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Experience a historical and culinary feast on this tailor-made Sicily vacation! Beginning in Palermo, discover a mecca of ancient architecture, imposing buildings, rich art and culture, and a vibrant food scene. Explore the beautiful Sicilian countryside on a private excursion as you drive down to Cefalu to sample delicious wine at an award-winning winery. In the resort town of Taormina, perched upon a hill by the Mediterranean, witness grand architectural feats including ancient Greco-Roman ruins, framed by Mount Etna in the distance. This is also your chance to delve deeper into Sicilian cuisine with a personalized cooking lesson with an expert chef! En route to your next destination, visit Syracuse and Ortigia, where ancient ruins, art, and architecture await you. Finally in Ragusa, explore UNESCO-listed sites with a private guide in Ragusa Ibla, with well-timed breaks to sample more Sicilian food and wine!

With the top three destinations included in this private tour of Sicily, soak in a diversity of culture, landscapes, and flavors in a land prized by civilizations through time. Customize this Sicily vacation to match your interests and pace by getting in touch with us today!


Itinerary Summary

DayPlaceHighlightsHotel Options
1 - 3PalermoArchitecture, History, Street FoodHotel Plaza Opera, Excelsior Palace Palermo
3 - 6TaorminaHiking, Wineries, Landscapes & Mt EtnaHotel Villa Diodoro, NH Collection Taormina
6 - 8RagusaSicilian Baroque Architecture, Old Town, Traditional CuisineSan Giorgio Palace Hotel, Locanda Don Serafino

Ideal For

  • Heritage
  • Wine & Food
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Itinerary Details

Day 1 - 3

International Arrival

You will be transferred from Palermo airport to your hotel in a private vehicle


2 Nights

Palermo, the largest city on the island of Sicily, has stood the test of time since the ancient ages, straddling the cultures of the Occident as well as the Orient. The imposing buildings of the Palermo Cathedral, the Palazzo dei Normanni and the Cappella Palatina point to the city’s heyday in the Middle Ages.

Included Activities

On a Food Trail in Palermo
Tease your taste buds with Palermo’s popular culinary delights on this enjoyable street food tour. Reach Teatro Massimo bright and early to meet your local food guide for the day. Stroll along the main squares and street markets of Palermo’s city center, sampling delectable street food as recommended by your food guide. Sample the region’s authentic flavors and textures as you walk down the heart of town, learning more about the culinary history and traditions of Palermo. Discover hidden gems and pick up fascinating trivia from your guide along the way. Return to your hotel at the end of a most insightful food trail! (Half Day; Time: 0900 hrs; Private Activity; Food tasting/sampling included; Fitness level: Easy; Please wear comfortable walking shoes and be sure to inform ahead of time regarding any food allergies).

A Trip to Cefalù with Wine Tasting at Castelbuono
Experience the taste of this distinctive corner of Italy with its fascinating West Asian heritage and culture! Enjoy the wonderful drive down to Cefalù from your hotel, passing by the picturesque Sicilian landscape along the way. Take a leisurely walk to a charming little medieval Arabic village along the lovely Mediterranean coast and beachfront and observe how the ancient homes face the sea. Visit a typical old homestead and admire its fascinating architectural details. Stroll down the winding alleys and pay a visit to the stately Cathedral. Continue to an ancient abbey and award-winning winery tucked away in the Castelbuono countryside. Stop here for a well-deserved lunch break and a delicious wine tasting session. Learn all about the region’s vineyards and wine traditions as you relish the aromatic flavors of the local distillery. (Full Day; Time: 0900 hrs; Private Activity & Transfer; Wine tasting & Lunch included; Fitness level: Easy; Please wear comfortable walking shoes and inform ahead of time regarding food allergies, if any).

Hotel Options
RoomDeluxe Room
RoomClassic Room
Day 3 - 6

Your chauffeur will drive you from Palermo to Taormina in a private vehicle (Duration: 3 hrs)


3 Nights

Taormina is a spectacular combination of natural and ancient Grecian splendor. This ancient Sicilian town sits prettily atop a picturesque hill by the Mediterranean shore, overlooking the active volcanic mountain of Mount Etna.

Included Activities

Walking through Taormina
Watch the ancient Sicilian town of Taormina come alive on this walking tour! After breakfast in your hotel, make your way to Porta Messina, where you meet your guide for the day. Enjoy strolling down the old stone-paved streets and winding alleyways of this beautiful resort town, discovering hidden gems and picking up fantastic trivia from your guide along the way. Take in the medieval villas and the town’s celebrated archeological monuments and get to know the town’s best eateries, cafés and ice cream bars as well. Wind up your tour with an iconic view of Sicily’s largest ancient amphitheater, framed by Mount Etna in the distance and the Mediterranean coast stretched out before you. (Duration: 3.5 hrs; Time: 0930 hrs; Private Activity; Transfer Not Included; Fitness level: Easy; Please wear comfortable walking shoes).

Personalized Cooking Class with Market Visit
Master the art of Sicilian cooking in this private class under the guidance of an expert chef. Set off for the local market to pick up fresh ingredients for your culinary journey. Head to the restaurant Nettuno, armed with your pickings, to start preparing a typical local meal. Dice and chop under the watchful eye of the chef as you whip up an appetizer and a side dish before moving on to preparing pasta. Pick up the techniques of kneading dough the right way for the popular local dessert cannolo with its filling of ricotta and sugar. Learn to cook fish the Italian way as your chef regales you with interesting facts and anecdotes. Afterward, sit down with the chef to lunch on the delicacies you have concocted before it’s time to head back. (Duration: 5 hrs; Lunch Included; Private Activity; Private Transport; Fitness Level: Easy.)

Hotel Options
RoomClassic Room
RoomSuperior Room
Day 6 - 8

Your chauffeur will drive you from Taormina to Ragusa in a private vehicle. Enroute you will visit Syracuse (Duration without stops: 2 hrs)


2 Nights

Ragusa, a lovely hill town in Sicily, has two distinct characters. While Ragusa Ibla is the historic old town with its plethora of baroque architecture, winding hillside streets, and grand central plaza, Ragusa Superiore is its modern urban avatar with museums and malls.

Included Activities

Day out at Syracuse and Ortigia
On your way from Taormina, enjoy a day out amid the archeological wonders of Syracuse and visit the island of Ortigia. After an early breakfast in your hotel, drive down to the ancient town of Syracuse. Meet your local guide before walking out among the spectacular ruins. Watch the region’s rich heritage come alive as your guide takes you through the history and splendid arts of the Greco-Roman, medieval, Renaissance and Baroque periods. Pay a visit to the town’s ancient theatre, which continues to put up plays and performances to this day. Drive down to the lively little Sicilian island of Ortigia next. Stroll down the pretty cobblestoned streets of this charming old town. Don’t miss the historic city center, before arriving at your hotel in Ragusa. (Half Day; Time: 0830 hrs; Private En route Activity & Transfers; Fitness level: Easy; Please wear comfortable walking shoes).

Discovering Ragusa’s Historic and Culinary Heritage
Watch the Sicilian hill town of Ragusa come alive before your eyes! After an early breakfast in your hotel, drive down to Ragusa Ibla. Meet your local guide, before strolling around one of the most fascinating towns in Sicily. Enjoy walking along the UNESCO World Heritage site of Val di Noto and visit a host of the town’s heritage buildings protected by UNESCO. Take in the grand Baroque art and architecture of the city, discovering hidden gems and picking up trivia from your guide along the way. Stop to enjoy a leisurely lunch break at a traditional trattoria, feasting on local Sicilian dishes, washed down with delicious Sicilian wine. Drive back to your hotel after an enjoyable meal. (Full Day; Time: 0900 hrs; Private Activity & Transfer; Lunch included; Fitness level: Easy; Please wear comfortable walking shoes and inform us in advance of food allergies, if any. Entrance fees are not included.).

Hotel Options
RoomClassic Room
RoomStandard Room

You will be transferred from your hotel to Catania airport in a private vehicle

International Departure

 Price & Inclusions

  • Option 1 From $ 4,290 /person
  • Option 2 From $ 4,890 /person

Prices are in USD and exclude international flights. This trip price is based on low season rates for accommodation and other applicable services, and may change depending on availability, currency fluctuations and number of people traveling together. For high season prices, please contact us with your exact travel dates and preferences.

Price Includes

  • Accommodation and meals, as specified in the itinerary
  • Activities and excursions, as specified in the itinerary
  • Transportation services, as specified in the itinerary
  • Your Trip Coordinator: a 24/7 point of contact supporting you during your trip
  • Carbon emissions offsetting for your trip

Not Included

  • Entrance fees and meals, unless mentioned in the itinerary description
  • Tips and personal expenses
  • Visa and tourism fees
  • Travel, health and cancellation insurance
  • International airfare
Inquire Now
Sicilian Cuisine and Heritage

8 days $ 4,290 / person