Sicily: Jewel of the Mediterranean with optional Sorrento Fall 2026

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Overview

Sicily: Jewel of the Mediterranean with optional Sorrento Fall 2026
Palermo, PA, Italy
Sep 24 - Oct 6, 2026
Wherever Tours image
Wherever Tours
$3,999
Deposit: $500

About this trip

Begin your Sicilian adventure in Cefalù, a charming coastal town known for its golden beaches and medieval streets. Spend a day in Palermo, a lively city rich in culture, cuisine, and history. Discover the hilltop town of Erice with its ancient charm, then explore Trapani’s scenic coastline and Marsala’s famous wines. Don’t miss Agrigento’s Valley of the Temples, a breathtaking UNESCO site of ancient ruins. Finally, unwind in Taormina, where boutique shopping and panoramic views of Mount Etna create a perfect blend of relaxation and beauty.

Optional 3-Day Extension: Head to Sorrento for a taste of the Amalfi Coast, with unforgettable day trips to Positano’s cliffside charm and Capri’s dazzling Mediterranean vistas — a perfect finale to your Italian escape.

What's included

Luxury Transportation

All ground transportation including airport transfers

Deluxe 4-Star Hotels

9 nights of hotel accommodations (12 nights with optional Sorrento add-on)

Guided Tours

English-speaking guides

Entrance Fees

To all included attractions

Included Meals

As specified on the itinerary

Wine Tastings

As specified on the itinerary

Cooking Classes

As specified on the itinerary

What's not included

Gratuities

For guides and drivers

Trip Insurance

Optional trip cancellation insurance

Optional tours

If offered

Airfare

Booked on your own (we can assist)

Day 0

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Wednesday, September 23, 2026

Departure from the USA!

Your journey begins as you depart from your hometown airport. Relax, and let the excitement build—tomorrow you’ll awaken in Palermo to start your adventure.

Day 1

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Thursday, September 24, 2026

Arrive in Palermo, Free time in Cefalù

Upon arrival at Palermo airport, you will be greeted by your Wherever Tours tour leader. A private transfer from the airport to the resort hotel in Cefalù will be provided for all. After checking into your hotel, take some time to unwind and enjoy the hotel's beautiful pool, stroll down to the beach, or simply relax in your room. A welcome reception will be held, featuring traditional appetizers and wine tasting.

This evening, you will have dinner at the hotel restaurant, showcasing delicious local cuisine and regional wines.

Sunset Hotel, Cefalú (D)

Day 2

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Friday, September 25, 2026

Tour of Palermo

This morning, take an exciting tour of Palermo, the vibrant capital of Sicily, which is rich with stunning ancient buildings, magnificent cathedrals, and beautiful gardens that tell stories of the past. Palermo is known for its many hidden treasures, such as the impressive Monreale Cathedral, a breathtaking example of Norman architectural style, which contains over two tons of gold mosaics that glimmer in the sunlight. After the tour, prepare yourself for a surprise.

This afternoon, enjoy some well-deserved free time back in the charming town of Cefalù, where you can explore at your own pace. Dinner is at your leisure, allowing you to savor local flavors.


Sunset Hotel, Cefalú (B)

Day 3

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Saturday, September 26, 2026

Erice, Trapani, Marsala


After breakfast, embark on a journey by luxury coach along the magnificent northern coastline of the stunning Tyrrhenian Sea, heading towards the town of Trapani. As we travel, we'll make a stop in the mountaintop town of Erice, where you'll view breathtaking panoramic views that are sure to leave you in awe. In the afternoon, we will arrive in Trapani, a town known for its picturesque salt flats and the striking Cathedral of San Lorenzo, a true architectural gem. Later, we'll make our way to Marsala, where we'll check into the Baglio Donna Franca Wine Resort, a beautifully preserved and restored baglio dating back to the 19th century.

Tonight, we'll take a tour of their winery, followed by dinner at the hotel's renowned restaurant, where you will have the opportunity to taste the region's most famous wines.


Baglio Donna Franca, Marsala (B, D)

Day 4

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Sunday, September 27, 2026

Segesta, Marsala, Cooking Class


Today, we'll visit Segesta, renowned for its breathtaking and well-preserved Greek temples that stand as a testament to ancient architecture. As you explore this historic site, take a moment to appreciate the beauty and significance of the surroundings. Afterward, indulge in a tasting of local appetizers paired with some of the exquisite specialty wines, showcasing the rich flavors of the region.

Tonight, enjoy a cooking class followed by dinner featuring the foods that you prepared earlier.

Baglio Donna Franca, Marsala (B, D)

Day 5

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Monday, September 28, 2026

Agrigento, Valley of the Temples


This morning, embark on a journey from the charming town of Marsala to the stunning city of Agrigento, nestled on the southern coast of Sicily along the beautiful Mediterranean Sea. Once you arrive, a local expert will guide you through the ancient treasures during a tour of the Valley of the Temples, which boasts structures dating back to the fifth century BC. This extraordinary archaeological site was rightfully added to the prestigious UNESCO World Heritage list in 1997, showcasing its significance and historical value.

After a day filled with exploration and discovery, return to the hotel for dinner, complemented by local wine.


Hotel Della Valle, Agrigento (B, D)

Day 6

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Tuesday, September 29, 2026

Caltagirone, Taormina


Today, we will head to the eastern shore of Sicily, where we will explore the picturesque seaside town of Taormina. As we travel, we make a stop in Caltagirone, renowned for its Baroque-style ceramics that reflect the rich artistic heritage of the region. Here, we will have the unique opportunity to visit the private home of the noble family, Pace Gravina. Giacomo, the owner, will welcome us into his magnificent palace and personally guide us through the incredible history of Sicilian nobility, sharing stories and insights. Once we finish the tour, he’ll host us for a lavish buffet lunch in the grand ballroom.

Finally, we will continue our journey to our luxurious seaside resort hotel, perfectly situated on the beach in Giardini Naxos, where you will enjoy a relaxing stay for the next four nights, soaking in the beauty of this destination.

Hotel Sant Alphio, Taormina (B, L)

Day 7

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Wednesday, September 30, 2026

Tour of Taormina, Greek-Roman Theater


After breakfast, we'll take the funicular up the mountainside to the picturesque village of Taormina. Once we arrive, embark on a captivating guided tour of the area, where you'll discover the stunning Greek-Roman Amphitheater, a historical site that offers breathtaking views.

After the tour, you’ll be free to explore a world of luxury shops and cafés, set against breathtaking vistas of the sparkling Mediterranean east coast—scenery made iconic by Season 2 of HBO’s hit series The White Lotus.

The evening is yours to enjoy. Feel free to explore the area’s restaurants and sample the local specialties.

Hotel Sant Alphio, Taormina (B)

Day 8

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Thursday, October 1, 2026

Mt. Etna, Zafferana


Start your day right with breakfast this morning, as today promises an exciting adventure to Mt. Etna, the tallest active volcano in Europe, known for its stunning landscapes. We’ll make a stop in the picturesque town of Zafferana, where you’ll get the unique opportunity to visit a local rosticceria, learning the art of making the famous arancini rice balls, a cherished Sicilian delicacy. Savor the flavors of exquisite cannoli, alongside a selection of other local foods and fine wines.

This afternoon, we’ll return to our seaside hotel in Taormina, where you can unwind and enjoy a relaxing evening, soaking in the beautiful surroundings.

Hotel Sant Alphio, Taormina, (B, L)

Day 9

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Friday, October 2, 2026

Free day, Optional excursion to Siracusa


Today, take some free time to either relax and unwind on the beautiful beach or by the inviting pool, or venture out to explore and shop in the charming streets of Taormina at your own pace. The choice is yours!

Tonight, immerse yourself in a culinary experience like no other as you enjoy a sumptuous dinner prepared by the renowned Sicilian chef, Cristian Foti. Enjoy plenty of exquisite wine flowing and local singers serenading you; this night will transform into a lively and festive party filled with joy and laughter.

Optional Experience:  An optional trip to the historic city of Siracusa will be offered by your tour leader.


Hotel Sant Alphio, Taormina, (B, D)

Day 10

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Saturday, October 3, 2026

Departure Day or Optional Extension in Sorrento

It's time to say avererderci to those leaving Sicily today. After breakfast, you will be transferred to the Catania airport. We hope that you had a wonderful time and that you'll consider traveling with us again.

To those embarking on the 3-day Sorrento extension, your tour continues.

After breakfast, we’ll depart Sicily and begin our journey to Sorrento. Along the way, we’ll enjoy a scenic ferry cruise across the Straits of Messina to reach mainland Italy. Our route includes a relaxing lunch stop in the picturesque region of Calabria, before continuing north.

Later in the afternoon, arrive at the Villa in Sorrento, overlooking the Gulf of Naples. Enjoy a delightful dinner accompanied by music, dancing, and wine.

Villa Giovanna, Sorrento (B, D)

Day 11

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Sunday, October 4, 2026

Isle of Capri (with optional Sorrento add-on)


Today, transfer by boat to the famous and beautiful island of Capri. A Wherever Tours representative at the hotel is available to offer any suggestions before your transfer so that you can make the most out of your day. This tiny island, once the playground of ancient emperors, will leave you breathless due to its limitless charm and historical sights. Take some time to shop and explore, and most of all, enjoy the spectacular views from above.

Upon your return, take some time to wander the streets of Sorrento before retiring to the hotel.


Villa Giovanna, Sorrento (B)

Day 12

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Monday, October 5, 2026

Positano (with optional Sorrento add-on)


This morning, head out to the Amalfi Coast, a UNESCO World Heritage Site. Have your cameras ready for a spectacular view of Positano, where you'll have free time to shop and explore this beautiful seaside town, featured in many famous movies and magazines. Later, enjoy your “ultima cena” (last dinner) in Sorrento. Great food, music, song, and dance will complete this unforgettable stay in Sorrento, creating memories that will last a lifetime.


Villa Giovanna, Sorrento (B, D)

Day 13

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Tuesday, October 6, 2026

Return Departure


Sadly, we must say “arrivederci” to Sicily and Sorrento. After breakfast, transfer from the hotel to the Naples airport for your onward journey. On behalf of all of us, thank you for considering Wherever Tours!


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Location

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1. Palermo, PA, Italy

Palermo, PA, Italy

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