Sicily is one of the most fascinating regions in Italy. At the center of the Mediterranean, it has seen trade and cultural exchange for millennia. From the ancient Greeks who built amphitheaters and cities you can still visit today, to the Arabs who shaped Sicilian cuisine with citrus, nuts and spices, to the Normans who built the island’s majestic cathedrals — the layers of history here are unlike anywhere else in the country.
I’ve been a dozen times over the past decade and there’s always something more. I generally recommend focusing on either the eastern or western side of the island (each has a distinct personality), but sometimes you want a real overview. This itinerary covers both in 10 days at a pace that’s full without being frantic. If you have 14 days, you can slow down and add a stop or two along the way.
Taormina
Fly into Catania and pick up a rental car before heading north to Taormina. Catania is a fascinating city with a raw, volcanic energy that recalls Naples, my favorite place in Italy—but if this is your first time and you’re short on time, save it for another trip.
Taormina is often called the prettiest town in Italy, which comes with the prices and crowds to match. It has a Positano-like atmosphere, but set high above the Ionian Sea with Mount Etna on the horizon.
The Teatro Antico is undoubtedly one of the most photogenic Greek theaters in existence — built in the 3rd century BC, it was designed to frame Etna as a backdrop, which means the stage set hasn’t changed in two thousand years. Don’t miss Casa Cuseni, an Arts and Crafts villa that doubled as a salon for the likes of Roald Dahl and Bertrand Russell, now open as a small museum and hotel. Discover more tips in our Taormina Travel Guide.
Where To Stay
If you prefer to be close to the water and plan to spend time at the beach, stay at sea level rather than in town — the funicular connects the two. You can opt for Mazzarò Sea Palace for a splurge or La Plage Resort for something more affordable. However, we’d recommend staying in the centro of Taormina town for the full experience. Hotel Villa Schuler has a great position in town, just a short walk to the Teatro Antico, or relive your White Lotus dreams at the the Four Seasons San Domenico Palace.
Adding Mount Etna: If you have an extra night (or two), I’d carve them out for Etna before or after Taormina. Europe’s most active volcano is also one of its most exciting wine regions, with mineral-rich soils producing increasingly sought-after Nerello Mascalese reds. Staying at one of the boutique wine estates on the mountain is an experience in itself — we’ve covered our favorite places to stay in our Mount Etna Hotels Guide.
Ortigia, Syracuse
From Taormina, drive south into the Val di Noto — the Noto Valley — a stretch of Sicily’s southeastern corner that is home to a cluster of opulent, Baroque towns.
After a devastating earthquake in 1693 leveled most of the region’s towns, they were rebuilt almost simultaneously in the ornate, theatrical Baroque style of the moment. The result is a cluster of honey-stone cities that feel like open-air stage sets: Noto, Ragusa, Modica, Scicli, and most beautiful of all, Ortigia. You could spend a whole week just exploring this one area, but for the sake of this road trip, we’re dedicating two nights here.
Ortigia is the ancient island heart of Syracuse, connected to the mainland by a short bridge but feeling completely apart from it. Syracuse was one of the great cities of the ancient world — at its peak in the 5th century BC, it rivaled Athens in wealth and influence.
Today, Ortigia is an atmospheric town filled with excellent restaurants, artisanal boutiques, aperitivo bars and sea breezes from every direction. It doesn’t have proper beaches — there are rocky platforms and a small cove for swimming — but you can drive to nearby beaches in under 20 minutes. Spend your evenings over wine and pasta in the narrow backstreets, and your mornings at the Mercato di Ortigia. See more tips in our Ortigia Travel Guide.
Where To Stay
Need to rewrite this section. Stay within the island of Ortigia itself — just confirm parking arrangements when you book, as much of the centro is pedestrian-only. Palazzo Lume is my recommendation: a quietly beautiful boutique hotel housed in a restored noble palazzo, with just a handful of rooms, carefully curated interiors and the kind of calm that feels earned after a day of sightseeing.
If you have extra days: Add 1-2 nights at Relais Antica Badia in Ragusa or Casa Talia in Modica — both are stunning Baroque towns and worth a dedicated stay.
En route: Noto
On the way from Ortigia to Vittoria, stop for a walk through Noto, the town that lent its name to the valley. Two hours is plenty: stroll down Corso Vittorio Emanuele III, admire the amber facades of the Baroque churches bathed in afternoon light, and stop at Caffè Sicilia for one of the finest cassatas on the island.
Vittoria
Vittoria is a town most travelers skip, which is a shame if you love wine. It’s home to Cerasuolo di Vittoria, Sicily’s only DOCG — the highest classification in Italian wine. A blend of Frappato and Nero d’Avola, it’s aromatic, food-friendly and surprisingly elegant. The estates to visit are Arianna Occhipinti, who launched her winery at 22 and has become one of Italy’s most respected natural winemakers, and COS (co-founded by Giambattista Cilia and Giusto Occhipinti), which produces wines in clay amphorae following ancient Greek methods. Both are open for visits.
Where To Stay
Baglio Occhipinti is a historic Sicilian baglio — a fortified farmhouse built around a central courtyard, once the heart of rural life in this part of the island — now transformed into a boutique hotel of twelve suites by Fausta Occhipinti, Arianna’s sister and a talented architecture and landscape designer.
The result feels both deeply rooted and quietly refined. Fausta has furnished every room with handpicked pieces — antiques, artisanal textiles, locally crafted ceramics — and the suites open onto gardens planted with native species, lavender and citrus trees. The saltwater swimming pool overlooks the open countryside, and you can enjoy bike rides through the countryside and picnics in the garden. Breakfast is laid out each morning like a small ceremony: local cheeses, fruit from the garden, Sicilian pastries. Dinner follows a daily changing menu built around what the land and season offer.
En route: Villa Romana del Casale in Piazza Armerina
From Vittoria, drive inland to Villa Romana del Casale in Piazza Armerina (about 90 minutes). This 4th-century AD hunting villa contains the most extensive Roman floor mosaics in the world. The scenes range from mythological sea battles to exotic animals being loaded onto ships, to the famous “Bikini Girls” — ten women competing in athletic games in unmistakably ancient two-pieces. After your visit (about 2 hours), grab a bite at the snack shops near the parking lot before moving on.
Discover more Heritage Sites In Sicily You Can’t Miss.
Agrigento
Then continue to Agrigento (another 90 minutes), an arid, wind-swept coastal city home to the Valley of the Temples — five Greek temples from the 5th century BC and among the best preserved in the world. At its peak, ancient Agrigento rivaled Athens and Carthage in size. The Temple of Concordia is the highlight, its Doric columns nearly complete thanks to its conversion into a Christian church in the 6th century AD. Park at the Porta V lot, take a taxi to the Tempio di Giunone entrance and walk downhill from there.
Worth a stop: afterward, head to Scala dei Turchi — a white marl cliff shaped by wind and sea into a natural staircase above the water. The best view is from the Belvedere, and you should also descend to the beach at Lounge Beach Scala dei Turchi for a swim and lunch before heading to your hotel for the night.
Where To Stay
Villa Athena, an 18th-century villa set directly inside the archaeological park, with the Temple of Concordia illuminated outside your window at night. Book a room facing the temple and walk among the ruins at dusk, after the crowds have gone.
Palermo
The last stop on this itinerary is the riveting city of Palermo — beautiful chaos, opulent decadenza, timeworn architecture and deeply cherished traditions. Palermo was the seat of the Arab-Norman kingdom and this history is reflected everywhere: in the Islamic-style architecture of the Cappella Palatina and the Church of San Giovanni degli Eremiti, with its iconic red domes, and in the Cathedral, which has been a Byzantine church, a mosque and a Norman basilica at different points in its history.
Beyond the monuments, the Ballarò market is essential — one of the oldest street markets in Europe, trading since the Arab period, with an atmosphere that hasn’t changed much. Go in the morning for the full experience: fresh fish, grilling street food, blood oranges piled high on wooden crates.
You must also walk to the Quattro Canti, a Baroque piazza with four ornate carved façades, and Piazza Pretoria, which contains an enormous, flamboyant Renaissance fountain nicknamed the Fountain of Shame by scandalized residents when it arrived in the 16th century — all those nude figures. A must-see is Santa Caterina, a church and former nunnery with a (no longer so secret) pastry shop inside and beautiful views from the rooftop. See more tips in our Palermo Travel Guide.
Where To Stay
In a city this boisterous, Palazzo Balsamo feels like a welcome respite. Tucked along one of the narrow alleyways surrounding the Ballarò market — this 19th-century noble residence has been transformed into a boutique hotel with soft curves, shell-shaped furniture and walls finished in warm natural clay.
The 16 rooms are all different, with cloud-like beds by Italian atelier Bolzan, travertine bedside tables and pastel linens. Some have freestanding bathtubs; the living suite opens onto balconies over the rooftops of Via Maqueda.
For years the palazzo housed a bicycle repair shop. That space is now the Atelier del Barone, the hotel’s chic all-day lounge where breakfast is overseen by Michelin-starred chef Giuseppe Costa. Beyond the buffet, there’s an à la carte menu with options like a poached egg on pumpkin consommé or pancakes with Sicilian mango purée.
Discover more great places to stay in our Palermo Hotel Guide.
If you have more time
On your final morning, drive to the Palermo airport to fly home. However, if you have more time, there are plenty of destinations you can add-on to your trip.
Head east to Cefalù for two nights of sea and sunshine along Sicily’s northern coast. The Norman cathedral there contains some of the finest Byzantine mosaics in Italy and the town itself is beautifully preserved. This is one of the best beach towns in Sicily, if not all of Italy. See our Cefalù Travel Guide.
Head west to explore Trapani, the clifftop medieval town of Erice, and the Egadi Islands — three small islands off Sicily’s western tip with clear water, little tourism and a fascinating tuna fishing history that dates back thousands of years. The pretty fishing village of Scopello is nearby, as is the Riserva dello Zingaro, a protected coastal nature reserve with hiking trails above a series of secluded beaches.
The Aeolian Islands are a highlight of any extended Sicily trip and deserve at least 1-2 weeks on their own. Reach them from Catania by driving north to Milazzo and taking the ferry. See our Aeolian Islands Travel Guide and Aeolian Islands Hotel Guide for more tips.
Practical Notes
Getting around: A rental car is essential for this itinerary. Book in advance through a major agency (we recommend Sixt), request an automatic transmission and take full insurance coverage. Roads are generally good but narrow in historic centers — don’t assume you’ll be able to park directly in town.
Parking: Parking can be inconsistent and poorly marked, especially in historic centers. Blue lines generally indicate paid parking, but meters aren’t always obvious or intuitive. Download EasyPark in advance — it works across much of Sicily and saves time (and guesswork) when you arrive. Be mindful when parking in more isolated areas: avoid leaving suitcases or visible valuables in the car, particularly at beach access points or trailheads. It’s not a major issue, but a bit of awareness goes a long way.
Cash: While most hotels and restaurants accept cards, smaller trattorias, beach clubs and cafés still often prefer cash, particularly outside major cities. Always carry some euros with you to avoid awkward moments.
What to wear: Sicily rewards a bit of effort, but practicality matters more. Bring comfortable shoes with grip — you’ll be walking on uneven stone streets and climbing more stairs than you expect, especially in the Baroque towns of the Val di Noto. Even short distances can involve steep inclines.
Best time to go: April through June, and September through early November. July and August are peak season: hot, crowded and expensive, particularly in Taormina and Agrigento. Spring offers wildflowers in the Valley of the Temples and ideal driving conditions. Autumn brings the grape harvest in Vittoria and a more local atmosphere throughout.
Planning a trip to Sicily? You might also like:
- How To Spend A Weekend In Taormina
- How To Spend A Weekend In Palermo
- The Best Boutique Hotels In Palermo
- How To Spend A Weekend in Cefalù
- How To Spend A Weekend In Ortigia, Syracuse
- The Best Hotels On Mount Etna
- Aeolian Island Travel Guide
- The Best Hotels On The Aeolian Islands
- A Complete Guide To Sicilian Food
- 7 Heritage Sites In Sicily You Can’t Miss
- A Love Letter To Scopello
