Sicily Tour

“Highlights of Sicily”

our flagship SMALL GROUP TOUR

Explore Sicily's rich history, beauty, arts and culture. Walk among the world's best-preserved Greek ruins; hear ancient myths on the sites where they happened; marvel at Roman and Norman mosaics; explore hilltop villages; visit sites of Mafia and anti-Mafia activities; enjoy the cuisine of people who care intensely about flavor; relax for lunch at farms and wineries.

Join us in sharing unforgettable stories and insights we've gained in our decades of experience of showing Sicily to visitors.

“Highlights of Sicily” itineraries: Our schedule varies by season, but typically includes Siracusa, Noto, Modica, Ragusa, Piazza Armerina (Roman Villa), Agrigento, Selinute, Marsala, Erice, Segesta, Palermo, Monreale, Cefalù, Madonie Mountains, and Taormina. For details, please click here: winter & spring itinerary and summer & autumn itinerary.

transportation: our driver and van/minibus.

lodging & meals: we provide all accommodation and just over half the meals, allowing us to introduce you to a wide variety of the best Sicilian cuisine, while allowing you plenty of opportunity for you to explore restaurants on your own as well.

TOUR DATES IN 2024

Late Spring Tour: 27 April—07 May,

          May Tour: 19—29 May, with an option to see ancient tragedy or comedy in Siracusa’s ancient Greek theatre*.

special 2nd May “Highlights of Sicily” tour, 21-31 May, with an option to see ancient tragedy or comedy in Siracusa’s ancient Greek theatre*. Click here for itinerary

Early June Tour: 07—17 June, with an option to see ancient tragedy or comedy in Siracusa’s ancient Greek theatre*.     

Late June Tour: 18—28 June, with an option to see ancient tragedy or comedy in Siracusa’s ancient Greek theatre*.

          July Tour: 8—18 July. This tour is timed to land us in the spectacular Palermo Santa Rosalia Festival. If you’re a group of 6 or more, contact us us about this itinerary or other dates in July & August for other Sicilian summer festivals.

          Early September Tour: 06—16 September

          Late September Tour: 20—30 September

          Early October Tour: 04—14 October (full, waiting list only)

          Late October Tour: 18—28 October

          November Tour: 02—12 November (if you’re a group of six or more)

TOUR DATES IN 2025

Early Spring Tour: 22 March—1 April,

Easter Tour: 12—22 April (see description below)

          Spring Tour: 26 April—06 May, with an option to see ancient tragedy or comedy in Siracusa’s ancient Greek theatre*.

May Tour, 17-27 May, with an option to see ancient tragedy or comedy in Siracusa’s ancient Greek theatre*.

Early June Tour, 10-20 June, with an option to see ancient tragedy or comedy in Siracusa’s ancient Greek theatre*.

Late June Tour, 20-30 June, with an option to see ancient tragedy or comedy in Siracusa’s ancient Greek theatre*.

    July Tour: 07—17 July. This tour is timed to land us in the spectacular Palermo Santa Rosalia Festival. If you’re a group of 6 or more, contact us us about this itinerary or other dates in July & August for other Sicilian summer festivals.

          Early September Tour: 05—15 September

          Late September Tour: 19—29 September

          Early October Tour: 10—20 October

    *for Greek Theatre performances, tell us in advance if you are interested.

walking requirements:

Our lovely rugged island brings us often to steep uphill climbs or uneven, rocky, or cobblestone surfaces.

Travelers on our small group tours must be able to walk at least two kilometers on uneven ground and be able to climb three flights of stairs without stopping to rest.

Unfortunately, people with walking difficulties create unfair issues on group tours. Please, if you have difficulty walking, we'll be happy to schedule a private tour, tailored to your needs and at your pace.

For the fitness-conscious, we want you to be delighted to know that you will achieve your daily 10,000 steps on our tour.

“easter festivals of Sicily“ 2024 tour

No one does Easter Week (Pasqua) with as much deep feeling and colorful spectacle as the Sicilians. This is the beauty of high Catholicism with strong echoes of ancient pagan ritual. We will follow Easter Week festivals across Sicily, eat regional Easter delicacies, hear festive music, and visit the major tourist sites along the way.

Dates: 12—22 April, 2025

Length: 10 Days (day before Palm Sunday to day after Easter Monday)

Itinerary: Please click here for the itinerary. 

Cost: € 3370

“Tunisia TOUR”

The land we now call Tunisia once stood at the center of Mediterranean history as mighty Carthage, and then became the home of prosperous ancient Roman cities. It knew the glories of the Arab-Islamic Golden Age in great centers of learning like Kairouan andTunis. 

HISTORY: We begin our visit in Tunis, the site of ancient Carthage and one of the Mediterranean’s most vibrant Arab souks. Then we travel to several remote and sparsely visited Roman cities across the vast Sahel region that the Romans called “Africa”.  We’ll visit a startling Roman amphitheatre marooned from traveled ways, some medieval clifftop ksour, and modern Tunisian cities. In all we’ll visit seven of Tunisia’s UNESCO World Heritage sites.

CULTURE: We’ll descend into underground Berber dwellings used in Star Wars filming, cross dunes at the edge of the Sahara, and wander several sensory-satiating souks. Ever present as we travel through the country that began the "Arab Spring" will be the people themselves as they struggle to hold together their still-fragile democracy.

LAND: The well-watered coast, abundant in crops; the Sahel, where ancient cities once flourished and whose ruins now testify to human-caused climate change; and the Sahara desert, with some real dune landscape, not common elsewhere in the Sahara. 

dates: TBA.

promotional information: Before the pandemic disruption of its programming, these trips were offered under the aegis of Humanities West of San Francisco (https://humanitieswest.net/). That affiliation remains in anticipation of Humanities West’s resumption of full programs.

itinerary: click here for the most recent itinerary. Tour leaders are both Douglas Kenning of Sicily Tour and our Tunisia expert guide Ridha Benelhedi together.

price = in 2022, it was $ 3290, double occupancy.

Single Supplement: = $800 US

group size: 8-16.

“Jerusalem & Israel tour”

Here is the epicenter of world passion, of the riveting, furious engagement of the human heart with the divine.  We will spend eleven days in the cauldron of Western faith, exploring what happened here and why it matters to so many people.  We will be non-denominational, non-political, only advocates for and explorers of the phenomenon that is mankind,, that is us.  How we humans behave & misbehave is history, and nowhere is our history so fraught as in Jerusalem.

This visit will focus on what really is the eternal city, walking its streets, telling its stories, & doing day trips to Masada & the Dead Sea.  Then, for our final four days, we will explore further afield, visiting the Palestinian areas and circling counter-clockwise around Israel proper. Click here to look at an itinerary.

dates: 2023 TOUR CANCELLED (for sad but obvious reasons). Next Jerusalem TBA.

group size: 8~16

price: $ 3590

“THE GLORIES OF GREECE” tour

The Mother of Us All: This tour will focus on the civilizations of the Aegean from the decline of the Mycenaeans through the troubled triumph of Classical Greece, with an emphasis on developments in civic life & the narratives of history & myth. Here Western Civilization was born, a continuing, evolving miracle, that in our own time is becoming the World Civilization.

Archaic & Classical Athens: We begin climbing the Acropolis, wandering Agorà, & perusing the unimaginably wonderful Archaeological Museum. Then there will be a free day for you to explore as you like, with our recommendations in hand.

Peloponnesus & beyond: Then we're off to Eleusis to re-imagine the mysteries, kept secret for fifteen hundred years & still unknown. We will continue into the Peloponnesus, where Mycenaeans carried forth Minoan high culture until falling into dark centuries, out of which arose the “Golden Age of Western Civilization”.

We will envision ancient potters under the Corinthian acropolis; the Oresteia at Mycenae, Heracles at Tiryns; the military state at Sparta; the clarity of drama & healing at Epidaurus. The wild beauties of the Temple of Apollo at Bassae continue to amaze, & Olympia illustrates how sports is worship. Then, beyond the Peloponnesus, we pilgrimage up to the glorious spiritual heights of Delphi & Metéora & imagine the desperation of Thermopylae, before finishing again in Athens

Cultural life & landscape: Greece also offers fascinating modern culture & landscape, & our visit will include two nights in the charming 18C town of Nauplio, sleeping under the wild coastal beauty of Monemvasia, & crossing the ‘impassible’ Taiyetos Mountains.

In all, we’ll visit 8 UNESCO World Heritage sites, with an option on another. That is, optional excursions to Crete, Rhodes, & elsewhere can be arranged.

itinerary: email Douglas Kenning at dkenning@sicily-tour, or through the "Contact Us" page for the itinerary and other questions.

group size: 8~16

dates: TBD

price: TBA (in 2018 it was € 3217)

The other half of Italy:

“NAPLES AND THE MEZZOGIORNO” tour

Our tour takes us around the Mezzogiorno, which you can guess means “the middle of the day”, a.k.a. “noon”, and is the nickname for the half of Italy from Naples to the south, alluding to the powerful midday sun in this sun-drenched region (be reassured, we are traveling in mild October). Here is a region with utterly different history from northern Italy for three-quarters of the history of the Italian peninsula: ancient Greeks, Normans, Arabs, Aragonese, Spanish, all of whom ruled and shaped the culture of the Mezzogiorno, none of whom were in north Italy. Here you meet a half of Italy that seems a millennium older.

It is also the land of quiet mysteries, simpler life, and fewer tourists. Well, that is not true for the capital of the Mezzogiorno, Naples, a raucous, bustling, incredible place, embarrassingly rich in treasures. We will spend almost week immersed in Naples: the old town Spaccanapoli, including its Underground, one of the greatest archaeological museums in the world, two of the most famous Roman sites in the world (Pompeii and Herculaneum), the Amalfi Coast, and the astonishing “Versailles of the South” at Caserta, seat of Italy's richest post-Renaissance kingdom.  Our second week will be plunged into the countryside of the rest of the Mezzorgiorno, from the depths of incredible Matera, to delightful Trulli Houses, to the Baroque glories of Lecce, to remote hill towns and coasts. All along we will enjoy full measure of the best food in Italy (or so we claim in the Mezzogiorno).

Itinerary: click here for the proposed itinerary.

Dates: ca. 16—28 October, 2024

Cost: € 4775

Classes