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Originally from Toronto but now living in Italy, I’ve always been a traveler at heart. When I’m not planning your luxury European trip, you’ll find me hiking the Italian Alps or enjoying a lemon Spritz in Amalfi.
- from $4,707 PP
- 10 Nights
- Apr - Oct
- 2hrs from London / 9hrs from NYC
Sicily is a seductive island with everything from mountain, volcano, and Mediterranean scenery that provides a spectacular backdrop for all sorts of adventure to a 10,000-year history and a delectable array of culinary influences that results in some of the world’s tastiest cuisine. Discover it all in style on this 11-day, 10-night adventure that starts in the capital city of Palermo. Enjoy upscale 4- and 5-star hotels, private guided tours, a foodie excursion, and even a cooking class led by a Michelin-star chef. You’ll discover ancient sites and rich culture while getting local insight for a more authentic experience with plenty of time for relaxation and exploring on your own.
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Book your trip with us and pay a reduced deposit with the rest 90 days before your departure
If you are not comfortable traveling, you have the right to cancel and get a refund up to 45 days before your departure
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- 10 nights of 4- and 5-star accommodation
- Customized itinerary
- 24-hour staff support
- Half-day private tour of Palermo
- Half-day Tour Valley of the Temples & Kolymbetra Gardens
- Rural Sicily Food Tour with Lunch
- Private Syracuse & Ortigia Island Walking Tour
- Private walking tour of Taormina
- Michelin-star cooking class in Taormina
Day by Day Itinerary
Day 1 Palermo: Arrival into Sicily
Your 10-night adventure through Sicily begins in its oldest city and capital, Palermo, known for its impressive architecture with influences by everyone from the Romans and Greeks to the Spanish, Arabs, and Normans. It’s also famous for its street food and offers plenty for art enthusiasts too. You’ll be met by your private driver for a transfer from Palermo’s airport to your hotel where you can enjoy the remainder of the day resting up after your travels or perhaps wander through the Old Town to stretch your legs, gazing up at its magnificent centuries-old buildings, including baroque-style palazzos. Sampling some of its street food is a great intro into the cuisine, including delicious panelle (Sicilian fritters), arancini balls, and Croce, a dish made from egg and mashed potato topped with breadcrumbs and fried.
Day 2 Palermo: Half-Day Private Tour of Palermo
Today you’ll get to know Palermo in-depth alongside your own private guide. Evidence of its 3,000-year history will be revealed in the architecture and you’ll hear the stories behind the impressive buildings as well. Discover the traditional Old Quarter, including the baroque square, Quattro Canti which translates to Four Corners. It includes four buildings with baroque-style sculptures that depict the four seasons, Spanish kings, and patron saints of the old quarters. You’ll get to marvel at the various architectural styles of the 12th-century cathedral which includes a renaissance clock tower and Moorish-influenced exterior. A visit to the nearby Cathedral of Monreale is included too. One of the finest examples of Norman architecture still standing today, it dates back to the 12th century with construction started in 1174.
Day 3 Realmonte: Private Transfer from Palermo to Realmonte
After breakfast, your private driver will meet you at your hotel for a transfer to Realmonte, about a two-hour drive south. Relax and enjoy the scenery along the way. Upon arrival, you’ll check into your elegant boutique hotel where you can gaze out at the surrounding vineyards all the way down to the nearby coast. After getting settled in, you might enjoy the facilities which include a swimming pool, perfect for a refreshing dip, or to lounge around with a good book. The on-site restaurant is an outstanding place for a bite, serving traditional Italian fare, or simply unwind with a glass of wine. Tomorrow will include plenty of exploring, making the rest of the day an ideal opportunity for relaxing and soaking up the ambiance of the area.
Day 4 Realmonte: Half-Day Tour Valley of the Temples & Kolymbetra Gardens
Today your private driver will pick you up for a tour that you’ll definitely want your camera for. You’ll head to the Valley of the Temples and Kolymbetra Gardens just outside Agrigento. Marvel at the largest Doric temple ever discovered among the impressive collection of 5th-century BC Doric temples which provide a fabulous photo-op facing the sea from atop a ridge. You’ll see an unfinished Temple of Zeus and impeccably preserved temples honoring the goddesses Juno Lacinia and Concordia, nestled among almond and olive trees. The Garden of Kolymbetra, a “hidden” garden that’s been linked to the Garden of Eden in some historical texts, is an oasis between sandstone cliffs that descend to a river valley. The microclimate is ideal for the citrus, pomegranate, and olive trees that thrive here while providing a lush and fragrant scene to those who visit.
Day 5 Realmonte: Rural Sicily Food Tour with Lunch
An ideal tour for foodies, enjoy a private excursion to a local artisanal cheese farmhouse where you’ll experience the entire process of cheesemaking followed by a lunch that includes fresh farm products. Your visit includes a tour of the farm and its garden, fruit processing area, dairy, and stables with farm animals. In the didactic lab, La via del Latte, you’ll see how the milk ultimate becomes the finished product. Experience the process of pasta filata making and how one of Italy’s more unusual cheeses, Ainuzzi is made too. A stretched-curd cheese that’s modeled into the shape of animals like goats, rabbits, horses, and deer, this long-time tradition is passed down through generations of families, exclusively in the Agrigento region of Sicily. After your farm tour, enjoy a light lunch of cheese and other farm products, fruit, grilled vegetables or meat, cannoli with ricotta, and local wine.
Day 6 Siracusa: Private Transfer from Realmonte
Leaving Realmonte for Siracusa this morning, your private driver will transfer you to your hotel along the waterfront of Ortigia, Siracusa’s historic center. The city was built on an ancient Greek settlement dating back to the 8th-century BC and hosts a vast archaeological site. It features many well-preserved Greek and Roman remains, including a 5th-century BC Greek theater that once sat 15,000. After getting settled in, you might enjoy a preview of the city. Several top attractions are easily reached on foot within a 5- to 10-minute walk like the Temple of Apollo, the Fountain of Arethusa, and Piazza Duomo which holds the Cathedral of Syracuse. There are plenty of restaurants in the area while the photogenic Lungomare di Levante the hotel sits along offers a perfect vantage point for taking in a colorful sunset.
Day 7 Siracusa: Half-Day Private Syracuse & Ortigia Island Walking Tour
Discover the best of Ortigia Island and the historical center of Syracuse on this half-day private tour. Your local guide will provide insight into the history and legends behind landmarks as you stroll the narrow, colorful streets with baroque-style buildings and balconies splashed with vibrant colors. Some of the stops may include the Jewish district, Duomo, and Apollo Temple, the largest Doric temple in Sicily. Hear the story of the nymph at the Fountain of Arethusa and enjoy one of the best viewpoints of Maniace Castle which guards the island. The citadel/castle sits at the far point of the island promontory and was built between 1232 and 1240. The excursion features centuries of Sicilian history and traditions with plenty of “secrets” revealed along the way.
Day 8 Taormina: Private Transfer from Siracusa
Today you’ll head to the final destination on your itinerary, taking a private transfer from Siracusa to Taormina, about 75 miles north. This hilltop town has a history dating back to the 3rd-century BC and offers plenty of fascinating sites to explore. Ever since it was mentioned in Goethe’s Italian Journey, it’s drawn countless visitors with everything from a remarkable Greek theater to dazzling views. After checking into your hotel and getting settled in, we recommend a walk along Corso Umberto, the pedestrian street with its many upscale boutiques leading to the city’s nickname, “Sicilian Saint Tropez.” If you want to take in the best view around, head to the Greco Roman theater that overlooks the sea out to Mount Etna. You’ll find plenty of enticing eateries with outdoor patios along the waterfront for dining with a sea view too.
Day 9 Taormina: Walking Tour of Taormina
Meet our local guide at your hotel to get an in-depth look at the historic center of Taormina on a walking tour, exploring elegant squares and wandering through narrow alleyways. Visit Piazza Duomo with its magnificent baroque-style fountain and cathedral. The stone-built Duomo has a gothic interior with a fortress-like appearance and dates back to the 13th-century when it was built on the ruins of a church dedicated to St. Nicholas of Bari. It was rebuilt multiple times, in the 15th, 16th, and 18th centuries. Marvel at the 10th-century Corvaja Palace with its Arabic influence and the more than 2,000-year-old Roman Odeon, a small theater where the Roman elite enjoyed a variety of performances. The highlight is the ancient Greco-Roman amphitheater. The 3rd-century BC ruins are what the city is most well known for, complete with impeccably well-preserved original walls behind the stage area.
Day 10 Taormina: Small Group Michelin-Star Cooking Class
While delicious cuisine can be enjoyed throughout Italy with its rich diversity of regional cooking styles, Sicily is a definite standout. For those who want to share some of its mouthwatering dishes with friends or family back home, this cooking class is a must. A small-group class for up to just eight participants, it’s led by a Michelin-starred Sicilian chef. You’ll head into the cooking lab in the heart of Taormina where the chef will demonstrate the best techniques for preparing Sicilian dishes. Using your new knowledge along with your own unique and creative twists, you can play chef for the day, with assistance there when you need it. Afterward, you’ll be able to sit down to enjoy the lunch you helped make with a refreshing beverage.
Day 11 Taormina: Departure
After an enchanting 10 nights discovering Sicily in style, your adventure comes to an end. Get your bags packed and ready as your driver will meet you at your hotel this morning for a private transfer to Catania Airport, about 30 miles away. If you aren’t ready to leave just yet, reach out to your travel experts who can create a bespoke addition to your itinerary. Otherwise, with so many alluring destinations across the globe, we hope to see you again on another unforgettable getaway.
What's not Included
- As we have clients from all over the world. Our itineraries do not include flights. If you would like us to include flights in your trip, we are happy to do so. Please speak to your travel specialist at the planning stage to include them.
- Gratuities for local guides
- We strongly advise all guests purchase comprehensive travel insurance
- Visas if required
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