Gems of Sicily

Gems of Sicily

Gems of Sicily

Gems of Sicily

Explore Italy's Cherished Island

Days: 10 | From: $7,700/per person

  • Enjoy accommodations at excellent boutique hotels in prime locations.
  • Curated tours with outstanding private guides: you’ll have an instant local friend with insider access.
  • Experience what has made Italy a traveler favorite for generations: extraordinary people, food, art, and history.

Dive into Italy's island of Sicily on this immersive 10-day itinerary. Beginning in Palermo and journeying through some of Sicily’s top highlights, you’ll explore ancient ruins, taste Sicilian staples, hike on the slopes of iconic Mount Etna, sample local wine, and get to know Sicily like the locals do.

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We tailor itineraries to your dates and interests, adjusting hotels, excursions and length as desired.

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At a Glance

  • Palermo
    2 nights: Sicilian cuisine, bustling markets, and priceless relics
  • Agrigento
    2 nights: ancient ruins and a look into Sicily's archeological past
  • Noto
    2 nights: wine tastings and picturesque seaside towns
  • Taormina
    3 nights: exploring in the foothills of Mount Etna

All itineraries are fully customizable. We will send you a personalized variation that reflects your interests and travel dates at no extra cost. Call to discuss your travel plans with one of our Specialists who know this region firsthand.

5-Star Reviews

Find out why our discerning travelers consistently rate us with 5-stars.

Sample Itinerary

Day 1: Arrive in Palermo

Palermo, Sicily town skyline with landmark towers at dusk.

Welcome to Italy! Upon arrival at the airport in Palermo on the island of Sicily, you’ll be privately transferred to your hotel for the next two nights. The rest of the day is yours to explore on your own, settle in, and dive into the Sicilian pace of life.

Accommodations: Palazzo Natoli , 2 nights

Palazzo Natoli is a modern and elegant boutique hotel consisting of 12 rooms located, with the exception of the Garden Apartment, the Family room and the Comfort room, in the main building of the hotel. These cozy accommodations represent the soul and style of Palazzo Natoli, which, with its location close to Palermo Cathedral and the Quattro Canti, is the perfect destination for discovering the city and enjoying a charming holiday in a luxury hotel.

Day 2: Palermo Food Tour and Duomo di Monreale

Mosaics in interior of Monreale Cathedral. Monreale, Sicily, Italy

Today you’ll explore Palermo and Monreale. Your day begins with a private guided food tour through the heart of Palermo, offering an authentic look at the city’s vibrant street life and culinary traditions. You’ll explore historic open-air markets such as Capo, Ballarò, and Vucciria—each one steeped in history and culture dating back to the Arab period. Visit bakeries, street vendors, and old inns, where you’ll sample classic Sicilian street food and experience local traditions firsthand.

In the afternoon, explore the stunning Duomo di Monreale, just a short drive from Palermo. Built in the 12th century by King William II, this architectural masterpiece showcases the height of Arab-Norman artistry. Inside, you’ll be captivated by expansive golden mosaics illustrating biblical scenes, while your guide provides context on the Duomo’s historical and religious significance. The visit concludes with a peaceful stroll through the adjacent Benedictine cloister, where carved columns and medieval sculptures offer a final glimpse into Sicily’s rich past.

Accommodations: Palazzo Natoli , 2 nights

*Includes: Breakfast

Day 3: Ruins of Segesta and Travel to Agrigento

The greek temple of Juno in the Valley of the Temples, Agrigento, Italy. Juno Temple, Valley of temples, Agrigento, Sicily.

Head from Palermo to Agrigento with a stop in Segesta along the way to see some of Sicily’s most remarkable archaeological sites.

In Segesta, you’ll explore ruins that reflect the region’s rich and layered history—from its Elymian origins and Greek architectural influence to its later Muslim and Norman presence. See the well-preserved Doric temple, set in a striking natural landscape of hills and vineyards, followed by the Acropolis, where panoramic views highlight the grandeur of the site and the surrounding countryside.

The tour concludes with a short walk through lesser-known but significant ruins, including one of the earliest Muslim mosques in Sicily and a Medieval fortress. This visit offers a unique perspective on the island’s cultural evolution before continuing your journey to Agrigento, where you’ll stay for two nights.

Accommodations: Mandranova Resort , 2 nights

Mandranova Resort is an elegant-yet-rustic lodge located in Agrigento. It mimics the feel of a traditional farmhouse and winery. The “gebbia”, formerly used for agricultural irrigation, has been transformed into a small but beautiful swimming pool where guests can cool off from the heat of the summer. The restaurant offers refined Sicilian cuisine prepared with home-grown and locally sourced produce. The hotel has a total of 15 rooms and suites featuring Sicilian antiques as well as modern amenities.

*Includes: Breakfast

Day 4: Archeology Tour and Agrigento Old Town

Il tempio dei Dioscuri or Temples of Castor and Pollux. The Valley of the Temples in Agrigento, archaeological heritage. Hellenic architecture in Sicily. August 2023.

Today you’ll enjoy a full-day excursion with an expert archeologist in Agrigento. Visit the Valley of the Temples, a UNESCO World Heritage Site and one of the most important archaeological parks in the Mediterranean. As you walk along the ridge, you’ll encounter the Temple of Herakles, the remarkably intact Temple of Concordia, and the remnants of the Temple of Zeus, including the enormous Telamon statues.

In the afternoon, the tour continues in the old town of Agrigento, once the acropolis of the ancient city. You’ll visit the Church of Santa Maria dei Greci, built over a Greek temple, and the Cathedral of San Gerlando, featuring an intricately carved wooden ceiling. At the nearby Diocesan Museum, you’ll find a collection of sacred art and historical artifacts.

A walk through the medieval streets leads you to the 13th-century Monastery of Santo Spirito. Here, you’ll also enjoy a tasting of handmade almond and pistachio sweets, prepared by the cloistered nuns using traditional recipes. The day concludes with a stroll down Via Atenea, Agrigento’s lively main street, and a visit to the Church of San Pietro.

Accommodations: Mandranova Resort , 2 nights

*Includes: Breakfast

Day 5: Villa Romana del Casale and Travel to Noto

Sunrise at the old baroque town of Ragusa Ibla in Sicily. Historic center called Ibla builded in late Baroque Style. Ragusa, Sicily, Italy, Europe.

Travel from Agrigento to Noto today via the historic town of Piazza Armerina for a tour of the renowned Villa Romana del Casale.

Located just outside the town center, this exceptional Roman villa is famous for housing the largest and most diverse collection of Roman mosaics ever uncovered. Built between the 3rd and 4th centuries AD, the villa once served as a luxurious rural estate for a high-ranking official. Your expert guide will walk you through its remarkably preserved rooms, including reception halls, private quarters, and thermal baths.

After your visit, continue to Noto and your hotel for the next two nights.

Accommodations: Gagliardi Boutique Hotel , 2 nights

Gagliardi Boutique Hotel is an 18th century palazzo with an intimate Sicilian history, located in the heart of Noto. It features a rooftop bar and terrace overlooking the old town, a shady garden and patio for outdoor dining, and chic, timeless rooms that channel Sicilian elegance.

*Includes: Breakfast

Day 6: Wine Tastings, Seaside Towns, and Sicilian Ruins

A motorboat sailing along the canal in Ortygia. Cityscape of the famous Sicilian town, Italy.

Today, you’ll spend a full day exploring the Noto countryside. Your day begins with a visit to a wine estate in the Val di Noto wine region. You’ll tour the vineyards and winery with estate staff, learning about the local winemaking process and grape varieties like Nero d’Avola and Grillo. The visit ends with a tasting of selected wines, paired with regional snacks such as cheese, olives, and traditional bread or pastries.

In the afternoon, enjoy a guided tour of Siracusa, starting at the Archaeological Park of Neapolis. Explore key sites including the Greek Theatre, Roman Amphitheatre, and the “Ear of Dionysius.”

Afterward, continue to Ortigia, Siracusa’s historic center. Walk through its narrow streets, visit the Cathedral of Siracusa and the Fountain of Arethusa, and enjoy free time to explore or have lunch by the sea. This visit combines history, culture, and local flavor in one enriching day.

Accommodations: Gagliardi Boutique Hotel , 2 nights

*Includes: Breakfast

Day 7: Catania Tour and Travel to Taormina

Beautiful view of Catania cruise port with smoking volcano Etna in the background.

Enjoy a private transfer from Noto to Taormina with a stop in Catania for a guided walking tour. In Catania, a private English-speaking guide will lead you to the city’s key historic and cultural sites. Begin in Piazza Duomo, home to the iconic Elephant Fountain, and continue to the Roman Theater, an impressive 2nd-century structure tucked within the city center.

The tour also includes food tastings in Catania’s lively markets, where you’ll sample traditional Sicilian street food and experience the city’s vibrant culinary scene. After the tour, continue your private transfer to Taormina.

Accommodations: Hotel Villa Angela , 3 nights

Villa Angela is a small and friendly boutique hotel in Taormina with only 27 rooms and an intimate atmosphere that makes every guest feel instantly at home. It's set in a stunning location above Taormina town center, with a spectacular panorama stretching from the crystalline waters of the Ionian Sea all the way to the top of magnificent Mount Etna. The property has a swimming pool, restaurant, and bar. Rooms come all with wi-fi, air conditioning/heating, furnished balconies, and breathtaking views.

*Includes: Breakfast

Day 8: Mount Etna and Wineries

Aerial view of Silvestri crater at the slopes of Mount Etna at Sicily, Italy

After breakfast, set off on a trip to the iconic Mount Etna. An off-road vehicle will take you past scenic Sicilian villages and Etna’s renowned wine-growing areas as you ascend the volcano.

Along the way, you’ll explore some of Mount Etna’s most striking landscapes, including ancient lava flows, forests, and craters during a relaxed 45-minute hike. A knowledgeable guide will provide insights into the volcano’s history, geology, and mythology. You’ll also visit a lava cave, equipped with a helmet and flashlight, to learn how these natural formations were once used for ice storage.

Your day continues with a visit to a local winery on Etna’s slopes. After touring the production facilities, you’ll enjoy a guided tasting of Etna DOC wines, known for their unique character shaped by the volcanic soil. A traditional Sicilian lunch follows, featuring regional specialties and local wine.

Accommodations: Hotel Villa Angela , 3 nights

*Includes: Breakfast, Lunch

Day 9: Free Day in Taormina

View of some columns in the stage of the greek theater in Taormina and a perspective of snowy mount EtnaView of some columns in the stage of the greek theater in Taormina and a perspective of snowy mount EtnaView of some columns in the stage of the greek theater in Taormina and a perspective of snowy mount Etna

Enjoy a full day to explore Taormina. Visit the Greek-Roman Theatre, one of the most dramatically located ancient theaters in the world, or walk the Via Teatro Greco to the peaceful Villa Comunale gardens to see a variety of native and exotic plants. Stroll through Taormina’s historic center, including a visit to the Cathedral and a stroll along Corso Umberto I, lined with shops, cafés, and lively squares.

Accommodations: Hotel Villa Angela , 3 nights

*Includes: Breakfast

Day 10: Departure

Say goodbye to Taormina and transfer to the airport to catch your departing flight.

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