Italy Unveiled: The Ultimate Sicily Trip Itinerary

Arrive at Palermo Airport (PMO) and prepare for an enriching stay in Palermo, where two to three nights are recommended to fully explore its treasures. If you land early in the day, a two-night stay should suffice. Driving in Palermo can be quite the adventure—locals have their own unique driving style that might catch you off guard if you're not used to it. I highly recommend not driving yourself in Palermo. Hire a driver or take taxis.

Day 1: A private guided tour where you can fully immerse yourself in the city's charm is the ideal way to see the city. From the grandeur of the Teatro Massimo Theater to the intricate beauty of the Palatine Chapel, there's so much to take in. And with a guide leading the way, you won't miss a beat. No need to constantly glance at your phone's map—you'll be too busy admiring the ancient marvels around you. Plus, the stories and insights shared by your guide will make the experience even more captivating. I advise to take your tour the first day. It's the perfect introduction to Palermo, setting the stage for more explorations in the days ahead.

On day two, delve deeper into the sites that caught your eye during your tour, indulging in a leisurely exploration of Palermo's hidden gems. Treat yourself to a traditional Italian lunch at a charming sidewalk restaurant, where you can savor the flavors of authentic pizza and wine while soaking in the lively atmosphere.

For dinner, why not immerse yourself in local hospitality by dining at a Sicilian's home? Sicilians are renowned for their warmth and hospitality, offering various opportunities to experience homemade Sicilian cuisine in a cozy, familial setting. It's an unparalleled chance to forge new connections and create lasting memories in this enchanting land.

Day three: Departing from Palermo, you'll journey southwestward towards a charming coastal retreat. Along the way, make a stop at The Cathedral in Monreale, a breathtaking architectural marvel constructed between 1170 and 1189, now listed as a UNESCO World Heritage site. Opting for a guided tour of the Cathedral allows you to delve into its rich history and appreciate the intricate artwork adorning its interiors.

Your next destination is Verdura Resort, a luxurious Rocco Forte Hotel nestled between Palermo and the renowned Valley of the Temples. I suggest a two-night stay at this beachfront oasis. With its expansive 600-acre estate, Verdura Resort provides a plethora of recreational activities including three golf courses, tennis courts, basketball facilities, and a range of water sports. Moreover, the resort cultivates its own oranges and olives, which are ingeniously incorporated into their culinary offerings. For ultimate relaxation, indulge in the spa's extensive amenities spanning over 4,000 square feet, featuring a hydrotherapy circuit, Turkish bath, hair salon, and eleven treatment rooms. Take advantage of this wonderful opportunity to rejuvenate before your itinerary picks up pace once more. Afterall, a vacation should include some R&R as well.

Day four: Spend an entire day enjoying the resort and beach. Be sure to watch the sunset from their rooftop bar.

Day five: Begin your morning with an early departure from Verdura Resort to beat the crowds and journey towards the awe-inspiring Valley of the Temples, situated approximately an hour from the resort.

This renowned archaeological site is best explored with the guidance of a knowledgeable expert to truly grasp its historical significance. Plan to dedicate about two hours to fully immerse yourself in its wonders.

Afterwards, spend the rest of the afternoon soaking in the sights and sounds of Agrigento before settling into Hotel Villa Athena for an unforgettable overnight stay. Treat yourself to a room boasting stunning views at this esteemed hotel, conveniently located within walking distance of the temple. For dinner, indulge in the delectable cuisine served at the hotel's restaurant, where you can enjoy a meal while marveling at the enchanting sight of the illuminated temple in the evening.

Day six: Set off on a scenic drive to Taormina, your home for the next four nights. Enjoy a two-night stay at either the Four Seasons or the Grand Hotel Timeo, A Belmond Hotel, Taormina, both ideally situated in town, granting easy access to numerous historical sites, shopping areas, and dining spots. The journey from The Valley of the Temples to Taormina takes approximately two-and-a-half hours, so take your time and plan to arrive in the late afternoon.

Upon arrival, check in to your accommodation and then take a leisurely stroll through town to stretch your legs and explore the local shops. Don't miss the opportunity to peruse the custom sandal options available in town—several stores offer the chance to select the color and style of the sandal top, with the artisans crafting your personalized sandals right on the spot.

Day seven: Begin your day with an early morning tour of Taormina, aiming for a start time around 8:30 a.m. for the best experience. Taormina tends to get quite crowded later in the day, especially on cruise port days, so it's wise to plan your visit accordingly. Your knowledgeable guide will provide insights into the city's history, its origins, and its evolution, while also highlighting some local gems. Be sure to explore the Ancient Theater of Taormina, conveniently located adjacent to the Grand Hotel Timeo. In the afternoon, unwind and soak up the sun by the pool at your historic hotel, reveling in the breathtaking views offered by these remarkable resorts. It's the perfect opportunity to relax and recharge amidst the beauty of Taormina.

Day eight: Transition to your new accommodation at Villa Sant 'Andrea, A Belmond Hotel, Taormina Mare, just a short 15-minute drive away and nestled along the coast. This change in scenery will allow you to continue exploring the area while escaping the crowds of Taormina, offering you the best of both worlds. Villa Sant 'Andrea boasts a prime location on a private beach, providing unforgettable views of the coastline.

After check-in, take a guided tour of Mount Etna, Europe's most active volcano, which offers a range of fascinating options. For an adventurous experience, consider the off-road tour, which takes you to the site where their ski chalet was engulfed by a lava eruption—you can still catch a glimpse of the ski lodge peeking out from the cooled lava rock. Afterwards, indulge in a delightful lunch at Santa Maria La Nave winery, where you'll be treated to a magical culinary experience amidst the stunning surroundings. Etna's unique landscape, shaped by its volcanic activity, makes wine production here particularly thrilling.

The Santa Maria winery takes pride in crafting their cuisine from scratch, even sourcing grains from a local farmer—an experience not to be missed during your visit. Conclude your day with a delectable dinner at Villa Sant 'Andrea, accompanied by exceptional views of the harbor, ensuring a memorable end to your day of exploration.

Day nine: Enjoy a leisurely day at Villa Sant 'Andrea's beach club—it's an experience that's truly enchanting!

Day 10: Journey approximately an hour to Catania, where your departure from CTA Airport awaits. If your flight is scheduled for the evening, take advantage of the day to explore the town. Wander into the vibrant atmosphere of Catania by visiting its renowned fish market and exploring the myriad street markets tucked away in the quaint alleyways and side streets.