Italy: Sicily

Guided Walking Tour, Italy: SicilyGuided Walking Tour, Italy: Sicily

Italy

Sicily

overview

Is Sicily the soul of Italy? You decide, on this journey into the island’s tumultuous past and glorious present, as you become one of the travelers Sicily has captivated for centuries. Your immersion in ancient splendor begins on arrival in Syracuse, amidst Greek and Roman wonders and Baroque piazzas. A naturalist’s paradise, Sicily is renowned for birding hot spots like coastal Oasi Naturale di Vendicari; legendary Mt. Etna, Europe’s largest active volcano; and 4,000-year-old tombs among the limestone formations at the Necropolis of Pantalica. In town, shop the delightful market, then head into the countryside to explore castles and sprawling villas with vast art collections, rural villages and vineyards…and unspoiled nature preserves filled with rare plants and wildlife. From the olive groves of Castelbuono and ancient t emples in Cefalù, to the cultural riches of Selinunte Archaeological Park and spectacular views in hill towns like Erice, you’ll glory in Sicily’s grand pageant of history and scenery.

 

 

Activity Level
Moderate
with some
easy days;
4-8 miles daily
Meet
Syracuse (Siracusa), Sicily
Depart
Palermo, Italy
Daily Itinerary
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itinerary
Reading List
Recommended
pre-trip reading
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From our blog

Guided Walking 
10 days, 9 nights Trip Includes 

Trip Includes

  • Two expert, local guides (for groups of 8 or more), with you 24/7
  • All meals except for two dinners; local wine included
  • All accommodations while on tour
  • Transportation from the meeting to the departure point
  • Entrance fees and special events as noted in the itinerary
  • Basic travel insurance coverage
  • The unbeatable and cumulative experience of the CW staff
per person double occupancy
Solo surcharge + $0
 

2014 Single supplement + $675
2015 Single supplement + $695
Call 800.234.6900 to book this trip.

REQUEST RESERVATION
Number of Travelers
Total in your party
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per person double occupancy

Call 800.234.6900 to book this trip.

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Itinerary and Accommodations

Days
Destination
1
Syracuse
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2
Syracuse
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3
Syracuse
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4
Caltagirone
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5
Castelbuono
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6
Castelbuono
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7
Erice
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8
Menfi
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9
Menfi
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10
Menfi
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Day 1

Syracuse

Arrival in Syracuse. Syracuse Archaeological Park and historical walking tour of Ortygia; 3 hours, easy

Your exploration of Sicily starts in and around the atmospheric city of Syracuse. At one time rivaling Athens as the most important and powerful city of the ancient world of Greater Greece, known as Magna Graecia, modern-day Syracuse is a UNESCO World Heritage site and the cultural and administrative capital of southeastern Sicily—an area known for its extravagant Baroque architecture, historical ruins, gastronomic delights, beautiful landscapes, and beaches. The city is divided into “mainland” Syracuse and the islet of Ortygia—its historical heart and your home for three nights—connected by the Ponte Umbertino bridge.

Your tour begins with a short drive to the edge of the city and the Parco Archeologico della Neapolis. Syracuse’s Archaeological Park is a treasure trove of important Greek and Roman monuments. Your first stop is the spectacular 5th-century B.C. Greek Theater, one of the finest and largest of its kind, still hosting Greek plays in the summer months. Nearby is the 2nd-century Anfiteatro Romano, the largest Roman amphitheater in Sicily and third-largest in Italy after the Colosseum in Rome and the amphitheater in Verona. Unlike the Greek Theater, the Roman Amphitheater bore witness to more gruesome events, such as gladiator fights and slave punishments.

By late afternoon you return to Ortygia for a guided walking tour, starting at the remains of the Temple of Apollo—a perfect example of Sicily’s multi-layered history. This 6th-century B.C. Doric structure became a church in Byzantine times and a mosque under Arab rule. You move on to gold-tinted palaces, campanili (bell towers), and church domes. Narrow, cobblestoned lanes open up to the irregularly shaped Piazza del Duomo, acclaimed as one of Italy’s most beautiful squares. At one time the acropolis of ancient Greek Syracuse, this elegant piazza is ringed by exquisite Baroque buildings, constructed after the 1693 earthquake. Its centerpiece is the Duomo (cathedral), the city’s best example of the successions of evolving architectural styles that have shaped the city over the centuries. The cathedral’s Baroque façade disguises the 5th-century B.C. temple of Athena; however, 26 of the temple’s Doric columns remain intact and are visible both inside and outside.

You return to your hotel—an elegant 14th-century aristocratic property overlooking a tiny waterfront piazza and the Ionian Sea—before gathering for a welcome aperitivo. Dinner tonight is a short walk away at an inviting trattoria in town.

Hotel Domus Mariae Benessere

A former 14th-century aristocratic property, the elegant Domus Mariae Benessere has been recently refurbished and is spectacularly situated on the island of Ortygia in the historic heart of Syracuse. The hotel features a therapeutic spa and lovely panoramic rooftop terrace overlooking the sea.

Day 2

Syracuse

Oasi Naturale di Vendicari and Noto; 4-7 miles, easy to moderate

Following breakfast, an optional short walk from the hotel takes you to Syracuse’s colorful daily morning market, which sells a dazzling array of fresh fruit and vegetables, local cheeses and herbs, glistening freshly caught fish, and hams and cured meats. After choosing a few snacks for the day or mementos to bring home, you drive one hour to one of the most beautiful spots in southeastern Sicily: the Oasi Naturale di Vendicari, a complex of coastal marshes and a serene sandy beach, which, depending on the season and time of day, provides a protected home for large populations of migratory birds such as ducks, white egrets, black storks, and even European flamingos. Footpaths lead through the salt fields of the Pantano Grande to an abandoned tonnara (tuna factory) and the ruins of a Norman tower known as the Torre di Vendicari. From here, the view embraces the entire reserve, from the splendid isle of Vendicari to Capo Passero in the distance. Depending on the weather, you may be enticed to take a swim! Arriving on foot at a family-owned agriturismo, you enjoy a lunch of regional specialties, including grilled vegetables, local Sicilian provola, pecorino, and tuma cheeses, and freshly made pasta.

Following lunch, a 15-minute drive brings you to Noto, one of Sicily’s most intriguing cities; Sicilian writer Leonardo Sciascia called Noto a “garden of stone, a city of gold, a theatrical city, a Baroque city.” Ancient Noto was destroyed by the 1693 earthquake, and in a demonstration of civic pride, a new town was built a few miles away, in accordance with the period’s most advanced ideas in city planning. Today the “new” Noto is unique for the uniformity of its architecture; most buildings were constructed at the same time, in the same style (by the master of Sicilian Baroque, Rosario Gagliardi), and of the same golden stone. Not surprisingly, the town has recently become a UNESCO World Heritage site. You stroll the narrow alleyways beneath the ornate façades and balconies, palaces, and churches before returning to Syracuse for the evening. There is time to relax before walking to dinner at a charming local restaurant.

Hotel Domus Mariae Benessere

A former 14th-century aristocratic property, the elegant Domus Mariae Benessere has been recently refurbished and is spectacularly situated on the island of Ortygia in the historic heart of Syracuse. The hotel features a therapeutic spa and lovely panoramic rooftop terrace overlooking the sea.

Day 3

Syracuse

Mt. Etna; 6-10 miles, moderate to challenging, 800-2,200-ft. elevation gain and loss

The day begins with a two-hour drive to Mt. Etna, Europe’s largest active volcano, over 11,000 feet high and occupying an area larger than metropolitan New York. The mountain presents a fascinating alpine environment with its combination of nature and the uncontrollable essence of fire. A range of walking routes are weather- and volcano-dependent and may include adventurous climbs to the recently formed craters or around Monte Nero and the Bottoniera, or through the Linguaglossa pine forest, crossing a corridor of hardened lava flow. A simple lunch of Sicilian specialties is provided at the Rifugio Citelli, a mountain refuge situated at 5,712 feet.

In the late afternoon you return to your home in Syracuse for an evening of independent strolling and dining.

Hotel Domus Mariae Benessere

A former 14th-century aristocratic property, the elegant Domus Mariae Benessere has been recently refurbished and is spectacularly situated on the island of Ortygia in the historic heart of Syracuse. The hotel features a therapeutic spa and lovely panoramic rooftop terrace overlooking the sea.

Day 4

Caltagirone

Necropolis of Pantalica; 4-6.5 miles, moderate, 1,000-ft. elevation gain and loss. Transfer to Caltagirone

After an early breakfast buffet of fruit, yogurt, juices, cold cuts, and homemade pastries, you depart for one of Sicily’s most fascinating nature reserves and archaeological sites, the Necropolis of Pantalica. A plateau rising between the canyons of the Anapo and Calcinara Rivers, it was inhabited from prehistoric times to the Middle Ages. The burial grounds carved in its steep rock walls comprise the largest complex of its kind in Sicily, with over 5,000 tombs dating as far back as the second millennium B.C. You walk through a dramatic river-carved landscape of limestone formations, luxuriant in colorful, fragrant Mediterranean vegetation.

Nearing lunchtime, a short transfer delivers you to another traditional Sicilian lunch at a nearby family-owned restaurant and agriturismo. Dishes are derived from locally sourced, seasonal ingredients and reflect the ancient local traditions of the Anapo Valley.

By mid-afternoon, you continue on a two-hour drive to the outskirts of Caltagirone, where you spend one night at a very simple yet beautifully renovated Sicilian stone farmhouse located in the open countryside amidst towering palms, olive trees, and neighboring forest. Following time to settle in to your room or relax by the outdoor pool, a feast of traditional specialties, perfectly paired with local Nero d’Avola red wine, is served in the warm wood-beamed dining room.

Agriturismo Vecchia Masseria

Caltagirone, Italy

A beautifully renovated traditional farm estate set in the midst of fields and forest with swimming pool, Jacuzzi, and pub and restaurant. Please note guest rooms are very simple in style. In addition, there are no telephones in guest rooms.

Day 5

Castelbuono

Mount Ganzaria; 4- or 7-mile options, easy. Visit of Villa Romana del Casale. Transfer to Castelbuono

Awakening to peaceful countryside, after breakfast you have the option of relaxing at your inn and enjoying the facilities (including the Jacuzzi), or setting off on foot to walk to neighboring Mount Ganzaria, with two options of varying distances. The mountain derives its name from the Arabic word for wild boar, yhanzaria, because of boars’ abundance on the mountain in ancient times. This area has been settled from the prehistoric age until the present. Your route includes a Byzantine necropolis and takes you through vegetation of cork oaks, eucalyptus, walnut groves, dwarf fan palms, and orchids, inhabited by foxes, porcupines, and weasels. Broad views on one side look over the Catanian plain and, on the other, toward southern Sicily.

Returning on foot to the masseria for a light lunch, you then take leave of it and drive a few miles away to the magnificent Villa Romana del Casale, considered the most important Roman archaeological site in Sicily. This Roman villa or hunting lodge, now a UNESCO World Heritage site, was built around the 3rd and 4th centuries (A.D.) and is known for its extraordinary collection of mosaics, in various stages of restoration. Walkways take you through some of its 40 rooms that are carpeted with 4,200 square yards of magnificent mosaics depicting vivid scenes from mythology, hunting and fishing, and various aspects of everyday Roman life.

Concluding your visit, an approximately two-hour drive brings you to the beautiful hillsides surrounding Castelbuono, an idyllic town around a 14th-century castle, and to your hotel for the next two nights—a former Benedictine abbey nestled amongst vineyards, olive groves, and cork trees, with wonderful views over the Madonie Mountains and down to the Tyrrhenian Sea.

This evening, there is time to settle in and enjoy the expansive property before dinner in the hotel’s elegant dining room.

Relais Santa Anastasia

Castelbuono, Italy

This former Benedictine abbey overlooking the Madonie Mountains is surrounded by vineyards, olive groves, and cork trees, which can be explored by a trail from the hotel; it features spacious rooms, swimming pool and Jacuzzi, gardens, and fine dining featuring its own farm produce.

Day 6

Castelbuono

Parco Naturale Regionale delle Madonie; 4-8 miles, moderate to challenging

This morning you have another possibility to opt out of the day’s walk and choose instead to relax at the hotel in one of the many beautiful common areas or poolside, or to enjoy a self-guided walk through the vineyards and hills surrounding the Relais (maps provided). Alternatively, join your guides in discovering the lush natural reserve of the Parco Naturale Regionale delle Madonie, the Madonie Mountains regional park, approximately one hour from the hotel. This sanctuary, just inland from the seaside town of Cefalù, encompasses the Madonie mountain range and Sicily’s second-highest peak after Mt. Etna, Pizzo Carbonara at 6,492 feet. A botanical treasure trove, the park contains more than half of the 2,600 known plant species in Sicily. The tranquil habitat also includes charming villages, farms, and vineyards, and in the winter, it is a ski resort, therefore, the area has somewhat of an Alpine appearance, with distinctive chalet architecture. A range of walking options is available in the park depending on the weather and the group’s interest. For lunch, you dine on simple authentic Sicilian fare at a traditional stone mountain refuge.

En route back to the hotel, you stop in the town of Castelbuono for a stroll and visit to its 14th-century Matrice Vecchia (Old Cathedral Church), which is built over the ruins of a pagan temple, with its crypt  beautifully decorated in frescoes illustrating the Passion, Death, and Resurrection of Christ.

Dinner this evening is the fruit of your labor in an optional hands-on cooking class! You join Chef Antonio Bonadonna in the kitchen and help him prepare regional dishes, homemade pasta, and an accompanying sauce, while learning some of the many culinary traditions of the region, which are essentially based on simple fresh ingredients. Simplicity...the Sicilian way.

Relais Santa Anastasia

Castelbuono, Italy

This former Benedictine abbey overlooking the Madonie Mountains is surrounded by vineyards, olive groves, and cork trees, which can be explored by a trail from the hotel; it features spacious rooms, swimming pool and Jacuzzi, gardens, and fine dining featuring its own farm produce.

Day 7

Erice

Walking tour of Cefalù; 1 hour, easy. Segesta; 1 mile, easy. Transfer to Erice. Walking tour of Erice; 1 hour, easy

Today is a transfer day with a final destination of Erice. The day begins with a visit of medieval Cefalù—a beachside resort on the Tyrrhenian coast. You ease into your day’s adventure by strolling the town’s well-preserved streets and visiting its historical sites. Following a guided visit to the town’s magnificent Norman-era cathedral, there is time for a little independent exploration: shop for local ceramics, stroll the beach, or visit the town’s tiny museum, whose most famous work is the “Portrait of an Unknown Man” by Antonello da Messina, one of the most famous European painters of the 15th century.

You depart Cefalù by late morning, driving two hours to Segesta. Following a Sicilian farmhouse lunch, you proceed to Segesta’s marvelous Doric temple. Dating to 430 B.C. and situated alone in a field, this is one of Italy’s best-preserved ancient temples. Founded by the Elymians, a mysterious ancient people, the city of Segesta was fought over for centuries before eventually being conquered by the Romans.

From Segesta, an additional hour’s transfer brings you to one of Italy’s most spectacular hill towns: Erice, set atop the legendary Mt. Eryx at 2,460 feet. On a clear day, there are panoramic views across the plains of Trapani, down the west coast of Sicily, and even to Cape Bon in Tunisia. Originally settled by the ancient Elymians, the town boasts a fascinating history and is an important historical site associated with fertility goddesses—the Carthaginians’ Astarte, Greeks’ Aphrodite, and Romans’ Venus. Arriving through a maze of medieval streets, tiny piazzas, churches, and Baroque flowering balconies to Erice’s enchanting historical core, you set off on an afternoon walking tour of the medieval town and some of its important sites: the hilltop Norman Castello di Venere (Castle of Venus), which offers spectacular views, and the 14th-century main town church of Chiesa Madre and bell tower, constructed from stones from the ancient Temple of Venus on the same site. The majestic Norman castle was a massive fortification and the power seat of these 11th-century conquerors in western Sicily.

After you settle into your hotel for the night—a former private palazzo with frescoed ceilings—your guides provide restaurant suggestions for dinner on your own nearby.

Hotel Elimo

Erice, Italy

In the historic center of Erice, a renovated family-owned palazzo offers very simple guest rooms and eclectic common areas with frescoed ceilings and antique furnishings, a wine bar, and interior garden.

Day 8

Menfi

Riserva Naturale di Monte Cofano; 4-8 miles, moderate. Transfer to Menfi

Departing Erice, a 45-minute transfer delivers you to today’s walk in the Riserva Naturale di Monte Cofano, a towering limestone promontory jutting out between the turquoise Gulfs of Bonagia and Cofano. The reserve features well-maintained paths, panoramic sea views, secluded bays and steep cliffs, and diverse flora and fauna. The landmark headland is also home to historic watchtowers, immense caves, and archaeological sites of prehistoric settlement.

Finishing up the walk, a 10-minute drive brings you to lunch featuring western Sicilian cuisine in the neighboring town of Custonaci. Afterward, you transfer just under two hours south to the countryside of Menfi and your home for the next two nights at a vineyard-side resort. The individually decorated guest rooms open onto private terraces with views over herb and flower gardens and vineyards. Following a welcome aperitivo, you proceed to a dinner of superlative cuisine served at a large communal table in the hotel’s dining room, accompanied, of course, by the estate’s renowned vintages.

Planeta Estate - La Foresteria

Menfi, Italy

Set amidst the vineyards of the renowned Planeta winery, a secluded four-star resort features spacious guest rooms with individual terraces, swimming pool and steam bath, walking paths, and exclusive fine dining.

Day 9

Menfi

Selinunte archaeological site; 3-5 miles, easy. Visit to "La Dispensa" winery and vineyards

After breakfast in your tranquil resort, you drive about 30 minutes to Selinunte, an ancient city that is now one of Sicily’s most dramatically sited Greek ruin complexes. This city, whose name is derived from the Greek word for celery, selinus, was one of ancient Greece’s most prosperous colonies as early as the 7th century B.C., and hence the object of centuries of battles.

Following lunch, a leisurely afternoon at the hotel offers time to pack, relax, and perhaps swim in the hotel’s panoramic outdoor swimming pool. This evening a short drive brings you to La Dispensa winery and vineyards, also owned by the Planeta Estate. Planted in nearly 300 acres of vines, the winery produces quality white and red wines including the super cru Cometa and Segreta lines. Following a guided tour of the historic winery, you gather in the library, home to hundreds of books dedicated to the grapevine, for a tasting of Planeta wines paired with breadsticks, crostini, and olives.

A farewell dinner follows on the outdoor terrace (weather permitting), a perfect venue for toasting your discoveries of enchanting Sicily.

Planeta Estate - La Foresteria

Menfi, Italy

Set amidst the vineyards of the renowned Planeta winery, a secluded four-star resort features spacious guest rooms with individual terraces, swimming pool and steam bath, walking paths, and exclusive fine dining.

Day 10

Menfi

Departure from Palermo

After a final relaxed breakfast, you transfer 90 minutes either to the Palermo airport or to the city’s centrally located bus station to make your onward travel connections.

Itinerary Disclaimer

Bear in mind that this is a typical itinerary, and the actual activities, sites, and accommodations may vary due to season, special events, weather, or transportation schedules. We reserve the right to alter the itinerary since tour arrangements are made up to a year in advance, and unforeseen circumstances that mandate change may arise. Itinerary changes are made to improve the tour and your experience. If you are currently booked on a CW adventure, an itinerary has been sent to you for your exact departure date. Please call CW at 800.464.9255 if you have any questions about the exact itinerary or hotels selected for any of our tours.

Guides

Orietta Piazza

With a love of languages and travel, native Sicilian Orietta studied English, German, and Spanish at the University of Catania, graduating with a degree in modern languages. In addition to guiding our walking tours in Sicily and Puglia & Basilicata, Orietta leads tours exploring Sicilian genealogy for many visitors to the island who are of Sicilian heritage. In addition to traveling, she is fond of gardening and plays the guitar.

Loredana Grasso

A native Sicilian, Loredana studied English and art history at the University of Catania. She has worked in translation, led cultural tours for students, guided nature tours, and provided information at an archaeology museum in both English and Spanish. She also guides visitors of Sicilian heritage in exploring their genealogy and family histories. Loredana’s love of the outdoors and her passion for her homeland enhance guests’ experience of Sicily.

Alessandro Gullo

Alex is a native of Italy with Sicilian ancestry. Educated in the U.S. as well as Italy, he is a certified guide of historic monuments in Umbria. He combines his charming personality with a vast knowledge of culture, art, history, food, and wine on many of our vacations in Italy.

Guest Comments

C. Weden, Virginia, October 2013

Overall the trip was excellent, the weather was perfect, the hikes were well planned, the food was spectacular, and last but not least, the guides Orietta and Loredana were alone worth the trip.i

R. Margo, Virginia, May 2013

The sights to see and places to hike were above and beyond ordinary; the guides were so patient, wonderful, and enthusiastic; both of them (Orietta and Alex) love their jobs and this love is passed on to the tour participants. The choice of accommodations also was a highlight: the places that we stayed are pure class. This trip was absolutely magnificent!

S. Mathews, Minnesota, September 2012

It was my first time on a trip like this and I thought it was better than I had imagined. We had an incredible guide in Orietta and our hikes and other activities were very well organized.

J. Malkerson, New Mexico, September 2012

Immersing ourselves into the culture, terrain, and geology of Sicily, gave me a sense of time present and past. Where we walked, there were layers of history...people...creating homes and destinies: mountains giving us views of millions of years past history...and panoramic views of today. The archaeology of time past...the clustering cities of today and castles and villas of yesterday...created a rich tapestry of life.

A. Conrad, Kansas, September 2012

The geological & cultural knowledge of our CW guides greatly enriched our appreciation of the sites we visited and our understanding of the history of the island. Their ability to be flexible & imaginative as logistic challenges arose was superb & allowed us to relax & enjoy our trip.

N. Breitling, Pennsylvania, September 2012

I love meeting new people from other parts of the country and hearing about their travel experiences. I also enjoy going to places I would not ordinarily go myself and of course hiking on trails and not worrying about getting lost! I can't say enough about Loredana and Orietta! They went over and above to give us the flavor of Sicily. 

C. Stearns, Oregon, September 2012

The guides were superb, as were the accommodations and the meals. Overall, the trip exceeded our initial expectations in terms of the places we visited and what we learned about Sicily—current and ancient. We had a unique opportunity to visit ancient sites as well as modern ones. Throughout the guides worked overtime to respond to our special needs and interests, so that each day's agenda actually went well beyond the published itinerary. For example, one day they arranged a stop at a local wine pressing business so we could see how the grapes from mom and pop vineyards were processed. Often the weather (very warm) or acts of nature (local forest fires) forced a change in plans. Our guides were creative and unflappable, and we came to look forward to these small changes as exciting opportunities to see more of the real Sicily.

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