The Ultimate 10-Day Sicily Itinerary

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This 10-day Sicily itinerary is ideal for first-time visitors, blending iconic sites with luxury stays, private transfers, and island escapes.

Sicily is one of Italy's most enchanting destinations-an island where fiery volcanoes meet sparkling seas, ancient Greek temples rise above citrus groves, and medieval cities buzz with life. For first-time visitors, planning the perfect route can feel overwhelming. That's why this curated 10-day luxury Sicily itinerary blends the island's can't-miss highlights with seamless travel days, iconic hotels, and authentic local experiences.

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Why This Itinerary Is Perfect for First-Time Visitors

This itinerary is perfect for first-time visitors to Sicily, guiding you through the island's greatest highlights-from the cliffside beauty and ancient theater of Taormina to the volcanic landscapes of the Aeolian Islands, the charming medieval streets and beaches of Cefalù, and the vibrant history, markets, and architecture of Palermo.

Distances are easy to manage with smooth connections, and each hotel has been carefully selected for luxury, comfort, and prime location. By balancing sightseeing with ample relaxation, this plan offers an ideal introduction to all that Sicily has to offer.

Day 1: Day 1: Arrive in Catania → Private Transfer to Taormina

Your Sicilian adventure begins as soon as you land at Catania-Fontanarossa Airport (CTA). After collecting your luggage, your private driver will meet you and escort you north along the dramatic Ionian coastline. Within 45 minutes, the scenery shifts from lava stone villages to Taormina's glamorous clifftops.

Check-In: Mazzarò Sea Palace

Mazzarò Sea Palace is a luxurious beachfront retreat set directly on one of Taormina's most beautiful coves, offering a true "feet-in-the-sand" Sicilian escape. With spacious sea-facing rooms and private terraces overlooking the bay, the hotel blends coastal elegance with effortless relaxation.

Guests can unwind at the panoramic pool, enjoy refined Mediterranean dining, or take the cable car just steps away to reach Taormina's historic center in minutes. Ideal for honeymooners and beach lovers, it's a serene hideaway with postcard-perfect views at every turn.

Located directly on the bay, this 5-star hotel offers:

  • Spacious sea-view suites
  • A serene private beach
  • A panoramic pool deck
  • Boat access for coastal tours
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Afternoon in Taormina

Settle in with a refreshing spritz by the pool or lounge on the private beach surrounded by crystal water.

Take the cable car up to Taormina town, where winding alleyways, bougainvillea balconies, and charming piazzas set the tone for your trip.

Dinner Suggestions

  • Il Barcaiolo - intimate seafood restaurant right on the water
  • Anciovi - fresh, modern Sicilian flavors with sea views

End your night with gelato from Bam Bar, the local favorite.

Day 2: Explore Taormina's Iconic Beauty

Taormina is often the highlight of Sicily for first-timers, combining history, shopping, scenery, beaches, and culture.

Must-See Highlights:

  • Visit the Ancient Greek Theatre for iconic views of the coastline.
  • Stroll Corso Umberto, exploring shops and gelaterias.
  • Take a boat tour to Isola Bella, swimming in turquoise coves.
  • Optional: Wine tasting on Mount Etna or a private cooking class.

Dinner at Metropole or Casa Niclodi sets the perfect end to the day.

Day 3: Taormina → Milazzo → Ferry to Vulcano

After breakfast at the hotel, take a private transfer to Milazzo Port (about 1 hour 20 minutes), where you'll board a hydrofoil to the Aeolian Islands. The ride to Vulcano takes about 50 minutes, offering beautiful views of the islands rising from the sea.

Check-In: Therasia Resort & Spa

Perched on the cliff-top of the promontory of Vulcanello on Vulcano (in the Aeolian Islands), Therasia Resort Sea & Spa offers breathtaking views over the Tyrrhenian Sea and neighboring islands. The resort blends Mediterranean architecture and natural materials - lava stone, Sicilian terracotta, cedar and olive-wood furnishings - with bright, airy rooms and terraces, many with sea views.

Guests can relax in two infinity pools that seem to merge into the horizon, swim from a private rocky platform, or indulge in the full-service spa with thermal treatments, Turkish bath, sauna and hydro-massage pool.

Dining is a highlight: the resort features several restaurants including the Michelin-starred "Il Cappero" plus vegetarian-friendly fine dining, all serving fresh Sicilian cuisine. With its tranquil setting, luxurious amenities, and nature all around, Therasia is ideal for travelers seeking a peaceful, upscale island escape.

One of Sicily's most breathtaking properties, this cliffside resort offers:

  • Terraces overlooking Stromboli and Lipari
  • Infinity pools carved into the rock
  • A world-class spa
  • Three restaurants, including the Michelin-starred Il Cappero
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Afternoon Suggestions

  • Enjoy the outdoor pools overlooking the volcanic archipelago
  • Take a walk along the rugged lava-rock coastline
  • Book a sunset aperitivo on the panoramic terrace

Dinner at Il Cappero (book far in advance) makes this day unforgettable.

Day 4: Discover the Magic of Vulcano

Vulcano is raw, dramatic, and peaceful-perfect for slowing down.

Top Experiences on Vulcano:

  • Gran Cratere Hike - A manageable 1.5-2-hour hike offering astonishing views of the entire Aeolian chain. The trail winds through sulfur vents and volcanic ash.
  • Black-Sand Beaches - Vulcano's beaches are known for warm, soft black sand created by eruptions.
  • Spa Day at Therasia - Relax with volcanic mud facials, seaweed treatments, and hydrotherapy pools.
  • Private boat charter - Take a boat around Lipari, Salina, or even Stromboli for a lava-view sunset.

Dinner at Arcipelago or a return to Il Cappero rounds out a perfect evening.

Day 5: Vulcano → Milazzo → Train to Cefalù

Catch the morning ferry back to Milazzo and walk or transfer to the train station. The coastal train ride to Cefalù (approx. 1.5-2 hours) is scenic, passing beaches, vineyards, and cliffs.

Check-In: Le Calette No. 5

Le Calette No. 5 is an intimate, design-forward boutique hotel carved into the rocky coastline just outside Cefalù's old town. Sleek, contemporary suites open onto terraces with dramatic sea views, while the property's hidden coves and wooden decks create a private, resort-style atmosphere.

Guests can lounge by the infinity pool, enjoy fresh seafood at the waterfront restaurant, or hop on the complimentary shuttle to explore Cefalù's charming medieval center. Stylish, quiet, and undeniably romantic, it's one of the top coastal stays in northern Sicily.

A contemporary boutique hotel carved into the cliffs, featuring:

  • Private sun decks
  • A serene saltwater pool
  • Direct sea access
  • Shuttle service to town
BOOK NOW

Afternoon in Cefalù

Wander the cobblestone streets lined with trattorias and artisan shops, or relax on Le Calette's private beach platform.

Dinner Recommendations

  • Bastione & Costanza - seaside dining with fresh seafood
  • Il Normanno - traditional Sicilian dishes with a modern twist

Day 6: Explore Medieval Cefalù

Cefalù is a gem-half medieval village, half Mediterranean beach town.

Highlights in Cefalù:

  • Cefalù Cathedral - A UNESCO World Heritage site with golden Byzantine mosaics.
  • La Rocca Hike - A moderate climb to views across the coastline, ancient fortifications, and the Norman walls.
  • Cefalù Beach - One of Sicily's most photogenic beaches, with golden sand and a dramatic backdrop.

Insider Tips:

  • Go early to beat crowds at La Rocca.
  • For lunch, Ti Vitti in the heart of town is an excellent choice.

Enjoy a slow sunset walk by the harbor before returning to your hotel.

Day 7: Cefalù → Train to Palermo

The quick 50-minute train ride brings you to Sicily's vibrant capital: Palermo.

Check-In: Villa Igiea

Villa Igiea, a grand Rocco Forte hotel, is Palermo's crown jewel-an aristocratic 19th-century villa transformed into a five-star haven overlooking the Gulf of Palermo. Its frescoed halls, lush terraced gardens, and serene seaside pool evoke old-world glamour, while newly renovated rooms pair Sicilian craftsmanship with contemporary elegance.

Guests can savor refined dining, indulge in the Irene Forte Spa, or retreat to the iconic bar for sunset cocktails. Just minutes from Palermo's cultural landmarks yet blissfully peaceful, Villa Igiea offers the perfect blend of history, luxury, and coastal tranquility.

This Belle Époque palace is one of Italy's most iconic hotels. Expect:

  • Palatial gardens
  • A stunning sea-view pool
  • Elegant suites designed by Olga Polizzi
  • Michelin-level dining
  • Shuttle service into the historic center
BOOK NOW

Afternoon in Palermo:

  • Visit Quattro Canti, the city's symbolic crossroads
  • Wander the Baroque-filled Piazza Pretoria
  • Step inside San Cataldo & Martorana (Arab-Norman UNESCO gems)

Dinner Options:

  • Gagini - upscale Sicilian cuisine
  • Osteria dei Vespri - atmospheric dining in Piazza Croce dei Vespri

End the evening with a nightcap in Villa Igiea's historic bar.

Day 8: Palermo's Historic & Cultural Highlights

Start with a Sicilian breakfast at Villa Igiea, then head into the city.

Essential Stops:

  • Palermo Cathedral - an architectural mix of Gothic, Moorish, and Norman design
  • Palazzo dei Normanni & The Palatine Chapel - glittering Byzantine mosaics
  • Ballarò Market - sample panelle, arancini, cannoli, and fresh fruit
  • Casa Professa - one of Palermo's most ornate churches (entry €2)

Day 9: Relaxation + Last-Day Highlights

Spend your final full day savoring Palermo at your own pace.

Ideas for Your Last Day:

  • If the weather is warm: Mondello Beach (20 minutes away)
  • Lounge by Villa Igiea's pool overlooking the marina
  • Book a spa treatment at Irene Forte Spa
  • Take a Sicilian cooking class or wine tasting
  • Visit the botanical gardens

Farewell Dinner:

Osteria Mercede or Villa Igiea's Florio Restaurant are both unforgettable choices.

plane window looking onto sunset and clouds

Day 10: Depart Palermo

Your driver will take you to Palermo Airport (PMO) for your flight home. If you have time, stop for one last granita-because there's no such thing as too much Sicilian sweetness.

Ready to Book Your Luxury Fall Trip?

Want me to design a trip like this for you? Contact me today to start planning your bespoke Italian journey.

From private transfers and exclusive tours to handpicked hotels, I'll ensure every detail is perfectly tailored to your travel style.

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