Sicily Private and Small Group Guided Tours

With the magnificent Mount Etna and an inescapable ancient Mediterranean landscape, this eternally beautiful island is ripe for discovery.

Centrally located and the largest island in the Mediterranean, Sicily is unlike anywhere else. Formerly home to Greek, Arab, Norman, Byzantine and Aragonese empires; stepping through the cities of Palermo, Agrigento, and Syracuse impress with their antiquity. From ancient structures scattered throughout the Valley of the Temples to the stunning Mount Etna dominating the Sicilian landscape, it soon becomes apparent how layered this island’s history is. Walking through the UNESCO World Heritage Site of Monreale to Palermo’s bustling markets, it’s no wonder time in Sicily seems to flow at its own pace. Allow Context to help you discover the island's endlessly rich history on our Sicily private tours.

8 hrs • Sicily, Italy

Palermo (and Monreale) in a Day, with Context

La Martorana, Palermo Cathedral, Capo Market, Immacolata Concezione, Santa Caterina, Piazza Verdi, Piazza Pretoria, Piazza Bellini, Quattro Canti, and Cathedral of Monreale

8 hrs • Sicily, Italy

Mount Etna and Sicilian Wine Full-Day Tour

Mount Etna and Local Winery

Looking for something special?

Sicily custom tours and trip planning starting at $960.

Go Custom

4 hrs • Sicily, Italy

Savoring Sicily: Palermo Street Food Tour

Capo Market, Immacolata Concezione, Ballaro Market, and Santa Caterina

4 hrs • Sicily, Italy

Agrigento Half-Day Tour: Valley of the Temples

Valley of the Temples and The Griffo Museum

4 hrs • Sicily, Italy

Syracuse: Introduction to Ortigia and the Neapolis

Neapolis, Piazza Duomo, Apollo Temple, and Fountain of Arethusa

4 hrs • Sicily, Italy

Introduction to Palermo

Porta Carini, La Martorana, Palermo Cathedral, and Cappella Palatina

5 hrs • Sicily, Italy

Mount Etna Half-Day Tour

Mount Etna

3 hrs • Sicily, Italy

Introduction to Taormina

Piazza Duomo, Porta Catania, Palazzo Corvaja, Greek Gymnasium, and Porta Messina

3 or 3.5 hours • Sicily, Italy

Sicily Tour for Kids

Neapolis, Piazza Duomo, Apollo Temple, Fountain of Arethusa, Valley of the Temples, Capo Market, Oratory of Santa Cita, Piazza Marina, and Your choice of sites

Interested in exploring Sicily’s multifaceted history? Join a Sicily private guides: art historians, archaeologists or local experts, on our signature Sicily private tours. Lasting from three hours to six or more days and designed specifically for private groups, joining a Context's Sicily tours will surely leave a remarkable impression on your journey through this stunning part of Italy. Visiting Sicily for the first time? Get acquainted with Palermo’s main sites, history, and neighborhoods with our Introduction to Palermo walk. For a comprehensive view into Sicily through the ages, our Half-Day Agrigento explores some key archaeological sites located in the Valley of the Temples. A bite to eat? We invite you to explore Sicily’s unique and vibrant culinary traditions and volcanic flavors that will entice you to discover the depth and splendor of Sicilian food. Interested in immersing yourself in natural beauty? Try our Mount Etna Sunset Tour to learn about one of Sicily’s most iconic landscapes. Looking for an in-depth examination of Sicily for families? Our Sicily for Families tour is designed to engage young learners about Sicily’s history and culture. Need Context to sort out all the tours on your trip, from Palermo to Ortigia and everywhere in between? Our Multi-Day and custom experiences which can be entirely tailored to your interests.