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Sicily Itinerary: 5 Days Through Taormina & Palermo
5 Days
2 Stops
Private transfer
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Trip curated by Roman Karin
ExpertMy team and I crafted this trip! Want to make it even more your style? Let’s chat — you can book a free planning call with me.
My team and I crafted this trip! Want to make it even more your style? Let’s chat — you can book a free planning call with me.
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Taormina
Day 1 - 2
Taormina enjoys an idyllic location, favourably perched on a steep mountainside with panoramic views of Mount Etna, two grand sweeping bays and a picturesque Graeco-Roman amphitheatre. Drenched in sunshine year-round, this chic resort town attracts a steady stream of celebrities and holidaying high-rollers. Despite its unashamedly touristy atmosphere, its natural beauty is undeniable. The town’s chaotic network of winding streets is strewn with luxury designer boutiques, ancient churches and flower-filled balconies adorning beautifully restored medieval buildings and intimate piazzas. Taormina is especially magnificent on clear days when you can view the exquisite flora and flora against a backdrop of snow-capped volcanoes spewing puffs of white smoke into a mesmerizingly blue sky. Make sure to spend an afternoon picnicking in the gorgeous Giovanni Colonna Park.
NH Collection Taormina
The NH Collection Taormina hotel is located in the city center of Taormina with convenient access to the Duomo di Taormina and the Isola Bella. You'll find sophisticated rooms and suites which feature bathtubs, free internet access, digital safes, hairdryers, slippers, and NH Collection bathroom amenities. Dining options include Zefiro Restaurant and Lu Souli Bar and Restaurant which serves light dishes and typical Sicilian street food. You can enjoy workouts in the fitness center and a post-workout relaxing dip in the swimming pool. The roof terrace is ideal for quiet reading or intimate conversations. Other refreshing amenities include a spa, sauna, solarium, and steam bath.
Your activity
Etna Half Day Tour
Enjoy a morning tour to Mount Etna, the highest active volcano in Europe. Driving through some of the quaintest villages placed on the slopes of the volcano, you will reach 1,986 meters where you will be able to visit the Sylvester Craters. Afterwards, you will return to Taormina. Mount Etna is one of the most active volcanoes in the world and is in an almost constant state of activity. The fertile volcanic soils support extensive agriculture, with vineyards and orchards spread across the lower slopes of the mountain and the broad Plain of Catania to the south. Due to its history of recent activity and nearby population, Mount Etna has been designated a Decade Volcano by the United Nations. You have the option to take the cable car from 1,986 to 2,500 meters for further exploration of the volcano's higher regions.
Palermo
Day 3 - 5
Palermo lies on the northern coast of the Italian island of Sicily. The Sicilian capital, this ancient city – about 2700 years old – boasts numerous cultural and historical sights. Begin with the UNSECO listed sites, including the Palazzo Reale and churches such as the 12th-century San Giovanni degli Eremiti (with Arabic influences; and cultural treasures such as the 19th-century Teatro Massimo and the UNESCO-listed tradition of Puppet Theatre (performed through-out the city) and detailed in the Museo delle Marionette. Then head to religious sites including the Palermo Cathedral with a 12th-century mausoleum and explore unique attractions such as the macabre Catacombe dei Cappuccini – a cemetery holding mummified corpses (some dating from the 16th-century). Finally, visit markets, artisanal eateries and bars in town, while there are numerous near-lying sights, for fantastic day-trips from the city.
Grand Hotel Et Des Palmes
The Grand Hotel Et Des Palmes is located in the heart of Palermo's old town. From here you can easily reach sights such as the famous Cathedral of Santa Maria Assunta, the Capella Palatina, the Teatro Massimo and San Giovanni Degli Eremiti. The accommodation consists of rooms, each equipped with air conditioning, a private bathroom, a safe, a hairdryer, a minibar, a satellite TV and a direct dial telephone. A delicious buffet breakfast is served each morning. Further amenities include Internet access and a roof terrace.
Your activity
Walking Tour of Palermo
Discover the soul of Sicily with a captivating morning walking tour through the historic streets of Palermo. Stroll past architectural gems such as the Quattro Canti, a stunning example of Spanish Baroque style, and admire the majestic Norman Palace. Step inside the Palatine Chapel, a masterpiece of Arab-Norman art, and explore the imposing Cathedral of Palermo, where history and grandeur come together. Continue to the lively Capo Market, one of the oldest and most vibrant street markets in the city, where colors, aromas, and voices tell the true story of Palermo. Pick-up included is only for hotels located in the historic city center.
From$4,800
per personAccommodations
Transportation
24/7 support
Activities
Tourlane App
Travel plan
Flights
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Why plan with an expert?
200+
Plan with professionals who are explorers themselves.
17+ hours of time saved
Our experts plan and book for you.
8+ Bookings managed
Everything is bundled in one place and perfectly planned.
5+ Transfers coordinated
For optimal transport and comfort.
Excellent
Itinerary inspiration
Explore the best of Sicily in just five days with this thoughtfully curated 5-day itinerary that blends ancient wonders, natural beauty, and rich island culture. Start your journey in Taormina, where sweeping views of the Ionian Sea and Mount Etna set the scene. Stroll through elegant streets, visit historic landmarks, and experience the relaxed rhythm of this hilltop town. Continue your exploration with excursions that reveal Sicily’s dramatic landscapes and deep-rooted history, from volcanic terrain to ancient cities shaped by Greek and Roman influences.
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Your journey then leads to Palermo, a vibrant city full of contrasts, where bustling markets, ornate architecture, and diverse cultural influences come together. Along the way, discover UNESCO-listed sites, sample regional specialties, and explore some of Sicily’s most remarkable archaeological treasures. With private transfers, guided experiences, and carefully selected accommodations, this itinerary offers a seamless and enriching introduction to Sicily’s most iconic highlights.
Day 1–3: Taormina (3 Nights)
Perched high above the sea, Taormina combines natural beauty with historic charm. Its panoramic views, ancient landmarks, and relaxed atmosphere make it one of Sicily’s most captivating destinations.
Your Accommodation
NH Collection Taormina
Highlights & Activities
Private transfer upon arrival
Explore Taormina and the Greek Theatre
Half-day excursion to Mount Etna
Full-day trip to Syracuse
Day 4–5: Palermo (2 Nights)
Palermo offers a vibrant mix of cultures, shaped by centuries of influences. From lively markets to grand churches, the city reveals Sicily’s diverse heritage at every turn.
Your Accommodation
Grand Hotel Et Des Palmes
Highlights & Activities
Private transfer to Palermo
Palermo and Monreale full-day excursion
Day trip to Agrigento and Piazza Armerina
Day 6: Departure
Private transfer to the airport
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Tips for your 5-day Sicily itinerary
April–June and September–October are the most pleasant months. These seasons offer warm but comfortable weather for exploring Taormina’s Greek Theatre, walking Palermo’s markets, and visiting archaeological sites like the Valley of the Temples.
On average, travelers spend about $190 per person per day, excluding flights. Budget trips start around $60/day with simple hotels and local food, while luxury options reach $330/day for boutique hotels, fine dining, and private tours. Hotels range from about $50 per night for 1–2 star stays to $110+ for higher categories. Meals are $9–$13 in snack bars, $16–$28 in casual restaurants, and $45–$80 for a three-course dinner. Excursions like Mount Etna tours cost around $90–$120.
Taormina’s Greek Theatre with Mount Etna views, Palermo’s Palatine Chapel, and Syracuse’s archaeological park are key highlights. The Valley of the Temples in Agrigento and the mosaics of Piazza Armerina also stand out. Activities like wine tastings, guided food tours, and full-day excursions to Etna or Monreale enrich the trip.
Book tickets early for major sites such as the Palatine Chapel or Valley of the Temples. In Taormina, mornings are best to avoid crowds. Renting a car makes day trips flexible, but buses and trains are affordable for longer connections, such as Palermo to Catania.
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