Literary Sicily

(aka Shakespeare’s Italy II)

online classes: April 19 - May 12, 2027

travel: May 20 - 30, 2027

The coastline on the island-within-a-city of Ortigia, in Siracusa

Our new Adult Study Abroad program takes us to Sicily, the dreamy Mediterranean destination that’s the setting for at least two of Shakespeare’s plays, plus countless other texts from classical antiquity to the modern day. 

The idea for Literary Sicily started as an investigation into Shakespeare’s southern Italian plays, which include The Winter’s Tale, set in a nonspecific Sicilian city, and the well-loved comedy Much Ado About Nothing, which takes place in Messina, in the northeastern corner of the island. As we began thinking more about the Sicilian connections—including the fascinating (and dubious) theory that Shakespeare was a Sicilian man named Michelangelo Florio—we realized that we couldn’t discuss Shakespeare’s Sicily without also looking at the other literature that has helped form our understanding of this island. 

The connections between the ancient past and the present are apparent all over Sicily, most clearly in the ancient Roman and Greek ruins that dot the landscape, sometimes in a city center, and sometimes in the middle of an otherwise vast, open landscape, like the Valley of the Temples. And from the ancient times to present, Sicilian stories are often tied to themes of travel, discovery and rediscovery, magic, and heightened emotions. From the strangely tragicomic character of Alcestis in the ancient Greek play by Euripides, to the fake deaths of Shakespeare’s Sicilian plays, to the sweeping drama of Lampedusa’s great 20th-century Sicilian novel The Leopard, this island lends itself to stories of confusion, emotions, and worlds-turned-upside down. In our Literary Sicily program, we’ll investigate why. 

Our 4-week course will start with an overview of Sicily’s literary history and do a deep dive into a handful of texts. In the 11-day trip that follows, we’ll visit sites that inspired this literary history and experience the things that make Sicily justly famous, not just in literature: food, wine, the beauties of the Mediterranean, and its role as a nexus of global cultures. 

In addition to seeing some of the jewels of Sicily that would belong on any itinerary, you’ll also get exclusive literary experiences we’ve designed with local friends and experts, and see things you won’t get on any other trip to Italy. Alongside our outings and lessons, we’ve built in ample free time for you to sightsee, enjoy the renowned food and wine, and take in other Sicilian sites on your agenda. 

Our adult study abroad programs let you capture all of the exploration, wonder, and romance of a college study abroad program with the comforts and necessities of a luxe adult vacation. Join for a travel experience like no other!

Register now!

Classes

Before our trip, we’ll spend 4 weeks learning what literary Sicily is all about. What is it that makes this island the site of so many stories of wandering, travel, mistaken identity, and even shipwreck? How does Sicily’s history lend itself to these tales of adventure and worlds turned upside-down—and how is it that these ideas are still so central to understanding and experiencing the island?

These questions will be our focus as we dive into some of the most beloved stories in the Western world, focusing on Shakespeare, but also discussing the ancient Greek tales that are central to understanding Sicily’s place in literature, as well as the detective fiction and sprawling political sagas that have come to define Sicily’s modern-day literature.

Course Syllabus

Week 1:
Introduction to Literary Sicily: the Greeks, the Bard, and the modern day

Week 2:
Origins: selections from The Odyssey and Greek drama

Week 3:
Shakespeare: The Winter’s Tale & stories of the sea

Week 4:
Shakespeare’s Much Ado About Nothing & comic Sicily

(subject to change)

Each week we’ll have two 90-minute online seminars. After an introduction to literary Sicily, each week will focus on one primary text, with a second session dedicated to the context, the geographical connections, and shorter, modern literary relations. Optional bonus sessions will cover helpful Italian phrases and other travel tips. All classes will be recorded for anyone who’s unable to attend live.

No matter how much background you have in Shakespeare or any other kind of literature, this class is for you! Whether you’re Shakespeare-curious, agnostic, or even a little intimidated, we’ll walk you through everything you need to know to discover literary Sicily. We’ll even send you all the books you need. Trust us—it’s worth it!

And while we recommend doing the reading in advance (obviously; we’re professors), homework is always optional! We promise you’ll get what you need out of the course no matter how much reading you want to do.

Travel Itinerary

Day 1: Palermo & Milazzo (Thursday, May 20)
Our trip begins with a welcome lunch in Palermo, the capital of Sicily, before a short drive to the tiny peninsula of Milazzo, our home for the next three days. Once we arrive, we’ll enjoy our first aperitivo and on-the-ground lesson on Sicily’s rich literary history.

Day 2: Aeolian Islands (Friday, May 21)
Our first outing is a visit to the Aeolian islands off the north coast of Sicily, where we’ll wander the otherworldly locales that reflect the fictional locations and events of so many of Shakespeare’s plays, including The Tempest, The Winter’s Tale, and Twelfth Night.

Day 3: Mt. Etna (Saturday, May 22)
We’ll spend the day on the slopes of Mt. Etna, taking in the sites of Sicily’s storied volcano and experiencing the wine, food, and other aspects of Sicilian hospitality that are central to The Winter’s Tale and Much Ado About Nothing, not to mention many earlier Greek and Roman texts.

Day 4: Milazzo—Ortigia (Sunday, May 23)
Enjoy a leisurely final breakfast in Milazzo before boarding our private coach for the drive to Ortigia, an island within the larger city of Siracusa, where we’ll stay for three nights. Explore the charming, car-free streets of the isle before meeting for an aperitivo and a discussion of Siracusa’s literary roots.

Day 5: Ortigia (Monday, May 24)
Take time to enjoy the beaches, shopping, and sites of Ortigia before meeting to see a performance of an ancient Greek play at the theater in Siracusa’s stunning archaeological park.

Day 6: Noto (Tuesday, May 25)
Visit one of Sicily’s hidden(-ish) gems, the tiny, Unesco-designated town of Noto, 30 minutes outside Siracusa, renown for its baroque architecture and its blending of ancient and modern—as relevant in the architecture as it is in the region’s literature.

Day 7: Ortigia—Agrigento (Wednesday, May 26)
Say farewell to Ortigia with a last cappuccino before the drive to our final stop in Agrigento. On the way, we’ll visit the beatiful town of Ragusa, another Unesco-designated site where we can see the blurring of the borders between Sicily’s ancient past and complicated present.

Day 8: Valley of the Temples (Thursday, May 27)
We’ll visit the Valley of the Temples, a stunning swath of ancient monuments dotting the landscape outside the city of Agrigento. From the Temple of Juno to the Garden of Kolymbethra, we’ll discover how these sites expose the mythical, ancient beginnings of Sicily and lead to its current status as a site of so much literary magic.

Day 9: Agrigento (Friday, May 28)
Our final outing is a trip to Teatro Andromeda, a beautiful, strange destination in the middle of the central Sicilian hills: a Greek theater painstakingly carved by a local shepherd and artist of the course of several years.

Day 10: Agrigento (Saturday, May 29)
Use your final full day in Sicily to take in any extra sites on your list or simply relax at our gorgeous hotel before our final farewell dinner.

Day 11: Farewell (Sunday, May 30)
Enjoy one last breakfast in Agrigento before we drive back to Palermo and say our goodbyes.

Our itinerary is subject to change based on enrollment, availability, and the like—though we don’t plan on it!

Hotels

We’ll stay in 4-star hotels in three different locations across Sicily, each offering a different, one-of-a-kind experience.

Ortigia: Lumè

We’ll have this gorgeous gem of a hotel on the island of Ortigia, in the city of Siracusa, all to ourselves. The boutique hotel in a converted former family home boasts an ocean view and a roof deck with stunning views of the Mediterranean.

Lumè

Southern Sicily: Mandranova

Nestled in the middle of acres of olive trees, this beautiful hotel is part of a family-run olive farm, which also boasts a top-tier restaurant, cooking classes, and an artist-in-residence—perfect for the last leg of our Sicilian adventure.

Mandranova

Though we don’t expect it to happen, hotels may change depending on trip enrollment and availability. If this happens, we’ll change to a comparable 4-stay hotel in the same region.

Program Costs

Total Program Cost: $7600

($7900 after October 15)

Registration and Payment Details

  • $400 non-refundable deposit due at registration

  • Price reflects double occupancy

    • additional fee for single occupancy; email to inquire

    • If you’d like to inquire about other room configurations or the possibility of room shares, please indicate so on the registration page

  • Register before October 15, 2026 to save $300

  • Pay in installments, or pay your balance in full within 4 weeks of registration to save an additional $150

  • For more details about payment methods and deadlines, see the registration page

Register now!

What’s Included

Trip preparation

  • 2 pre-trip meetings to get to know the rest of the group and help you plan and pack

  • One-on-one consultations and recommendations to help you book your travel and make the most of your free time

  • Detailed guides on travel tips, packing suggestions, selecting travel insurance, and other trip logistics

  • Extensive local recommendation lists covering experiences, food and drink, and shopping

Course

  • 12 hours of interactive seminars before the trip, led by a team of experts (90 minutes, twice a week, from April 19 - May 12)

  • 5 lessons in Italy to connect our in-person activities to our course readings (in addition to the activities led by our local experts)

  • All books and other course materials

  • Bonus lessons on Italian language and optional readings

Travel

  • Accommodations at 4-star hotels

  • All transportation between locations and to/from our excursions

  • Tickets for group trips to museums and other attractions

  • All fees and gratuities for expert-led tours and talks

  • Daily breakfast at our hotels

  • 5 group lunches

  • 5 group aperitivos

  • 4 group dinners

Add-ons (for an additional charge)

  • Airport transfer from Palermo airport (PMO) to our welcome lunch near Palermo’s historical center at the start of the trip

  • Custom-designed excursions for your free time

  • Transfer to Palermo airport (PMO) from our farewell aperitivo in Palermo’s historical center at the end of the trip

  • Accommodations in Palermo before the beginning/after the end of the trip

What’s Not Included

  • Airfare to/from Italy

  • Travel insurance for yourelf: all students must have a minimum of $50,000 in medical, evacuation, and repatriation insurance covering the entire span of the trip. For more details, see the FAQ

  • All lunches and dinners not specifically listed on the detailed itinerary (provided after booking)

  • Costs for any optional activities during your free time

  • Incidentals

Key Details

Literary Sicily is open to students ages 18 and up.
Additionally, the list below outlines activities and skills that will be essential for students to do to participate in the program safely and successfully. If you need help figuring out any of these, just let us know—we’re here to help!

For the trip:

  • Walk continuously for 15 minutes at a moderate pace, including navigating some stairs, for ~60 minutes per day—not including any walking you do during your free time.

    • This includes carrying your day bag with anything you want to bring on a given excursion—water, a sweater, etc.

    • As a rule of thumb, if a destination is ~10 minutes away on foot, we’ll walk, weather permitting. If it’s further than that, we’ll arrange taxis. For more information, see our FAQ.

  • Board a high-speed ferry for a ~60-minute journey (one way)

  • Receive and make/send phone calls and WhatsApp messages abroad.

  • Navigate our cities on your own, so you can plan and enjoy your free time.

    • An online map application (such as Apple Maps or Google Maps) is an essential tool for this; we’ll also introduce you to some Italy-specific apps that might be useful for your own adventures.

    • You don’t need to be able to speak Italian to get around our cities, but we’ll give you some language basics anyway!

For the course:

  • Access documents shared via email and/or Google drive.

  • Join and participate in a Zoom meeting.

Sicily Photo Gallery

  • The beautiful baroque city of Ragusa

  • Valley of the Temples, near Agrigento

  • The Greek theater in Siracusa

  • Santa Rosalia, patron saint of Sicilty, in Palermo

    Santa Rosalia, patron saint of Sicilty, in Palermo

  • Teatro Andromeda, a beautiful Greek theater in central Sicily created by a shepherd/artist

    Teatro Andromeda, a beautiful Greek theater in central Sicily created by a shepherd/artist

  • Effortless beauty at an agriturismo near Noto

    Effortless beauty at an agriturismo near Noto

  • Palermo nightscape

    Palermo nightscape

  • view from Ragusa cathedral

    Vista from Ragusa cathedral

  • Cloisters in the town of Monreale, just outside Palermo

    Cloisters in the town of Monreale, just outside Palermo

  • Picture perfect moment in Cefalù

    Picture perfect moment in Cefalù

  • Villa Nettuno

    Villa Nettuno, in an alley in Taormina

  • Charming alley in Ortigia, in Siracusa

    Charming alley in Ortigia, in Siracusa

  • Everyday beauty at an agriturismo outside Noto

    Everyday beauty at an agriturismo outside Noto

  • "Proceed via dance steps"

    "Proceed via dance steps"

  • kitten outside agriturismo

    All worthy agriturismos have at least one adorable kitten

  • Fountain of Diana in Ortigia

    The Fountain of Diana in Ortigia, Siracusa

  • The baroque city of Modica, a Unesco heritage site

    The baroque city of Modica, a Unesco heritage site

  • Morning beauty in Ortigia, Siracusa

  • Ragusa

    Ragusa

  • One of many tiny beaches in Ortigia, Siracusa

    One of many tiny beaches in Ortigia, Siracusa