Day by Day Itinerary

Travel on this exciting Mediterranean vacation in Sicily, with its idyllic climate, dramatic vistas, and hearty cuisine that embodies all things Italian. But Sicily is also rich with its own culture, which is distinct from that of mainland Italy. You'll explore some of Sicily’s most enticing regions—in the vibrant capital city of Palermo, you’ll uncover Sicily’s Arab, Norman, and Roman heritage amid a rich tapestry of Mediterranean cultures. You’ll also enjoy two nights in lovely Agrigento, where you’ll discover the Valley of the Temples, one of the world’s largest and best-preserved sites of Greek ruins, on an included tour. Next, discover the ancient city of Siracusa, known for its rich history of ancient civilizations. Then discover the cliffside resort town of Taormina, where you'll marvel at sweeping ocean and mountain views, presided over by the mighty Mount Etna. Your vacation concludes with two nights in Rome, including a tour of the city's highlights. When you join our newest Grand Circle Land Tour it's all yours, at an incredible value.

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    Depart today on your flight to Palermo, Sicily.

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    Arrival times vary throughout the day, depending on your city of departure. You'll be met at the airport and assisted to your hotel to begin your Mediterranean vacation. This evening, join your fellow travelers, including those who took our Amalfi Coast, Italy pre-trip extension, and Program Director for an orientation walk followed by a Welcome Drink and light dinner at a local restaurant.

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    Begin your morning of discoveries in Monreale, where you'll enjoy a guided tour of the Monreale Cathedral, also known as the Duomo, renowned for its the Arab-Norman splendor. Then return to Palermo to get acquainted with Sicily's capital during a mid-morning panoramic tour, taking in notable sights including its namesake cathedral. You'll also visit the Santa Cita Oratory, a small chapel built in the 16th century as a gesture of thanks to the Virgin of the Rosary for success in the 1571 Battle of Lepanto. Be sure to keep an eye out for the intricate stucco sculpting on the interior walls that depicts the victorious battle.

    Enjoy lunch on your own, and the afternoon to spend as you please. This evening, partake an exclusive Discovery Series Italian With & Without Words language lesson, and then head to a local restaurant for your Welcome Dinner.

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    You have a full day to relax or explore at your own pace. You could visit the Archaeological Museum, featuring a noteworthy Etruscan collection and artifacts from the Hellenic temples at Selinunte. Tour the Abatellis Palace, admiring its gallery of Renaissance paintings. Visit the Mercato delle Pulci, a flea market well known for its antiques. Or take a stroll through the shopping area.

    Or, set off for an optional excursion to Cefalu, an enchanting fishing village and summertime resort sits on a rocky outcrop in the center of Sicily's northern coast. A perfect town for strolling, Cefalu is close to beaches and the blue waters of the Tyrrhenian Sea. The Greeks thought the rocky outcrop, the Rocca, resembled a head—kephalos in Greek—thus, the name of the town. Cefalu lies in a scenic locale between the massive peak and a long, sweeping beach. Against this backdrop rise the lofty twin towers of the cathedral built by Roger II in 1130. This splendid cathedral is one of the finest examples of Arab-Norman architecture and contains luminous mosaics.

    Enjoy dinner on your own this evening.

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    This morning, set out through the Sicilian countryside on your way to the historic hilltop town of Corleone, inspiration for The Godfather book and films.

    You'll enjoy a walk through the town, followed by a chance to learn about Corleone's Past & Present during an informative discussion headed by some of the region's younger residents. Then, enjoy a true Sicilian lunch at a local restaurant.

    This afternoon, you'll arrive at your hotel in Agrigento with time to relax and explore the neighborhood. This evening, dinner is at a local restaurant.

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    After breakfast at your hotel this morning, you’ll visit the extraordinary Valley of the Temples, a UNESCO World Heritage Site, on an included tour. These are among the greatest Greek ruins in the world, and the splendor of the temples—seven in the Doric style, built during the fifth and sixth centuries BC—rivals those in Athens. Here you’ll see the Temple of Juno, with its excellent views of the entire valley, and the Temple of Concordia, beautifully preserved. The oldest ruin is traditionally named the Temple of Hercules, which includes the remnant of a large altar.

    This afternoon, you’ll have free time to explore Agrigento. Later, enjoy dinner at a local restaurant.

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    This morning, you'll enjoy a very special experience—the chance to meet Sicilian schoolchildren at the Istituto Comprensivo M. L. King in Caltanissetta, part of Grand Circle Foundation's World Classroom project. An elementary school with 400 students, M.L. King is working to ensure that Sicily's children get a quality education—no small concern, given that Sicilian students are many times more likely than those of mainland Italy to drop out before graduating high school.

    En route to Siracusa today, you’ll enjoy an agriturismo farmhouse lunch in the countryside nearby the town of Caltanissetta. You’re sure to savor this special lunch served at the Messana family farm.

    Arrive at your hotel in Siracusa in the late afternoon. You’ll have time to relax and reflect on your day’s discoveries before an orientation walk and dinner on your own.

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    This morning you’ll enjoy a guided tour of Ortygia, the historical gem of Siracusa. We will admire the architectural splendor of ancient medieval streets, Baroque structures, and the cathedral—which was fashioned out of an ancient Greek temple.

    Of all the Greek cities of antiquity that flourished outside of Greece, Siracusa was the most important in all of the Mediterranean, and a formidable seafaring power nearly equal to Athens. In the heyday of its power, it dared to take on both Carthage and Rome. At one time, its wealth and size were unmatched by any other city in the ancient world, and today it is one of the richest historical sites in Europe.

    It is said that Siracusa is the birthplace of comedy in Greek theater, and was the only school of classical drama outside of Athens. During your free time you can visit remarkable Greek and Roman ruins, including the cave called "the Ear of Dionysius," because of its unusual shape, resembling a human ear. The cave is more than 200 feet long, and has such good acoustics that the ripping of paper can sound like a gunshot. It is said that the tyrant Dionysius forced his prisoners into the cave at night and was able to hear every word they said.

    After lunch on your own, the rest of the afternoon is at leisure to make your own discoveries. Dinner is at a local restaurant this evening.

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    Enjoy the day exploring Siracusa on your own. Perhaps you'll visit the Temple of Apollo, the oldest known Doric temple in western Europe, or the legendary Fountain of Arethusa. Maybe you'll take the day to stroll and see where your discoveries take you.

    Or discover the Baroque Heritage of Sicily on a full-day optional excursion. where you'll witness some of the best examples of the Sicilian Baroque in Val di Noto (southeast Sicily)—part of a UNESCO World Heritage Site. Your day begins with a visit to the Ragusa Ibla (Ancient Ragusa), where you'll tour the majestic Church of Saint George. This afternoon, your journey continues in the city of Modica, where you'll entice your taste buds with local chocolates during a tasting. The price of this tour includes lunch.

    Dinner is on your own this evening.

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    After breakfast, depart for Taormina. On the way, you’ll visit the small village of Savoca. This sleepy town of 1,700 hugs lush hillsides. Here, many of the scenes of the movie The Godfather were shot, including the marriage of Michael Corleone and Appolonia Vitelli. Enjoy lunch on your own, and free time to further explore.

    Later this afternoon, you’ll check into your hotel and have some free time to relax. Afterwards, enjoy dinner in a local restaurant.

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    This morning, you'll embark upon a walking tour of Taormina, Sicily's most famous resort. Dating from the third and fourth centuries BC, Taormina is perched dramatically high on a rocky promontory overlooking the Ionian Sea. It's a charming medieval town with typical cobblestone streets leading into spacious squares graced by lovely 15th-century palazzi.

    Your tour includes a visit to the extraordinary classical Greco-Roman theater. This is Taormina's most-visited site, offering a view of rare beauty: Mount Etna and the seacoast. In the third century BC, the Greeks carved this theater on the slopes of Mount Tauro out of rock, and even today, the superb acoustics of the theater allow listeners in the last rows to hear a whisper on stage.

    Enjoy an afternoon to explore on your own, perhaps taking the local funivia (cable car) up the hill for a view of the sea. Early this evening, gather for a lecture about the World War II Allied landing in Sicily during the 1943 "Husky" mission. An important moment during the war for Italy, you'll learn about what it meant to the people of Sicily, as well as how the local mafia became involved.

    Enjoy a special Home-Hosted Dinner this dinner, a delightful way to experience everyday life as a Sicilian family welcomes you to share their table for a traditional meal and conversation.

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    The day is yours to peruse your own interests.

    You can also choose to join a full-day optional excursion to gain a new perspective on life at the base of Mount Etna. Visit a luthier in Randazzo to learn about the ancient craft of making and repairing string instruments. Then head to a pistachio farm northwest of the volcano to explore the grounds, learn about this valued product, and enjoy lunch on the grounds. Finally, stop at a local winery on the northern foot for an afternoon tasting.

    Early this evening, partake in a discussion about Italian Volcanoes, including stories about infamous Mount Etna. Dinner is on your own tonight.

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    After breakfast, visit magnificent Mount Etna, Europe's largest active volcano. The peak has changed in size over the years, but is presently listed around 10,000 feet. Etna has been active in modern times, destroying the village of Mascali in 1928, and erupting again in 1971, 1992, 2001, and 2002. It was beneath this mountain that Zeus crushed the multi-headed, hundred-handed, snake-infested dragon Typhoeus, thus attaining dominion over Olympus. Zeus forever banned the dragon to the infernal regions of Tartarus under Mount Etna. The Greeks warned that whenever Typhoeus tried to break out of his confinement, lava would spill forth and earthquakes would crack open the land. Your included tour goes up to the 6,000-foot mark to view evidence of the volcano's activity at Silvestri Crater.

    Enjoy lunch at a local restaurant before returning to your hotel. The rest of the day is yours to spend as you please, and dinner is on your own tonight.

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    This morning, you'll transfer from Taormina to the airport in Catania for our afternoon flight to Rome. On the way, you'll visit a history museum depicting the landing of Allied troops on the southern coast of Sicily in July of 1943. Then, experience a slice of local life when you visit a fish market before lunch on your own.

    Arriving in Rome in the late afternoon, you'll check into your hotel and enjoy dinner on your own.

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    • Meals included:
    • Accommodations:

    After breakfast this morning, you’ll enjoy a panoramic tour of the "Eternal City" that gives you an overview of its main points of interest. You'll see and view the landmarks and monuments that are the signature attractions of this beautiful city.

    Following lunch on your own, enjoy the afternoon at leisure to make your own discoveries. You might stroll along Via del Corso, an almost mile-long stretch of palaces and shops, or spend time in the beautiful gardens of the Villa Borghese. Or stroll the Campo dei Fiori and explore the piazza with its booksellers, inns, small shops, and colorful morning markets.

    This evening, join your fellow travelers this evening for a Farewell Dinner at a local restaurant.

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    • Meals included:

    This morning, transfer to the Rome airport for your flight home. You'll be given a box breakfast to take with you. Or, extend your Mediterranean vacation with our optional post-trip extension to Malta.


Traveler Reviews

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Questions and Answers

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Questions and Answers

Want to know more about one of our vacations? Now, when you post a question, travelers who have been on that trip can provide you with an honest, unbiased answer based on their experience—providing you with a true insider’s perspective.

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Weather & Regional

Before you travel, we encourage you to learn about the region of the world you'll discover on this trip. From weather and currency information to details on population, geography, and local history, you'll find a comprehensive introduction to your destinations below.

Visit our “What to Know” page to find information about the level of activity to expect, vaccination information resources, and visa requirements specific to this vacation.

Currency Cheat Sheet: Submit

What to Know

For more detailed information about this trip, download our Travel Handbook below. This document covers a wide range of information on specific areas of your trip, from passport, visa, and medical requirements; to the currencies of the countries you’ll visit and the types of electrical outlets you’ll encounter. This handbook is written expressly for this itinerary. For your convenience, we've highlighted our travelers' most common areas of interest on this page.

Download the Travel Handbook

What to Expect


  • 5 locations in 15 days

Physical Requirements

  • Not accessible for travelers using wheelchairs or scooters
  • Travelers using walkers, crutches, or other mobility aids must travel with a companion who can assist them throughout the trip
  • You must be able to walk 2-3 miles unassisted and participate in 3-5 hours of physical activities each day, including stairs


  • Daytime temperatures range from 50-92°F during touring season
  • Temperature on excursion to Mount Etna (altitude: 11,000 feet) range from 32-85°F
  • June-August are the warmest months
  • March and December weather can be unpredictable and change quickly within a short period of time


  • Travel over uneven walking surfaces, unpaved paths, steep hills, stairs, and cobblestone


  • Travel by 45-passenger coach


  • Meals will be based on the local cuisine

Travel Documents


Your passport should meet these requirements for this itinerary

  • It should be valid for at least 6 months after your scheduled return to the U.S.
  • It should have the recommended number of blank pages (refer to the handbook for details).
  • The blank pages must be labeled “Visas” at the top. Pages labeled “Amendments and Endorsements” are not acceptable.


U.S. citizens do not need a visa for this trip.

If you are not a U.S. citizen, do not travel with a U.S. passport, or will be traveling independently before/after this trip, then your entry requirements may be different. Please check with the appropriate embassy or a visa servicing company. To contact our recommended visa servicing company, PVS International, call toll-free at 1-800-556-9990.

Vaccinations Information

For a detailed and up-to-date list of vaccinations that are recommended for this trip, please visit the CDC’s “Traveler’s Health” website. You can also refer to the handbook for details.

Before Your Trip

Before you leave on your vacation, there are at least four health-related things you should do. Please check the handbook for specifics, but for now, here’s the short list:

Step 1: Check with the CDC for their recommendations for the countries you’ll be visiting.
Step 2: Have a medical checkup with your doctor.
Step 3: Pick up any necessary medications, both prescription and over-the-counter.
Step 4: Have a dental and/or eye checkup. (Recommended, but less important than steps 1-3.)

What to Bring

In an effort to help you bring less, we have included checklists within the handbook, which have been compiled from suggestions by Program Directors and former travelers. The lists are only jumping-off points—they offer recommendations based on experience, but not requirements. You might also want to refer to the climate charts in the handbook or online weather forecasts before you pack. Refer to the handbook for details.

Insider Tips


Main Trip

  • Grand Hotel Wagner

    Palermo, Italy | Rating: Superior First Class

    The Grand Hotel Wagner is located in the heart of Palermo, and includes a health club and currency exchange. Each room comes with air conditioning, an in-room safe, satellite TV, and daily maid service. High-speed Internet access is available for an additional fee.

  • Dioscuri Bay Palace

    Agrigento, Sicily | Rating: First Class

    Set along the seafront of the San Leone, the Dioscuri Bay Palace is just a few minutes' drive from the Valley of Temples and the Agrigento city center. The hotel features lush gardens, an outdoor swimming pool, and bar. Each room includes satellite TV, safe, minibar, and hair dryer.

  • Grand Hotel Ortigia

    Siracusa, Italy | Rating: First Class

    With views overlooking the scenic Siracusa Harbor, the Grand Hotel Ortigia offers the best of the city's outdoor attractions, as well as indoor and outdoor pools and a health spa. Air-conditioned rooms come with a refrigerator, satellite TV, a telephone, minibar, and daily maid service.

  • Grand Hotel Atlantis Bay

    Taormina, Italy

    Set on the Bay of Mermaids, the Grand Hotel Atlantis Bay features easy access to Old Town of Taormina via cable car just a brief walk away. The 83 rooms all feature private bath with shower, satellite TV, Internet access, and in-room safe. Hotel amenities included an outdoor swimming pool overlooking the bay, a cocktail bar and restaurant featuring live music, and a fitness room.

  • Hotel Albani

    Rome, Italy | Rating: Superior First Class

    Conveniently located near the Villa Borghese and shopping district of Piazza Fiume, the Superior First-Class Hotel Albani gives you easy access to many of Rome’s attractions. Hotel facilities include a restaurant, bar, and currency exchange, and each air-conditioned room features a telephone, cable TV, minibar, refrigerator, safe, and private bath with hair dryer.


  • Grand Hotel Cesare Augusto

    Sorrento, Italy

    The First Class Grand Hotel Cesare Augusto is centrally located near the main square of Sorrento’s Piazza Tasso and shopping area, and five minutes away from public transportation, with many restaurants within walking distance. The hotel includes a restaurant, lounge, roof garden with outdoor swimming pool (open from June to September), and solarium, and each room features a private balcony, air-conditioning, telephone, TV, safe, and private bath with hair dryer.

    Please note: Select departures feature similar accommodations.

  • The Victoria Hotel

    Sliema, Malta | Rating: Superior First Class

    The Superior First-Class Victoria Hotel is a small hotel with a Victorian flair. Each of its 140 air-conditioned rooms boasts a private bath, satellite/cable TV, minibar, telephone, and coffee- and tea-making facilities. The hotel's city center location makes it ideally located for discovery, while its indoor/outdoor pools and two restaurants make for a relaxing stay.

Flight Information

Your Flight Options

Whether you choose to take just a base trip or add an optional pre- and post-trip extension, you have many options when it comes to personalizing your air—and creating the Grand Circle vacation that’s right for you:

Purchase Flights with Grand Circle

  • Work with our expert Air Travel Consultants to select the airline and routing you prefer
  • Upgrade to business or premium economy class
  • Customize your trip by staying overnight in a connecting city, arriving at your destination a few days early, or spending additional time in a nearby city on your own
  • Combine your choice of Grand Circle vacations to maximize your value

Make Your Own Arrangements

  • Make your own international flight arrangements directly with the airline
  • Purchase optional airport transfers to and from your hotel
  • Extend your Land Tour-only Travel Protection Plan coverage and protect the air arrangements you make on your own—including your frequent flyer miles

OR, leave your air routing up to us and your airfare (as well as airport transfers) will be included in your final trip cost.

Estimated Flight Times

We understand that international travel has unique challenges including fewer airline choices and limited flight schedules. The chart below provides estimated travel times and the typical number of connections from popular departure cities to help you plan for your trip.

Please note that traveling to Palermo, and from Rome, will require multiple connections, and these flight rigors should be taken into consideration.

Partner since: 2013
Total donated: $167,728

Preparing Sicily's children with modern technology

Just by traveling with us, you’re supporting Grand Circle Foundation’s World Classroom initiative and helping Sicilians schoolchildren prepare for their future. Because the best way to sustain a community is through education, we’ve donated funds to the Istituto Comprensivo M. L. King. You’ll visit this school (when in session) and see the energy of the students who will write the next chapters in Sicily's long history.

Istituto Comprensivo M.L. King

Partner since: 2013 • Total donated: $2,496

When you travel to Sicily with Grand Circle, you'll be supporting the technological futures of some of its schoolchildren. Grand Circle Foundation has been working with the Istituto Comprensivo M. L. King to ensure that its 400 students have access to books as well as a computer, printer, video projector, and more. Though Sicily has historically lagged behind mainland Italy in school completion rates, the educators here are optimistic that by providing an education with modern technology, these children can provide a bright future for their island.

School in session:

September through early June

Gifts to bring if you're visiting:

  • Pencils
  • Early reader books
  • Educational toys
Alan and Harriet Lewis founded Grand Circle Foundation in 1992 as a means of giving back to the world we travel. Because they donate an annually determined amount of revenue from our trips, we consider each one of our travelers as a partner in the Foundation’s work around the world. To date, the Foundation has pledged or donated more than $97 million in support of 300 different organizations—including 60 villages and nearly 100 schools that lie in the paths of our journeys.

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What Makes This Trip Unique

Exclusive Discovery Series Events

  • Italian With & Without Words discussion. Learn how to parla italiano and connect with locals during an exclusive Discovery Series Italian lesson on your tour.
  • Corleone’s Past & Present discussion. Learn about the history of the Mafia from a village native.
  • Agriturismo farmhouse lunch. Share Sicilian cuisine and hospitality as you join a family at their country house.
  • World War II lecture. Learn about the 1943 landing of Allied troops in Sicily and mafia involvement during the "Husky" mission.
  • Home-Hosted Dinner. Join a local family for a traditional meal and a look inside local life on the island.
  • Italian Volcanoes discussion. Learn what it’s like having Mount Etna as a neighbor.

Enjoy the opportunity to visit 2 UNESCO World Heritage Sites

  • Siracusa
  • Valley of the Temples in Agrigento

10 Reasons to experience Discover Sicily: Heart of the Mediterranean—in the words of our travelers

We often find that the best endorsements of our discovery-rich vacations come directly from our travelers. Stunning architectural achievements, breathtaking Italian landscapes, and succulent Mediterranean cuisine await those who travel to Sicily with us. Here are some memorable experiences our travelers shared.

Agrigento, Sicily
"Agrigento, with its 'Valley of the Temples,' was as interesting and awe-inspiring as Athens. Grand Circle went out of their way to provide a view of the temples at night, including a hillside stop for a toast of limoncello. We also visited an archeological museum which was superb."
A 6-time traveler from Annadale, VA

Local people
"Francesca (the Program Director) would stop residents on the street and engage them in conversation which she would translate for us. We went into people's homes to see what it was like to live as a Sicilian. We broke bread with locals and learned about their daily struggles and hopes. Of course we had the usual array of local professional guides who were knowledgeable and eager to share their experiences and information, but for me, the interactions with the man or woman on the street were more memorable."
A 4-time traveler from Winter Haven, FL

Malta post-trip extension
"I chose to do the Malta extension really not knowing what to expect. Well, it was a wow! Limestone buildings that were Arabic styled, with arches and balconies; driving on the left; and English pubs intermingled with Maltese specialties and all the fish I could want! It's easy to get around the islands via local buses and ferries ..."
A 10-time traveler from Strasburg, PA

Local history
"The Greeks made a good decision when they decided to settle Sicily. Of course they were not the only occupiers. The Norman, Greeks, Spanish, and Moors all left their fingerprints on this marvelous island. The history and the ancient ruins are a feast for the eyes ... We really enjoyed our history lesson and look forward to traveling with Grand Circle again in the future."
A 2-time traveler from Harwich, MA

Home-Hosted Lunch
"I would say that the Home-Hosted Lunch was not only an extremely memorable moment of this trip, but the best Home-Hosted meal we have had. It was a culinary and social experience!"
A 4-time traveler from West Orange, NJ

Cefalu optional tour
"Cefalu was a surprise. A lovely city on the sea. The Duomo was like an art gallery, our luncheon was great, and we had sufficient time to explore the town."
A 12-time traveler from Atlanta, GA

Savoca, Sicily
"A magical moment was in Savoca, where part of the Godfather movie was filmed. Near the end of our tour it started raining, and at noon this lovely church played Ave Maria in this gorgeous setting, everyone ran to the bus, but two of us stood in the rain and listened with tears streaming down our faces ... It was a moment that I will always remember."
A 5-time traveler from Benson, AZ

Local cuisine
"Food wise, we have many highlights ... The Italian word for watermelon is anguria. We saw anguria granita at an ice cream shop in front of Cefalu's cathedral ... Also, give brioche a try—two scoops of ice cream sandwiched in a sweet bun. It was 2 euro per brioche everywhere, and you get to choose 2 flavors of ice cream to put in your brioche ... While in Taormina, we passed by a restaurant called La Grotta Azzurra with seafood packed in ice displayed in a glass case. We saw sardines, so we inquired if they could make fried sardine. Yes ... the fried sardine was so crispy and tasty that we rated it one of the best seafoods we had in Sicily."
A 4-time traveler from Reading, MA

Mount Etna
"Standing in a crater on Mount Etna was amazing, just sorry we missed a small eruption by a week."
A 6-time traveler from Mount Etna

Amalfi Coast, Italy pre-trip extension
"You can't find anything more beautiful than the journey along the Amalfi Coast and stops in Amalfi and Positano. Truly a joy."
A 16-time traveler from Seven Hills, OH

Want to travel to Sicily? Call us toll-free at 1-800-221-2610 for reservations and information.


The city of antiquity

by Philip McCluskey for Grand Circle

Cicero called Siracusa “the greatest Greek city and the most beautiful of them all.”

Cicero called Siracusa “the greatest Greek city and the most beautiful of them all.” Archimedes had his famous “Eureka!” moment here, and luminaries such as Plato, Sappho, and Caravaggio were drawn here during the city’s artistic and intellectual awakening. The city is mentioned in the Bible as a stop for the proselytizing Saint Paul, and is the celebrated birthplace of Greek theater. Siracusa has many claims to fame, and its history is as fascinating as it is long.

From colony to colonizer

Siracusa was originally settled by the Corinthians in 734 BC, and the settlers chose an ideal location on the southeastern coast of Sicily: It had two natural ports, was near fertile lands, and could be easily defended from attackers. Within 100 years, the city had become so successful that it was sending out colonists to other parts of Sicily. It soon became a locus of power on the island: a status that drew those in search of power themselves.

Dionysius the despot

The city reached its peak during the tyrannical reign of Dionysius the Elder, who ruled from 405 until 367 BC. Rising from humble beginnings as a clerk in public office, Dionysius used his impressive military prowess (and considerable guile) to become ruler of the city. His rule saw a number of wars—most notably with Carthage—yet it also saw the development of the city walls and its reputation as a strong military power. One site in Siracusa is named for the famous tyrant: the Orecchio di Dionisio, or “Ear of Dionysius.” The entrance to this 200-foot-long cave is similar in shape to a human ear, which may help explain the cave’s remarkable acoustics. Any sound made inside the cave can be amplified up to 16 times; it is said that the eponymous dictator would cast his prisoners here at night so that he could hear every word they said.

A stream of conquerors and a string of bad luck

After the Romans took over in AD 211, Siracusa retained its status as a provincial capital but gradually started to lose its power and influence. Subsequent periods of Frankish, Norman, Byzantine, Arab, Swabian, and Spanish rule only further depleted its standing in the Mediterranean. Earthquakes in 1542 and 1693 destroyed a number of important buildings. By the time it was being bombed by both Allied and German forces during World War II, much of the city’s rich cultural heritage had been destroyed or was in disrepair.

Restoring Siracusa

Thanks to impressive reconstruction efforts undertaken in Siracusa, some of the most interesting pieces of the city’s history have been restored. The most important reemergence has been the island of Ortygia, the nucleus of the city. Strolling through the medieval streets here, travelers see the remnants of Greek, Roman, Norman and Baroque architecture, recalling the many iterations of life on this tiny isle. They are all clustered around the Piazza de Duomo, the attractive city square that is home to the city’s famous Cathedral.

You can also find the Fountain of Arethusa in Ortygia, a site which is featured in Greek mythology. It is said that the river god Alpheios fell in love with a water nymph named Arethusa. Arethusa, the story goes, ran all the way to Ortygia to escape the river god’s advances. When she arrived, she asked for the help of the goddess Artemis, who protected all women. In order to hide Arethusa from the pursuing Alpheios, Artemis turned her into a freshwater spring. Alpheios was clever however, and rerouted his river to mix with Arethusa’s. Now, it is said that Arethusa and Alpheios mingle forever in this fountain.

Siracusa is also said to be the birthplace of Greek theater, and was the only school of classical drama outside of Athens. The Greek Theater, originally built in the fifth century BC, was carved from rock on Temenite Hill and was home to performances of legendary playwrights Sophocles, Euripides, and Aeschylus. Though it certainly shows signs of age (and you would too if you were 2,600 years old), the theater is remarkably intact—so much so that it is still a center of public life of the city. In fact, Siracusans still gather here for Greek tragedies, especially in May and June for the city’s annual Greek Theater Festival.

A fascinating past, a bright future

In naming Siracusa a World Heritage Site in 2005, UNESCO noted that the city offered “a unique testimony to the development of Mediterranean civilization over three millennia.” The city is now among the most popular places to visit in Sicily, thanks in large part to the edificial evidence of its rich and varied history. Perhaps it is fitting that Siracusa’s past is a big part of what will no doubt be a promising future.