Sicily is a captivating Italian island and a destination that draws you back again and again. Quintessentially Mediterranean, Sicily is a mix of many civilizations and a crossroads of trade and commerce since ancient times. The Ancient Greeks founded many of Sicily’s most famous towns, including Syracuse, Catania, Taormina, Giardini Naxos, and Messina. Phoenicians, Romans, Arabs, Normans, the Spanish, and the French followed. It is precisely this mix of cultures that make Sicily so unique and appealing. The island’s architecture is rich and varied, and the food is to die for! Sicily is a lot larger than many visitors expect, and there is so much to see and do, from wine tasting to visiting ancient Greek ruins to sailing out to volcanic islands. There are over 1400 kilometers of coastline in Sicily! We have designed this itinerary to show you the “best of the Island,” including the spectacular Aeolian Islands.
This premium, private wine tour in Sicily includes both the western and the eastern part of the island and offers a variety of food, wine, and cultural experiences. Visit the one and only Palermo, chic Taormina, Greek Syracuse, trapped-in-time Agrigento, and baroque Ragusa. Enjoy personalized, VIP wine tours and tastings in Marsala, Etna, Vittoria, Castelbuono, and other smaller wine regions. Pamper yourself with spa time at exquisite resorts. Your adventure begins in Palermo, and for the next few nights will be staying at the historic Villa Igea, where you might run into visiting celebrities. Just over a mile outside of Palermo’s historic center, this is a relaxing place to stay while in the Capital. Highlights include the seaside town of Cefalù, the Greek Temples of Agrigento and Segesta, ceramics of Caltagirone, and mosaics of Villa del Casale.
You will also visit Caltagirone, the city of ceramics, and medieval Erice, perched on Mount Erice overlooking Trapani. Its Norman castle and citadel rest on rugged mountains, and Erice called “city in the clouds.” You will experience wonders of nature, like Mount Etna and Scala dei Turchi. Wine tasting at top Sicilian cellars is in store for you on this tour, and you will visit leading estates like Abbazia di Sant’Anastasia, Marco de Bartoli, Gulfi, Tenuta Delle Terre Nere, Biondi, Passopisciaro, COS, and Armosa. Marvel at the sea salt mounds near Trapani and indulge in sea salt spa treatments, including a private salt bath.
Finally, it wouldn’t be a Cellar Tours vacation without some unforgettable gourmet experiences and dining, and you will taste an array of traditional local dishes. Including Crespelle di Ricotta e Acciughe (sinfully delicious deep-fried ricotta and anchovies); Caponata (a sumptuous eggplant/aubergine antipasto); Pasta Alla Norma (pasta with a savory eggplant, ricotta, and basil sauce); one million variations of Pesce Spada (swordfish) and (believe it or not), seafood couscous, particularly in Trapani area, a reminder of Sicily’s Arabic past. Sicily also has a sweet tooth and relishing freshly made Cassata is one of those “must-do” experiences in life. This tour combines unique sightseeing, luxury, and plenty of wining and dining!
Signature journey
Highlights include Visit the Best of Sicily from coast to coast, Luxury Hotels and Spa, Private Luxurious Mercedes Chauffeured Tour, and Wine Tasting at top Sicilian estates.
Day 1Palermo
The beautiful churches of Palermo
Arrive at Palermo airport or port, and your friendly driver-guide will be waiting to drive you to your luxurious hotel in Palermo, an Art Nouveau castle facing the Gulf of Palermo.
Discover Palermo and Monreale and enjoy an afternoon guided walking tour of the enchanting 12th-century Cathedral (with additions made in the 1700s), Palatine Chapel, Quattro Canti, Teatro Massimo, and nearby gourmet shops. The unique Martorana Fruits (Marzipan shaped to look like real fruits) come from Palermo, and there are a few unique, historic shops where you can pick up these and other gourmet goodies (great gifts). Carry on to Monreale to visit the enchanting UNESCO site Norman-Byzantine cathedral. Enjoy your knowledgeable guide’s stories about Monreale and Palermo’s legends and idiosyncrasies.
In the early evening, you will head back to your hotel to freshen up and then enjoy welcome dinner in the heart of ancient Palermo, at Palazzo Gangi. In a warm and welcoming atmosphere, you will taste dishes like Cuttlefish, couscous with seafood, oyster, wild asparagus and lemon zest; Anelletti pasta from Palermo, white octopus ragout, black beans, snow peas; crispy red mullet, “Sfincione” sauce, white and red Tropea onion, paired with excellent wines.
Benvenuti in Sicilia!
Day 2Palermo – Cefalù – Castelbuono - Palermo
Beautiful old harbor in Cefalu
This morning you will discover Palermo’s vibrant atmosphere. Start the day with a tour of the Ballarò market, with your private chef. It is the oldest food market in Palermo, in the Albergheria Norman neighborhood. You will visit the market stalls, immersed in colors, flavors, fragrances, and ‘abbanniate,’ the local dialect word for the yelling of the sellers. Next is a hands-on cooking class demonstrating the “monsù,” originally a French style of cooking but adopted by the Sicilian chefs for the aristocratic families of Palermo many years ago.
Once you have finished lunch dining on your delicious creations, your driver will take you to the famous Norman town of Cefalù. About an hour drive east of Palermo passing the ancient sites of Solunto and Bagheria. Cefalù is a small alluring town facing the sea. Your private guide who will take you on an exciting tour through the winding medieval streets and, of course, into the striking cathedral.
Your day will end with a great wine experience at Abbazia Sant’Anastasia. You will taste organic and biodynamic wines, paired with chef Alessandro Battaglia’s genuine Sicilian cuisine. On the menu today is Insalata di arance (orange, fennel, and marinated olive salad), arancini – rice balls stuffed with Pecorino cheese and meat), Bucatini con le Sarde (pasta with sardines) and then finish off with some just-made cannoli.
Transfer back to your hotel.
Day 3Palermo- Segesta- Erice- Marsala – Mazara del Vallo countryside
Norman castle in Erice
A tour of the best of the west is on the program today. From Palermo, your chauffeur will drive you southwest to Segesta, an Ancient Greek settlement. You will gaze with wonder at the Doric Temple resting peacefully in a grassy field for the last 2500 years. Enjoy an hour or so in the archeological park before carrying on to mystical Erice. An extraordinary little village! Overlooking the sea and high in the hills, you could almost easily mistake Erice for a Sicilian version of Camelot with its coastal fog and fairytale castles. From Erice, you can see the Egadi Islands, which make an exciting excursion if you wanted to add a day to this itinerary.
Savor some free time to explore Erice’s maze of medieval stone streets on your own. There are many beautiful panoramic spots to take in the views, and a visit to the mythical pastry shop La Pasticceria di Maria Grammatico is a must.
You will have a tantalizing pranzo “lunch” today at the restaurant Monte San Giuliano. Chef Matteo Giurlanda will prepare some of the best pasta you will taste in your life, paired with excellent local wines such as the ones from Firriato estate.
After lunch, head towards Marsala. On the way to Marsala, you will pass by the unusual and impressive sea salt mounds. Stop for a quick visit at the Saline Ettore Infersa Saltworks, a producer and vendor of super high-quality sea salt. Enjoy a short, fascinating tour!
While Marsala history dates back to ancient times (there is a Roman-era Archaeological Park outside of the town), Marsala was bombed heavily during WWII, and much of the city’s architecture now is lackluster concrete tower blocks built in the 1960s. You might pass through without stopping if you didn’t know the wine treasures that lie hidden from sight.
You will visit one of the top-quality artisanal wineries of the area: Marco de Bartoli. You will have a unique experience with great wines and people that will change your idea about Marsala wine.
In the evening, you will drive towards Mazara del Vallo countryside to your spa resort. Tonight is yours to relax and dine on your own, or order room service tonight and make it unique with a few candles and some fabulous wine. The perfect rooms have some of the most comfortable beds you have ever had the pleasure of experiencing.
Day 4Mazara – Menfi area – Mazara
Luxury suite at Spa hotel
After a superb breakfast, you will travel inland towards the Menfi countryside for excellent olive oil experience and some wine tasting.
Start with a full immersion in olive oil: you will visit the olive grove and the olive mills and enjoy a tasting masterclass learning all about Extra Virgin Olive Oil, and then enjoy an authentic homemade Sicilian lunch on the terrace and under olive trees
Next, you visit a high-end estate Planeta. Planeta is one of Sicily’s leading wineries, and they make a stellar range of wines. You will taste four old vintages of their top wines, tough to find anywhere else.
On the way back to your luxury spa resort, you could stop in Selinunte a most if you were interested in archeology, or Alberto Burri landscape artwork of Cretto di Gibellina. Otherwise, you could get back to the hotel early to hit the spa. The night is yours to enjoy the resort, or you could take a taxi to dine at the nearby restaurant Da Vittorio, to taste the freshest and most delicious fish, right on the beach.
Day 5Mazara – Scala dei Turchi – Licata - Agrigento
Valle dei Templi in Agrigento
Leave your luxury hotel after breakfast and head to Agrigento. On the way, stop in Sciacca for a quick visit to this lovely fishermen village, famous for beautiful coral (excellent souvenir and perfect for gifts) and the “Castello Incantato,” the Enchanted Castle, an evocative open-air collection of Filippo Bentivegna’s art.
You will then visit a true wonder of nature, the La Scala dei Turchi, a spectacular stretch of white cliff coastline made from soft limestone and white marl, transformed by the sea and the wind over the millennia.
Next, you will head south to the 2 Michelin starred restaurant La Madia, where chef Pino Cuttaia will prepare for you some of his first-class dishes, including the to die for Nuvola di Caprese.
After this terrific lunch, you will then arrive at the jewel of this area of Sicily, the world’s most important archaeological site and a UNESCO heritage site: Valley of the Temples. With your private art guide, you will visit the temples of Concord, Juno, Heracles, and Zeus some of the most outstanding and extraordinary monuments of Greek art in the world.
End the day by settling into your luxury villa hotel. Dinner tonight could be at a gourmet restaurant of the hotel, with views of the temples.
Day 6Agrigento – Piazza Armerina – Caltagirone – Ragusa countryside
Mosaic tile in Villa Romana del Casale
Today after enjoying your delicious breakfast, you will head to the 15th-century Roman Villa del Casale and ceramics town of Caltagirone. With your charming art guide, you will visit the impressive Roman complex, “the superb remains of magnificent mosaics floors of the splendid villa from the late Imperial Age.”
Lunch will be a gourmet affair with chef Angelo, who will amaze you with dishes like panzerotti ceci e tartufo (pasta filled with potatoes and chickpeas, served with whitebait fritters and black truffle). For the main course, black pig fillet with wild asparagus paired with Cerasuolo di Vittoria and spectacular Ben Ryé Passito di Pantelleria (from the island of Pantelleria), and for dessert “delicious cassata”.
Carry on to Caltagirone, “the city of ceramics,” famous worldwide for its ceramics. Ceramic production started here 1000 BC. If you visit in May, you will see the “Infiorata,” when the famous Caltagirone stairway is decorated with thousands of flowers in honor of the Madonna; in July, you will experience the feast of the Holy Patron, with a parade of horses and historic carriages.
In the early evening, arrive at your peaceful boutique hotel.
Day 7Ragusa countryside
Delicious pasta alla norma
Today is all about wine! The first winery of the day will be COS, an exciting natural winery located in Vittoria, the home to the only Sicilian DOCG, Cerasuolo di Vittoria, which brings together the Nero d’Avola and Frappato varieties to make an exquisite, fresh, expressive red. You will also taste their wines aged in terracotta amphoras.
Next is Gulfi, an organic winery in Chiaramonte Gulfi, whose wines come only from indigenous grapes: Nero d’Avola, Frappato, Nerello Mascalese, Nerello Cappuccio, Carricante, and Albanello. Here, you will enjoy a full wine-tasting lunch. Pairing with black pork cured meat with crispy salads, baked ricotta, toasted bread, and fennel oil; Russello wheat cavati pasta, sausage ragout, and bread crumb; lamb rack with dry tomato sauce and capers pesto; Sicilian tiramisu with ricotta and pistachio.
To complete this perfect day, you will visit the Armosa organic vineyards and cellar guided by the owner and winemaker Michele. Taste “Siclys” and “Curma,” 100% Nero d’Avola grape, and Salipetrj, 100% Moscato Bianco grape.
Before going back to the hotel, visit the Donnafgata castle, where Luchino Visconti “The Leopard” movie was filmed, acting Burt Lancaster, Alain Delon and Claudia Cardinale.
Tonight you can relax at the hotel or explore on your own Unesco site Ragusa Ibla, dining at excellent Michelin starred restaurant Il Duomo.
Day 8Ragusa countryside – Baroque valley towns – Marzamemi - Syracuse - Taormina
Baroque town of Ragusa
Today you will head to the marvelous town of Taormina, but first, you will visit enchanting Val di Noto, a must-see in Sicily. After the earthquake that destroyed the eastern Sicily in 1693, eight towns (Caltagirone, Militello in Val di Catania, Catania, Modica, Noto, Palazzolo, Ragusa, and Scicli) were rebuilt in an exuberant late Baroque style. You will have your driver at disposal to explore the area. We suggest not to miss Noto, the heart of the valley, and Modica famous for its chocolate. It has a grainy texture; inspired by the Aztecs and, introduced to Sicily by the Spanish in the 16th century. Following a quick tour of Cioccolateria Bonajiuto, you will enjoy a full tasting simply divine!
Lunch will be in the picturesque fishing hamlet of Marzamemi, before heading to Syracuse. Your private guide will show you the archaeological park, including the Ancient Greek Theatre. (still used today for Greek drama performances in the summer) and the gigantic limestone cave, named “Ear of Dionysius” by Caravaggio. Your guide will also reveal Ortygia, the historical center of Syracuse, built on a small island. You will visit Arethusa fountain, beautiful palazzos, piazzas, and Duomo, a catholic church built on a Greek Doric temple. You will admire Caravaggio’s painting Burial of St. Lucy and learn about the special relationship between the town and its patroness.
Arrive in the early evening at chic and glamorous Taormina.
Day 9Taormina - Mount Etna - Taormina
Ancient Greek Theater in Taormina
Charm and adventure today! You will start with an exciting private Jeep tour of Mount Etna, the iconic Sicilian volcano and UNESCO site. Visit an incredible lava cave, Valle del Bove and Craters Silvestri, created in 1865 by lava flow. This excursion is private so that you can decide the pace and intensity of the tour.
Lunch will be a real highlight of the trip. With Ciro and Stephanie, you will enjoy an intimate, private tour and tasting lunch al fresco at one of the best wine estates on Mount Etna. An extraordinary place and great hosts.
Back to Taormina, you will meet your private guide for a walking tour of this dazzling town, including the magnificent Ancient Greek theatre, of course. Taste the best granita in the world, have fun trying as many flavors as you can: coffee, bitter almonds, black mulberries, pistachio.
Day 10Taormina - Mount Etna - Taormina
Passopisciaro wine estate on the slopes of Mt. Etna
Head back to Etna again today, but the focus will be on the high-end wines produced in this area. Over the last 15 years, this wine region has become one of Italy’s most exciting and dynamic. First, you will visit Marc De Grazia’s Tenuta delle Terre Nere winery and taste their astonishingly complex and fresh wines. Including pre-phylloxera La Vigna di Don Peppino, whose Nerello Mascalese and Nerello Cappuccio grapes come from 130 years old vines, which stand on their original rootstock.
You will stop for a light lunch with “pane cunzato” and other local delicacies, before arriving at the Passopisciaro wine estate, where you will taste their Contrade, different Nerello Mascalese wines. Finish the tastings with the exceptional Franchetti, a Super-Etnean wine made with Petit Verdot and Cesanese d’Affile.
On the way back, Taormina, stop in lovely Castelmola. This small village above Taormina is a real natural terrace built around the ruins of a Norman castle that, over time, has assumed a concave and smooth shape. From here, you here you will have spectacular views of the Ionian coast, the bay of Giardini-Naxos, Mount Etna, the strait of Messina, and the Calabrian coast. A breathtaking view you will never forget.
The rest of the day is yours to relax, go shopping, enjoy the Isola Bella beaches. If you prefer, we can organize a guided tour of the quaint, small villages, like Savoca and Forza d’Angrò, where Francis Ford Coppola filmed The Godfather.
Your gourmet, farewell dinner will be at a romantic Michelin starred restaurant, this is a memory maker!
Day 11Taormina – Catania
Buon Viaggio!
Today your driver will transfer you from your hotel to the airport in Catania. This concludes your once in a lifetime food and wine tour of Sicily.
Cellar Tours private itineraries include chauffeur-led transportation, carefully selected hotels, winery appointments, restaurant planning, and practical support before and during your journey.
Depending on the destination and proposal, your tour may also include private guides, tastings, special experiences, cultural visits, regional transfers, and dining reservations.
Your custom proposal will clearly show what is included, what is optional, and what is not included.
Our custom itineraries include chauffeur-led transportation, carefully selected hotels, private winery appointments & tastings, restaurant planning, and support before and during your travel.
International flights, travel insurance, personal expenses, optional spa treatments, gratuities and meals or tastings not listed in your itinerary are usually not included unless specifically stated.
All itineraries are private and pre-arranged for your party.
Yes, 100%. Share mobility considerations, allergies, dietary preferences, and pacing needs early so we can adapt hotels, transport, restaurants, and visits wherever possible.
Joan Cefali
Everything about the Ashbee was wonderful. 5* plus
Ciro Biondi was an amazing experience! The food was wonderfully simple and fresh. Absolutely delicious! Ciro and his wife. Cottanera was great. Again, simple, fresh and way too much. Il Duomo, OMG!, was over the top. The chef and staff were amazingly attentive and the experience was like no other. The driver Sebastiano is a sweetheart. He actually gave us some of his wine and fruit from his own garden. Siracusa Tour guide Enzo was very knowledgeable. He definitely went above and beyond my expectations. I would definitely recommend you again and again and again!!
Marsha and John Filice, La Selva, Califorina
We are now back home and I wanted to write and thank you.
Simona and your staff for another wonderful tour. The scheduling and planning were perfect and I know that requires familiarity with the area and locations. The winery selections were fabulous and we enjoyed meeting many owners and winemakers. All of your recommendations were on point. Every day was memorable. Our drivers and guides were personable and became our friends. I sound effusive, but my appreciation is real. Well done. We look forward to the next food and wine adventure.
Grazie mille, Jeanne Carpenter
Simona outdid herself with this one
Spending 12 days in Sicily, celebrating our 25th wedding anniversary, has been wonderful. The history and scenery is so inspiring and fascinating. All of our many guides, hosts and especially our driver, John, have made this trip a once-in-a-lifetime experience. We especially enjoyed our time with Ciro and Stephanie Biondi at their home in their Etna vineyard in Trecastagni. And of course, we can’t say enough good things about Simona at Cellar Tours, who has been planning trips for us for a decade. She outdid herself with this one.
