Soul of Sicily

  • Sample Itinerary
  • Experiences
  • Pricing
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A crossroads of culture from the ancient Greeks and Romans to the Normans, Arabs and Spanish, you will explore Sicily’s most luminous landscapes to uncover the soulful essence of the island. From the ancient seaside villages of Siracusa and Taormina to the fertile foothills of Mt. Etna, and the Baroque palaces of Noto to the sophistication of Palermo, discover the beguiling heritage of the Mediterranean’s largest island.

Sample Itinerary

Day 1

Upon arrival to Palermo, be welcomed by your private chauffeur and depart for your 19th century palazzo turned five-star hotel, located just minutes from the dazzling Teatro Massimo opera house. In the evening get acquainted with the flavors of Palermo, such as Pasta con le Sarde and fresh swordfish, with dinner at a chic trattoria in the heart of the city.

Day 2

This morning you’ll set off on a privately guided exploration of Palermo’s architectural marvels with a local expert. Experience the Palazzo dei Normanni with its UNESCO designated Byzantine mosaics, before exploring the city’s lush Villa Bonnano park and Cathedral, merging Norman, Moorish, Gothic and Baroque architecture. Stop for lunch at a noted osteria before admiring the city’s signature Baroque fountains, opulent piazze, and storied Teatro Massimo Opera House. Crown the afternoon with a sweet repose as you sample one of the city’s most delicious cannoli and other sweet treats, at a chic cafe beloved by the locals.

Day 3

Today discover Palermo’s vibrant city life with a guided visit through the colorful Ballaro market. Experience its kaleidoscope of fruits, vegetables, and treasures from the sea, before savoring lunch at a historic eatery. Next, travel to the noble palazzo of an aristocratic family, dating back to the medieval period, where the Countess will welcome you with a tour of her exquisite home while sharing her family’s unique history. Crown your visit with typical Sicilian hors d'oeuvres paired with wine produced by the family. End the day by experiencing the Sicilian tradition of the Opera dei Pupi (Sicilian puppet theater). Visit the private workshop of a third generation master puppeteer before delighting in a special evening performance at the puppeteer’s whimsical theater.

Day 4

Whisk away to the mountaintop village of Monreale where a local expert will guide you on an in-depth exploration of its Cattedrale di Monreale and adjoining cloister. A magnificent confluence of Norman, Arab and Byzantine art, you’ll discover the cathedral’s UNESCO designated mosaics from the 12th century, and experience the serenity of its exquisite cloister, one of the finest in Italy. You’ll next visit the ancient coastal town of Cefalu to take in its picturesque lungomare and antique fishing port. Delve into the beauty of its Norman and Byzantine past with a guided visit of the town’s extraordinary Cathedral of Cefalu, before admiring its lovely pedestrian center of cobbled streets and scenic piazze. Along the way, enjoy lunch at a charming eatery featuring local seafood and panoramic views of the water.

Day 5

From Palermo set off for the sweeping archaeological site of Segesta. With the help of a local expert you will explore its Doric temple dating back to 420 BC, and breathtaking Greek theater, while learning about its significance as a center for Sicily’s indigenous Elymian people. Your chauffeur will next transport you to Trapani to enjoy a lunch featuring the town’s signature recipes. Embark on a private walking tour of the town’s Baroque center adorned by 15th century churches and noble palazzi, before a scenic stroll along its quaint seafront. Be transferred to your luxury wine resort for check-in, and settle-in with a special tasting of estate wines paired with gourmet delights prepared by the chef.

Day 6

Travel to the estate of a revered wine making family dedicated to the preservation of the region’s ancient varietals and authentic traditions for producing high quality Marsala Superiore and Grillo wines. Set off on a private tour of the estate to learn about the depth and complexity of fine Marsala, before tasting the producer’s stellar wines. Afterward, depart for a renowned restaurant celebrating the flavors of the Trapani province with a contemporary perspective. After lunch, be transported to the town of Marsala to explore the walled environs of its historic center at your leisure.

Day 7

Depart for the picturesque countryside surrounding Menfi where you’ll arrive at an acclaimed olive oil producer known for their exceptional estate bottled extra virgin olive oils. During your private visit you’ll learn about the estate’s traditional production methods followed by a tasting of their premium quality oils and other specialty gourmet products crafted by the family. Next, travel to the colorful village of Sciacca to dine at an acclaimed Slow Food designated restaurant whose refined menu showcases seasonal offerings from local producers. In the afternoon your chauffeur will transport you to Agrigento for arrival to your luxurious five-star hotel exclusively located within the Valley of the Temples.

Day 8

Embark on a day of archaeological discovery as your expert archaeologist helps you uncover the intriguing history of the Valley of the Temples. A superior example of Greek Doric architecture, the Valley of the Temples is a UNESCO designated treasure, offering visitors an extraordinary glimpse into ancient Greek civilization. During your fascinating exploration of the archaeological site, you will stop to admire such sites as the majestic Temple of Concordia, and the remains of the Temple of Heracles and Temple of Zeus, all dating back to the 5th century B.C. Travel to a neighboring coastal village to take in stunning views of the sea while enjoying a sumptuous meal inspired by the season.

Day 9

From the ancient Greeks to the ancient Romans, today you will set off for Piazza Armerina, a town that came to particular prominence during the Roman and Norman periods. Your expert archaeologist will guide you on an in depth exploration of the city’s famed Villa Romana del Casale, a UNESCO World Heritage site. A luxurious Roman villa dating back to the 4th century, you’ll discover its acclaimed wealth of pristinely preserved mosaics, deemed the finest examples left in existence from the Roman period. For lunch you’ll savor rustic dishes from Sicily’s interior before being transferred to Ragusa for check-in to your opulent five-star hotel located within an 18th century palace.

Day 10

Explore the Baroque heart of Ragusa Ibla with your local expert before arriving at an esteemed two-Michelin starred restaurant, regarded as one of the finest in all of Sicily, for an exclusive dining experience. Depart by chauffeur for the Baroque grandeur of Modica to explore its resplendent swirl of churches and palaces designed in the Sicilian Baroque style, during a private walking tour. Next, experience the town’s fabled chocolate making tradition with a visit to the home of a local food expert. Learn how the town’s signature sweet has through the centuries retained it strong ties to the New World during a chocolate making lesson and sampling of local treats. End the day with a behind the scenes visit to the town’s most esteemed chocolatier, Antica Dolceria Bonajuto, to delight in a tasting of their sensational confections.

Day 11

From Ragusa you will set off to explore Noto, the capital city of Sicilian Baroque. With the help of your local guide, discover the town’s magnificent series of palaces and churches, and its main street of Corso Vittorio Emanuele, showcasing glorious 18th century Sicilian Baroque architecture. Along the way, stop at a famed gelateria to taste their innovative flavors handcrafted using seasonal ingredients. Travel to a winery located in the surrounding countryside for a special wine tasting before relaxing with a lovely picnic on the estate. Your chauffeur will next transfer you to the ancient city of Siracusa for arrival to your elegant four-star hotel located on the idyllic island of Ortigia.

Day 12

Spend the morning exploring Ortigia, the jewel that is the historic heart of Siracusa. Your local expert will lead you along the town’s panoramic waterfront and atmospheric center traversed by medieval lanes and Baroque palaces, and punctuated by the extraordinary Piazza Duomo. Stop to admire Caravaggio’s famed Burial of St. Lucy masterpiece before enjoying a lunch of local specialties with a modern twist at a gourmet eatery. Spend the afternoon delving into Siracusa’s ancient Greek past with a guided visit of its Greek Theater and stone quarry, the Latomia del Paradiso.

Day 13

From Siracusa you will whisk away to the imposing slopes of Mt. Etna. Led by an expert vulcanologist, you will embark on a one of a kind exploration of some of Mt. Etna’s most fascinating villages, while discovering the vulcano’s unique flora. Along the way visit an organic bee farm to learn about the area’s traditional honey production before tasting the farm’s high quality honey varieties infused with the essence of the surrounding flowers and herbs. After a hearty lunch inspired by the fertile landscapes of the Etna, travel to the stunning hilltop town of Taormina with sweeping views of the Mediterranean. Arrive at your sumptuous five-star hotel, an iconic landmark of sophistication, for a relaxing evening at your leisure.

Day 14

Your chauffeur will arrive in morning and you’ll depart for the tiny hilltop town of Castelmola, designated as one of Italy’s most beautiful villages. Home to exquisite Norman architecture, you’ll meander along its scenic cobbled streets while taking in extraordinary views of Mt. Etna and the coastline. Sample the locally produced Vino di Mandorla (Almond wine) before returning to Taormina for free time to explore the city’s Roman amphitheater, have lunch, and shop along Corso Umberto, independently. In the evening, celebrate your time in Sicily with an elegant dinner of creative, modern Sicilian cuisine at your hotel’s acclaimed two Michelin-starred restaurant, Principe Cerami.

Day 15

After breakfast bid farewell to your glorious perch above the sea and depart by chauffeur for Catania Airport, in preparation for your return flight or the next leg of your adventure.

Experiences We Recommend

  • Private walking tour of Palermo’s UNESCO designated Norman & Moorish palaces, including Palazzo Normanni
  • Guided walk through the Ballaro & Vucciria markets in Palermo
  • Private visit to the noble home of Sicilian countess
  • Art tour of UNESCO designated mosaics of Monreale’s Cathedral
  • Archaeological site visit of Segesta
  • Winery tour & tasting at exclusive producer of Marsala Superiore wine
  • Owner-led tour of renowned extra virgin oil mill with tasting
  • Archaeologist-led private tour of the Valley of the Temples in Agrigento
  • Privately guided architecture tour of the Baroque palaces of Ragusa, Modica & Noto
  • Private chocolate making demonstration & sampling in Modica
  • Exclusive winery visit & picnic lunch at estate of renowned Nero D’Avola producer
  • Art & history walking tour of Siracusa’s historic Ortigia island
  • Vulcanologist led tour of Mt. Etna’s villages
  • Visit to organic honey farm with tasting on Mt. Etna


The minimum trip length for a CountryBred Encounter is 5 Days/4 Nights

Pricing for our Italy Encounters begins at:

  • $850-$1,000/per person, per day* based on double occupancy and a travel party of two
Small group pricing available for travel parties of four or more

*The final price of your custom tour will be determined by your travel party size, departure dates, trip length, amount of meals included, percentage of guided time requested, cities chosen in your itinerary and signature CountryBred excursions selected. This sample itinerary can also be crafted for solo travelers.

Encounters Include

  • Stays at five & four-star boutique luxury hotels
  • Chauffeured transport for touring & transfers
  • Private touring with professional local guides
  • Engaging activities led by cultural experts
  • Signature experiences with insider access
  • Regionally authentic dining
  • Traveler Welcome Package
  • Taxes & base gratuities

Read Client Reviews

  • Kevin C.

    Grand Getaway to the Amalfi Coast & Sicily
    CountryBred delivered an experience that was above our expectations. Hotels, Meals, Transportation, Tour Guides etc. were best in class.
  • Gay B.

    Alentejo to Lisbon
    Above and beyond our expectations for an amazing well organized adventure for 26!!
  • Mark W.

    From Castilla to Basque Country
    Our third CountryBred travel experience guided us through the rich cultural history, food, wine & unique culture throughout central/northern Spain. Our selected experiences coupled with the region/city ambassadors throughout our trip were exceptional and made our experience GREAT! (hotels too!)

Crafting the Experience

Experiential travel takes time, passion and local ingredients to make something truly special.

Read more


We turn travel inspiration into unforgettable journeys. Begin the trip design process by filling out the form below and a CountryBred specialist will contact you to get your next great adventure underway.


  • CountryBred Encounters begin at $750-$1,000/per person, per day
  • The minimum trip length for a CountryBred Encounter is 5 Days/4 Nights
  • All CountryBred Encounters are land touring experiences only and do not include airfare
  • Groups of four or more are eligible for small group pricing


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