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 2025

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

          Spring Tour: 26 April—06 May, with an option to see ancient tragedy or comedy in Siracusa’s ancient Greek theatre* (FULL, waiting list only)

May Tour, 17-27 May, with an option to see ancient tragedy or comedy in Siracusa’s ancient Greek theatre*. (FULL, waiting list only)

June Tour, 10-20 June, with an option to see ancient tragedy or comedy in Siracusa’s ancient Greek theatre*. (still small, intimate, so take advantage of the personalized size)

    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, check the I.N.D.A. Classical Drama website (https://www.indafondazione.org/en/) and tell us in advance if you are interested.

TOUR DATES IN 2026

Early Spring Tour: 14-24 March.

Easter Tour: 28 Mar-07 April (see “Easter Festivals” description below).

          Spring Tour: 18-28 April.

May Tour: 16-26 May, with an option to see ancient tragedy or comedy in Siracusa’s ancient Greek theatre*.

June Tour: 05-15 June, with an option to see ancient tragedy or comedy in Siracusa’s ancient Greek theatre*.

    July Tour: 08—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: 04—14 September

          Late September Tour: 25—05 October

          Early October Tour: 09—19 October

Late October Tour: 23 October—02 November

    *for Greek Theatre performances, check the I.N.D.A. Classical Drama website (https://www.indafondazione.org/en/) and tell us in advance if you’re 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“ 2025 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

28 Mar-07 April, 2026

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

Itinerary: Please click here for the itinerary. 

Cost: € 3995

“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: 24 Oct — 06 Nov, 2025

promotional information: As a preview to Douglas Kenning’s presentational style and approach to Carthage and Tunisia, look at this recording of a February 7, 2025 conference at the Commonwealth Club of San Francisco on “Hannibal’s Carthage,” hosted by Humanities West of San Francisco (https://humanitieswest.net/). Tour leader Douglas Kenning was one of the two presenters. A link to this talk is offered at no cost here: https://www.commonwealthclub.org/events/archive/video/humanities-west-presents-hannibals-carthage).

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 = double/twin room, double occupancy = $ 3,900 ($ US) or € 3,700. Single supplement = $ 800 ($ US) or € 750. Deposit to hold your place = $500 ($ US) or €470 / person.

group size: 8-16.

“Spain & Portugal” Tour

We will explore the heart of Hispania, the celebrated and amazing Iberian Peninsula. Her history runs through the Carthaginians, Romans, and Visigoths, to the unique glory of Judaism and Islam harmoniously together (the “convivencia”) during the Arab Golden Age; followed by the Christian Reconquista, giving us chivalric tales and leading to two world-striding empires (Portuguese and Spanish).

Our tour will take us on a circuit of central and southern Spain and then through southern and central Portugal, from Madrid, through Granada and Seville, to Lisbon and Porto, and a dozen delightful places in between. Look at the itinerary for all the stunning ancient and medieval sites and cultural centers we will visit.  We will dine at fine restaurants as well as find traditional local foods, and stay at hotels with traditional character. Download the itinerary to check out the details.  

dates: 15-30 May, 2025

group size: min. 6 — max. 16 participants.

price: Only 4 places left. Special discount special price of 4000 pp. Offer expires March 31.

“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 tour 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 the 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 mysterious. 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: Perhaps in autumn 2026. Contact us to put yourself on the notification list.

price: TBA

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 around the Bay of 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 itinerary.

Dates: 16—28 October, 2024 (full). Will be run again in October 2025. Contact us to put yourself on the notification list.

Cost: € 4775

Classes