Sicily is a crossroads of the Mediterranean, layered with Phoenician harbors, Greek theaters, Arab gardens, Norman palaces, and Baroque piazzas. It’s also a place of living traditions—from puppet theaters and religious festivals to open-air markets perfumed by citrus and sizzling panelle. Mount Etna, Europe’s highest active volcano, watches over it all, feeding vineyards with its mineral-rich soils.

This 5-day Sicily itinerary focuses on two essential bases: Palermo (west) and Taormina (east). You’ll nibble through legendary street food, step into golden mosaics that rival Byzantium, and stroll cliffside lanes overlooking a glittering Ionian Sea. Then you’ll head to Etna’s countryside for lava landscapes, boutique wineries, and a meal you’ll remember long after you’ve packed your bags.

Practical notes: many shops take a midday pausa (siesta), markets are liveliest in the morning, and historic centers have ZTL (limited-traffic zones)—park on the perimeter if you’re driving. Book popular experiences and restaurants in advance, carry a little cash for small bites, and come hungry—cannoli, arancini, and pistachio everything await.

Palermo

Palermo is a sensory jolt: Byzantine mosaics glint in candlelight, Arabic arches frame courtyards of orange trees, and fishmongers sing at dawn in centuries-old markets. The city’s UNESCO-listed Arab-Norman route links the Palatine Chapel’s golden stories with the sea-facing district of La Kalsa and its palazzi reborn as galleries and cafes.

• Top sights: Norman Palace & Palatine Chapel, Palermo Cathedral, Quattro Canti, Teatro Massimo, and the markets of Capo, Vucciria, and Ballarò.
• Food to try: panelle (chickpea fritters), sfincione (Sicilian pizza), arancini, stigghiola, and “brioche col gelato.”
• Neighborhood vibes: Centro Storico for spectacle, La Kalsa for creative energy, Politeama/Libertà for a calmer, elegant stay.

Where to stay: Search stays near Quattro Canti or Politeama for easy walking to markets and monuments. Browse options here: Palermo hotels on Hotels.com and Palermo vacation rentals on VRBO.

How to get to Palermo: Fly into PMO. For flights from within Europe, compare on Omio (flights). For long-haul and non-Europe routes, use Trip.com (flights). Overland travelers can check trains/ferries through mainland Italy on Omio (trains).

Day 1: Arrive in Palermo (afternoon arrival)

Afternoon: Check in and stretch your legs along Via Maqueda to Quattro Canti, then into Piazza Pretoria with its baroque fountain. Duck into the Palermo Cathedral to admire its layered architecture (Arab-Norman core with later Gothic and Neoclassical touches).

Evening: Welcome dinner near La Kalsa. Try Ferro di Cavallo for homey Sicilian classics (hearty pasta alla Norma, mixed fritto), or Osteria dei Vespri for seasonal seafood and a Sicilian wine list that spans Etna to western Marsala. Cap the night with “brioche col gelato” at Brioscià or pistachio gelato at Il Signor di Carbognano.

Day 2: Markets, mosaics, and street food

Morning: Start with espresso and a slice of Setteveli cake at Pasticceria Cappello, or a cappuccino and cornetto at Antico Caffè Spinnato. Dive into Capo Market’s stalls—look for panelle, crocchè, and sfincione.

Join the Palermo Original Street Food Walking Tour by Streaty to taste like a local while learning market history and quirky food lore.

Book: Palermo Original Street Food Walking Tour by Streaty

Afternoon: Step into the Norman Palace’s Palatine Chapel—its 12th‑century mosaics gleam like a starfield. Continue to Teatro Massimo (even non-opera fans love the grand tour). If you want a breezy overview with stops for photos, consider the open-air Palermo: Grand Tour in CruiserCar.

Book: Palermo: Grand Tour in CruiserCar

Evening: Aperitivo in Piazza Sant’Anna, then dinner at A'Cuncuma (contemporary Sicilian tasting menus) or Trattoria Corona for grilled swordfish and caponata. Nightcap at Enoteca Picone, a temple to Sicilian wine since 1946.

Morning of Day 3: Travel from Palermo to Taormina

• Fastest: Fly PMO → CTA (45–50 min), then bus or private transfer to Taormina (about 1 hr). Search intra-Europe flights on Omio (flights); for non-Europe routes, see Trip.com (flights). Total travel time ~2.5–3.5 hrs; fares often ~$50–120 one-way.
• Train: Palermo → Taormina-Giardini (usually 1–2 changes via Messina; ~5–6 hrs; ~$25–45). Book on Omio (trains).
• Bus: Direct coach options (~4.5–5 hrs; ~$25–35). Check Omio (buses).
• Car: ~3.5–4 hrs via A19/A18. Beware ZTLs in both historic centers and plan parking outside.

Taormina

Perched high above the Ionian Sea, Taormina has been a resort since the Grand Tour days—think bougainvillea-draped balconies, alfresco cafes, and a 2,300-year-old Greek Theatre framing Mount Etna like a stage set. Down below, coves like Isola Bella shimmer in every shade of blue.

• Top sights: Teatro Antico (Greek Theatre), Corso Umberto, Piazza IX Aprile, Villa Comunale gardens, and Isola Bella Nature Reserve.
• Don’t miss: granita with warm brioche at Bam Bar, arancini and cartocciata at Da Cristina, and sunset from the Belvedere.
• Beach access: ride the cable car to Mazzarò for lidos (Lido La Pigna is a favorite) or kayak around Isola Bella in calm weather.

Where to stay: For views, stay near Corso Umberto; for beach days, base in Mazzarò or nearby Giardini Naxos. Compare options: Taormina hotels on Hotels.com and Taormina vacation rentals on VRBO.

Day 3: Taormina arrival, Greek Theatre, and a hands-on dinner

Afternoon: Settle in, then wander Corso Umberto’s boutiques and stone archways between Porta Catania and Porta Messina. Visit the Greek Theatre when the light softens—views sweep from Etna to Naxos Bay. For a quick bite, try Da Cristina’s arancini or a slice of scacciata.

Evening: Learn to cook like a local at the beloved COOKING CLASS in Taormina at Chef Massimo HOUSE!! Classes often begin with market shopping, then you’ll prepare fresh pasta, caponata, and a seasonal dessert—and dine on your creations with a view.

Book: COOKING CLASS in Taormina at Chef Massimo HOUSE!!

Post-class stroll to Piazza IX Aprile for nighttime views, then a gelato stop at Pasticceria D’Amore. If you prefer a restaurant tonight, book Trattoria da Nino for grilled prawns and lemony salads, or Osteria RossoDiVino for seasonal Sicilian dishes and a thoughtful wine list.

Day 4: Etna countryside—lava flows, wineries, and small villages (full-day tour)

Head into Etna’s fertile foothills for an intimate day of geology, food, and wine on the Etna Countryside Food & Wine Lovers Tour (Small Group or Private). With a native guide/driver, you’ll explore lava fields and old craters, then visit family-run estates to taste crisp Carricante whites and spicy Nerello Mascalese reds alongside local cheeses, salumi, and olive oil. Pick-up is typically available around Taormina/Giardini Naxos; expect about 6 hours, with time in villages along the slopes.

Book: Etna Countryside Food & Wine Lovers Tour (Small Group or Private)

Back in Taormina, freshen up and enjoy aperitivo at the Belmond Grand Hotel Timeo’s terrace (come for the view), then dinner at Ristorante La Capinera just outside town—Michelin-starred plates that spotlight the sea, citrus, and herbs of the coast.

Day 5: Morning in Taormina or Godfather hill towns, then depart (afternoon departure)

Morning (Option 1): Slow start with granita at Bam Bar (almond or mulberry are classics), then ride the cable car down to Mazzarò for a swim at Isola Bella. Rent a beach lounger at Lido La Pigna or kayak in calm conditions to peek into sea caves.

Morning (Option 2): Film buffs can trace cinema and history on the Godfather vs Mafia Tour & Pasta Lunch (Small Group or Private), visiting the hill towns of Savoca and Forza d’Agrò where The Godfather filmed—plus candid insights into real Sicilian anti-mafia efforts. Includes a light pasta lunch; returns by early afternoon when timed well.

Book: Godfather vs Mafia Tour & Pasta Lunch (Small Group or Private)

Departure: From Taormina, reach Catania Airport (CTA) by direct bus (about 1 hr–1 hr 15 min) or train from Taormina-Giardini to Catania Centrale plus airport shuttle (about 1 hr 30–2 hrs). Compare schedules on Omio (trains) and Omio (buses). For flights within Europe, check Omio (flights); for long-haul, see Trip.com (flights).

Prefer a Taormina cooking-and-sea day?

If you’re swapping the Godfather hills for more time by the water, consider the seaside class Seaview Cooking Class & Taormina local flavors with Chef Mimmo—a family-style experience steps from the beach with recipes you’ll actually make at home.

Book: Seaview Cooking Class & Taormina local flavors with Chef Mimmo

Extra time?

• Syracuse & Ortigia: Baroque streets, the Duomo built into a Greek temple, and the Neapolis Archaeological Park. Consider this guided option if you extend your stay: Tour of Ortigia and the Neapolis Archaeological Park.

Daily coffee, breakfast, lunch, and dinner ideas to mix in

• Palermo (morning): Torrefazione Stagnitta for serious espresso; Pasticceria Costa for cassata and cannoli.
• Palermo (lunch): Nino 'u Ballerino for pani ca meusa (beef spleen sandwich, a true local specialty); Friggitoria Chiluzzo for panelle and crocchè.
• Palermo (dinner): Gagini for refined plates in a historic space; Osteria Ballarò for platters of local cheeses, salumi, and seasonal pastas.
• Taormina (breakfast): Bam Bar for granita + brioche; Pasticceria D'Amore for sweet cannoli and savory rustici.
• Taormina (lunch): Tischi Toschi for rustic pastas; Lido La Pigna for barefoot seafood by the water.
• Taormina (evening): Aperitivo at Morgana Lounge Bar (creative cocktails) then dinner at Trattoria da Nino or Giardini di Babilonia (romantic courtyard).

Wrap-up: In five days you’ll taste your way through Palermo’s markets, climb history’s steps at Taormina’s Greek Theatre, and stand on Etna’s volcanic shoulders sipping mineral-etched wines. Sicily rewards curiosity—follow this route, but leave space for a spontaneous pastry, a side street, and a view that stops you mid-sentence.