Arrive and board your hydrofoil for the island of Salina. Your hydrofoil will likely make stops in Vulcano and Lipari before arriving at Salina (Santa Marina, the main port on the island). When you get on the hydrofoil, your driver will call your hotel, Capofaro, to arrange transportation to pick you up at the marina in Salina at your arrival. The rest of the day is at your leisure.

Day 10: Salina & Lipari

Your private excursion by boat around the island of Salina and Lipari begins in the morning. Your driver will pick you up and take you to the marina to meet your captain.

Enjoy the breathtaking coastline of Salina before proceeding to Lipari, the capital of the Aeolian Islands. Enjoy lunch in this bustling port town before cruising around the island. Your captain can drop anchor in remote coves and bays and you can jump in for a swim. Afterwards, return to Capofaro and enjoy dinner under the stars with the very talented Chef Ludovico’s spectacular cuisine.

Day 11: Salina

Today is your final day in the Aeolian Islands. You will spend it exploring Salina, the setting for the film, Il Postino.

In the morning, meet your private guide and driver in the hotel lobby and start your excursion around the island, stopping at various spots to enjoy the views, history, and flora and fauna. The late afternoon and evening is at your leisure.

Day 12: Taormina

Arrange for your hotel to transfer you to the marina for your hydrofoil ride to Milazzo. Arrive in Milazzo and meet with your driver for your transfer to Taormina. Arrive and check into you’re the Belmond Grand Hotel Timeo.

The rest of your day is free in Taormina. Enjoy the incredible views of Mt. Etna or walk the main street, Corso Umberto, and enjoy the many stores, pastry shops, cafes, and restaurants on your own.

Day 13: Mt. Etna

Meet your private driver and escort in the hotel lobby and depart for your excursion to Mt. Etna by jeep.

Visit the volcano’s craters before heading down for your winery experience at Cottanera winery.

Day 14: Departure

Your driver will pick you up in front of the hotel lobby for your private airport transfer to Palermo Airport.

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