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

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 at an inviting trattoria in town.

Oasi Naturale di Vendicari and Noto; 4-7 miles, easy to moderate, elevation gain and loss of 70 ft

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, 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 an inviting local restaurant.

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, 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 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.

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. Dramatic and fragrant, you walk through a river-carved landscape of limestone formations luxuriant in colorful 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.

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 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 magnificent Villa Romana del Casale, considered the most important Roman archaeological 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 two-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.

This evening, there is time to settle in and enjoy the expansive property before dinner in the hotel’s elegant dining room.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 magnificent Villa Romana del Casale, considered the most important Roman archaeological 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. This evening, there is time to settle in and enjoy the expansive property before dinner in the hotel’s elegant dining room.

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, 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 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), built over the ruins of a pagan temple and whose crypt is 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.

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 historic sites. Following a guided visit to the town’s magnificent cathedral from the Norman era, 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. alone in a field, amazingly one of Italy’s best-preserved ancient temples. Founded by the Elymians, a mysterious ancient people, the city 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 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 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, 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.

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

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 archeological 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.  Afterwards 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. 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 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.

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, 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.

Nearing lunchtime, you return to your hotel for a light lunch of pasta and salad, followed by 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 breadsticks, crostini, and olives. A farewell dinner follows on the outdoor terrace (weather permitting), a perfect venue for toasting your discoveries of enchanting Sicily.

Transfer to Palermo. Departure

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.