DAY 1

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 historic 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. 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—the 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 welcome feast, perhaps starting with an antipasti of the tiny delicately seasoned clams and a main course of fresh swordfish at an inviting trattoria in town.
Hotel Domus Mariae Benessere, Syracuse

DAY 2

After a breakfast buffet of fruit, yogurt, juices, cold cuts, and homemade pastries, 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 flamingoes. 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!

Nearing lunchtime, a fifteen minute-drive brings you to Noto, one of the 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. Arriving at a lively trattoria in the center of ancient Noto, you enjoy a lunch of regional specialties including grilled vegetables, local Sicilian provola, pecorino, and tuma cheeses, and freshly baked bread.

Following lunch, 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 local restaurant.
Hotel Domus Mariae Benessere, Syracuse

DAY 3

The day begins with a two-hour drive to Mt. Etna, Europe’s largest active volcano, and at over 11,000 feet high, 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 of Monte Nero and the Bottoniera, or through the Linguaglossa pine forest, crossing a corridor of hardened lava flow. Weather permitting, you are treated to a Sicilian-style picnic lunch of crusty bread, sun-soaked tomatoes, fruit, local meats, and cheeses.

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

DAY 4

Following breakfast, a 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, glistening freshly caught fish, hams and cured meats. You help your guides pick out the day’s picnic supplies in this lively atmosphere.

By mid-morning, 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. Dramatic and fragrant, you walk through a river-carved landscape of limestone formations luxuriant in Mediterranean vegetation.

After a picnic lunch, you continue on a 1½-hour drive to Caltagirone, where you spend one night at a 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 is served in the dining room. A starter of Sicilian-style eggplant caponata may be followed by a succulent roast leg of pork, perfectly paired with local Nero d’Avola red wine.
Agriturismo Vecchia Masseria, Caltagirone

DAY 5

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 their abundance on the mountain in ancient times. Settled from the prehistoric age until the present, the 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 take leave of it and drive a few miles away to the town of Piazza Armerina, a pleasant provincial market town with a charming historic center of ancient palazzi inside a labyrinth of bustling streets. A very short drive takes you to the true jewel of the area—the magnificent Villa Romana del Casale, considered the most important Roman archeological site in Sicily. This Roman villa or hunting lodge was built approximately at the turn of the 3rd and 4th centuries (A.D.) and is known for its extraordinary collection of mosaics, in various stages of restoration. A UNESCO World Heritage site, 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 different aspects of everyday Roman life.

Concluding your visit, an approximate 2-hour drive brings you to the beautiful hillsides surrounding Castelbuono, an idyllic town around a 14th-century castle, and 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.

For dinner this evening, you start off with a stroll around the town of Castelbuono, stopping for an aperitivo before dinner at a nearby restaurant.
Relais Santa Anastasia, Castelbuono

DAY 6

Today you discover the lush natural reserve of the Parco Naturale Regionale delle Madonie, the Madonie Mountains regional park, just 20 minutes 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, it 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 are available in the park depending on the weather and the group’s interest; and depending on the chosen route, lunch could be authentic Sicilian fare in a traditional stone refuge or a trailside picnic lunch.

After a full day of exploring the park, you return to your hotel in the late afternoon to relax and perhaps enjoy the swimming pool. 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

DAY 7

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 historic sites such as the magnificent cathedral from the Norman era. Depending on the weather, the guides may choose a late morning walk to ascend La Rocca, a massive crag towering to 912 feet. The climb is steep, but short (taking approximately 30 minutes). After absorbing the magnificent coastal vista, you descend to the Temple of Diana, built between the 4th and 5th centuries B.C., below which still stand the fortified walls of the Byzantine period.

Following lunch at a local restaurant in Cefalù, you drive two hours to Segesta and a marvelous Doric temple dating to 430 B.C. alone in a field, amazingly one of Italy’s best-preserved ancient temples. The route then leads to a remarkable Hellenistic theater high on the mountain, where you bask in splendid views of the hills and Castellammare del Golfo. Founded by the Elymians, a mysterious ancient people, the city was fought over for centuries before eventually being conquered by the Romans. Depending on the morning’s walk and conditions, you may do a longer walk at this site, taking you up to Mount Barbara.

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 historic site associated with fertility goddesses—the Carthaginians’ Astarte, Greek Aphrodite, and Roman Venus. Arriving through a maze of medieval streets, tiny piazzas, churches, and baroque flowering balconies to Erice’s enchanting historic core, you reach your hotel for the night—a former private palazzo with frescoed ceilings. A lovely place to explore, your guides provide restaurant suggestions for dinner on your own nearby.
Hotel Elimo, Erice

Day 8

Following a breakfast of traditional Sicilian pasticcerie, such as cuccia (an Arab cake of grain, honey, and ricotta), you set off for an in-depth tour of the medieval town of Erice. Home to the Ettore Majorana Scientific and Cultural Institute, the town invites exploration of its sites, such as 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, in turn 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.

In addition to its rich history, Erice is famous throughout Sicily for its pastries. Nearing the end of the walk, there might be time to stop at the famous Pasticceria Di Grammatico Maria, the shop of a former nun turned pastry-maker, also the author of a memoir of her girlhood and time in a convent.

A late-morning 45-minute transfer delivers you to today’s walk in the Riserva Naturale dello Zingaro, a preserved natural area that comprises several miles of unspoiled coastline on the Gulf of Castellammare flanked by steep mountains. Created in 1980 after a successful protest halted a road construction project, the reserve features several well-maintained paths, six beaches, secluded bays and steep cliffs, and diverse flora and fauna. Several species of raptors, such as the peregrine falcon and buzzard, mate and nest in its secluded habitat, and it also contains an archeological site of prehistoric settlement. The setting is perfect for a delicious picnic lunch of savory local cheeses, breads, olives, and fresh fruit.

Finishing up the walk, you transfer 1½ hours south to the countryside of Menfi and your home for the next two nights at a vineyard-side resort. Each individually decorated guest room opens onto private terraces with views over herb and flower gardens and vineyards. Following a welcome aperitivo you proceed to dinner at a lively seaside restaurant just minutes from the hotel. One of the region’s best, its charismatic chef serves up the freshest catch of the day—be it calamari, clams, mussels, or swordfish—combined with luscious Pachino tomatoes, fresh herbs, and pasta or couscous.
Planeta Estate - La Foresteria, Menfi

DAY 9

After breakfast in your tranquil resort, you drive about 30 minutes to the town of Sambuca in Sicilia, to the Ulmo Winery and vineyards, also owned by the Planeta Estate. The 17th-century farmhouse that houses the vineyard’s office is also the family’s original home, and it stands between the ruins of an Arab castle, Arancio Lake, and a mountain range. Planted in over 200 acres of vines, the winery produces quality white wines including Chardonnay and Cometa, and to better share the lovely natural setting, they have designed a network of trails in and around the vineyard. Ascending through vineyards and woods, the path skirts the stone ruins of old houses surrounded by Shiraz vines, then at the highest point, views open up to both the sea and Arancio Lake. Winding back through fragrant vegetation of bay laurel, Mediterranean willow, and buckthorn, you return to the winery’s canteen for a tasting of Planeta wines paired with a light lunch.

After this tasting, you drive about an hour to Selinunte, an ancient city that is now one of Sicily’s most dramatically sited Greek ruin complexes. This city, of which the 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.

A 30-minute drive returns you to your hotel, with time to pack, relax, and perhaps swim in the hotel’s panoramic outdoor swimming pool. Later you gather for a farewell aperitivo and dinner on site. You toast your discoveries of enchanting Sicily over superlative cuisine served at a large communal table in the hotel’s dining room, or, weather permitting, al fresco on the terrace overlooking the vineyards, accompanied of course by the estate’s renowned vintages.
Planeta Estate - La Foresteria, Menfi

DAY 10

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

Itinerary Changes

Please 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.

Nights 1, 2 & 3

Hotel Domus Mariae Benessere
Siracusa, Italy

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 terrace overlooking the sea.

Night 4

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. This 4-star property is a member of the “Charm and Relax” group of Italian hotels.

Nights 5 & 6

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 from its own farm produce.

Night 7

Hotel Elimo
Erice, Italy

In the historic center of Erice, a renovated family-owned palazzo offers lovely rooms with frescoed ceilings and antique furnishings, a wine bar, terrace with view for outdoor dining, and interior garden.

Nights 8 & 9

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.

Please note that this is a sample hotel itinerary for this tour. While these exact hotels are featured on most departures, we occasionally reserve other hotels of similar style and quality. If you are currently booked on a Country Walkers adventure, a hotel itinerary has been sent to you for your exact departure date. Please call Country Walkers at 800.464.9255 if you have any questions about the exact hotels selected for any of our tours.

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.

Alex Gullo

Alessandro 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.