Arrive, Wander & Your First Sicilian Sunset
Get settled, stroll the corso, discover the ancient theatre with Etna looming behind it, and end the day with aperitivo as the sun drops into the sea. Welcome to Sicily.
🌅 Afternoon — Arrival & Check-In
Catania Airport → Taormina
Land at Catania, grab your bags, and take a pre-booked transfer or rental car north along the coast. The drive itself is gorgeous — the Ionian Sea on your right, Etna's silhouette on your left. Check into your hotel and take a breath. You're in Sicily.
Stay in or near the centro storico if you can. Hotels with terraces and Etna/sea views are worth the splurge — you'll spend every morning and evening on that terrace. Look at Hotel Villa Belvedere, Hotel Villa Schuler, or NH Collection Taormina for that classic Taormina balcony moment.
🏛️ Late Afternoon — Ancient Theatre
Teatro Antico di Taormina
Don't save this — go on your first day when the late afternoon light is golden. This 3rd-century BC Greek theatre is dramatically carved into the hillside with sweeping views of the coastline and Mount Etna. It's one of the most photographed spots in Sicily for good reason. In May, you'll have it without the summer crush.
Walk slowly around the upper tiers. Find a seat in the cavea and just look. The ancient Greeks chose this spot because the view itself was the backdrop to every performance. Twenty-three centuries later, it still works.
📍 Via Teatro Greco, Taormina · €10 · 9:00–19:00 (summer hours) · Allow 45–60 min
"Go to the Teatro Antico late afternoon — the light on Etna is incredible and most tour groups have left by then. We had entire sections to ourselves in May."
— r/ItalyTravel
🚶 Early Evening — Corso Umberto Passeggiata
Corso Umberto I — The Evening Stroll
Taormina's main pedestrian street runs the length of the old town, from Porta Messina to Porta Catania. Join the passeggiata — the Italian evening ritual of strolling, people-watching, and being seen. Duck into side alleys, peek into churches, browse ceramic shops. Stop at Piazza IX Aprile — the terrace piazza with a checkerboard floor and jaw-dropping views of the coast and Etna. This is where you'll want to be at golden hour.
🍹 Sunset — Aperitivo
Aperitivo
Bar Turrisi or Wunderbar Caffè
Wunderbar Caffè on Piazza IX Aprile is the classic choice — Liz Taylor and Richard Burton used to drink here, and the terrace view at sunset is legendary. Order an Aperol Spritz or a Sicilian Nero d'Avola and watch the sky turn pink over the bay. Bar Turrisi in Castelmola (save for Day 3) is the quirkier option — famous for its... let's say phallic decor. Both are institutions.
📍 Piazza IX Aprile · €8–12/drink · From 17:00
🌙 Dinner — First Night
Dinner
Trattoria da Nino
A beloved local trattoria just off Corso Umberto. No pretension, just excellent Sicilian cooking. Start with arancini and caponata, then pasta alla Norma — Taormina's signature dish of rigatoni with fried eggplant, tomato sauce, and shaved ricotta salata. Pair it with a local Etna Rosso. Finish with cannoli — the shells should shatter when you bite in.
📍 Via Luigi Pirandello 37 · €25–40/person · Reservations recommended · Opens 19:00
Alternative: Osteria Rosso Divino for a more wine-focused dinner with excellent antipasti and a deep Sicilian wine list. Cozy, romantic, locals-approved.
Volcano, Vineyards & Wine on the Slopes of Etna
Today you leave the coast and head up Europe's most active volcano. Hike the craters or take the cable car, then descend to the vineyards on Etna's slopes for one of Italy's most exciting wine scenes. This is the day you'll talk about for years.
🌅 Morning — Granita Breakfast
Breakfast
Bam Bar
The most important breakfast of the trip. Bam Bar is Taormina's legendary granita spot — order granita di mandorla (almond) or pistacchio served with a warm, pillowy brioche. Dip the brioche into the granita. This is how Sicilians start their morning, and once you try it, coffee and toast will never be the same. Go early — there's often a line by 10am.
📍 Via di Giovanni 45, Taormina · €5–7 · Opens 7:30
"Bam Bar granita was the single best thing I ate in all of Sicily. The almond granita with brioche — I dream about it. Get there early."
— r/ItalyTravel
🌋 Morning — Mount Etna
Mount Etna — Cable Car & Crater Walk
Drive or arrange a transfer to Rifugio Sapienza on Etna's south side (~1 hour from Taormina). From there, take the Funivia dell'Etna cable car up to 2,500m, then an optional 4x4 shuttle to ~2,900m with a volcanologist guide. Even from the cable car station, the views are otherworldly — lunar landscapes, smoking craters, and on a clear May day, you can see across to Calabria.
If you prefer a lighter experience, skip the summit push and hike the Silvestri Craters at the base station — an easy 30-minute walk around extinct craters with fantastic views. Still volcanic, still dramatic, zero fitness required.
📍 Rifugio Sapienza, Nicolosi · Cable car €30 round trip · Cable car + 4x4 + guide ~€65 · Dress warm — it's 10–15°C cooler up top
Bring a jacket even in May — at 2,500m+ it can be 10°C with wind. Wear closed-toe shoes. The volcanic gravel is sharp. Sunglasses are essential — the reflected light off the lava rock is intense.
🍷 Afternoon — Etna Wine Tasting
Wine Tasting on Etna's Slopes
Descend from the craters to the vineyards. Etna's wine scene has exploded in the last decade — volcanic soil + altitude + ancient Nerello Mascalese grapes = some of Italy's most distinctive wines. Book a tasting at one of these exceptional wineries:
Wine Tasting
Tenuta delle Terre Nere
One of Etna's finest producers. The tasting room overlooks the vineyards with Etna towering above. Their single-vineyard Nerello Mascalese wines are stunning — mineral, elegant, and unlike anything you've tasted. The estate is beautiful and the staff passionate about the terroir. Book ahead.
📍 Contrada Calderara, Randazzo · Tasting €25–40 · Book via email or website
Alternatives: Planeta (larger, polished, great lunch pairings), Benanti (historic estate, pioneered modern Etna wine), or Gambino Vini (family-run, lunch + tasting combos on a gorgeous terrace).
"Etna wine tasting was the surprise highlight of our Sicily trip. We did Gambino — incredible food paired with their wines, stunning views, and the family who runs it couldn't have been warmer."
— r/wine
🍝 Late Lunch on Etna
Late Lunch
At the Winery or Cave Ox
Many Etna wineries offer lunch — reserve it with your tasting. If not, stop at Cave Ox in Randazzo, a charming restaurant in a medieval town on Etna's north side. Rustic Sicilian dishes, excellent local wine, and the kind of meal where you lose track of time. Try the wild mushroom pasta if it's on the menu.
📍 Randazzo or at winery · €20–35/person
🌙 Evening — Back in Taormina
Dinner
Ristorante Vicolo Stretto
A romantic dinner spot on one of Taormina's narrowest lanes. Fresh seafood is the move — try the spaghetti ai ricci di mare (sea urchin pasta) if it's available, or the catch of the day grilled simply with lemon and olive oil. The intimate setting and candlelight make this a perfect couple's dinner. Pair with a chilled Etna Bianco.
📍 Via Vicolo Stretto, Taormina · €35–50/person · Reservations essential · Opens 19:30
Beach Morning, Hilltop Village & a Grand Farewell
Your last full day. Morning on Sicily's most beautiful beach, afternoon in a hilltop village with almond wine and infinite views, and a farewell dinner you won't forget. Soak up every last drop.
🌅 Morning — Villa Comunale Gardens
Villa Comunale (Public Gardens)
Start the morning with a peaceful stroll through Taormina's public gardens. Built by an eccentric Englishwoman, Lady Florence Trevelyan, in the late 1800s, the gardens are full of exotic plants, whimsical Victorian follies (she called them "beehives"), and stunning views down to the coast. It's quiet in the morning — just birdsong and the scent of jasmine. Grab a bench and breathe.
📍 Via Bagnoli Croce, Taormina · Free · 9:00–sunset
🏖️ Late Morning — Isola Bella
Isola Bella — The Pearl of the Ionian
Take the Funivia cable car down to Mazzarò beach, then walk along the shore to Isola Bella — a tiny island connected to the mainland by a narrow sand strip. The water is crystal-clear turquoise, framed by dramatic cliffs. In May, you'll have space to breathe — by July this beach is shoulder-to-shoulder.
Rent a pair of sunbeds (€10–15/each) or lay your towel on the free pebble beach. Swim out to the island — the snorkeling around its rocky edges is surprisingly good. The water will be fresh (~19°C in mid-May) but absolutely swimmable.
📍 Below Taormina, via Funivia (€3 each way) or steep staircase · Nature reserve entry €4 · Bring water shoes — it's pebbles, not sand
"Isola Bella in May was paradise. Crystal clear water, barely any crowds. We spent the whole morning swimming and sunbathing. Take the cable car down and walk — it's stunning."
— r/ItalyTravel
🍝 Lunch — Beachside
Lunch
Lido La Pigna or Ristorante Da Giovanni
Eat with your toes still sandy. Lido La Pigna at Mazzarò has a lovely terrace right over the water — fresh grilled fish, insalata di mare, and cold white wine. Or Da Giovanni near Isola Bella for simple, excellent seafood pasta. Order the fritto misto (lightly fried mixed seafood) and a cold Birra Messina. You're on a beach in Sicily — act accordingly.
📍 Mazzarò Beach / Isola Bella · €20–30/person · 12:00–15:00
🏔️ Afternoon — Castelmola
Castelmola — The Village Above the Clouds
Take a taxi or drive 10 minutes uphill (or hike the steep ancient path in ~30 min) to Castelmola, the tiny medieval village perched above Taormina. If Taormina has the best views in Sicily, Castelmola has the best views of Taormina. From the ruins of the Norman castle at the top, you see Etna, the coastline, Taormina below, and the sea stretching to forever.
Wander the stone lanes, peek into the small churches, and end up at the main piazza for the main event.
Afternoon Drink
Bar Turrisi
The most infamous bar in Sicily. Four floors of... phallic art. Everywhere. The almond wine (vino alla mandorla) is the house specialty — sweet, nutty, cold, and perfect on a warm afternoon. Order it on the terrace with views of Etna and try to keep a straight face at the decor. It's hilarious, charming, and genuinely one of Sicily's great experiences.
📍 Piazza del Duomo, Castelmola · €5–8/drink · Open daily
"Bar Turrisi in Castelmola is an absolute must. The almond wine is delicious, the views are insane, and the decor is... well, you'll see. My partner and I couldn't stop laughing."
— r/ItalyTravel
🌙 Evening — Farewell Dinner
Farewell Dinner
La Capinera
Your splurge meal. La Capinera is a Michelin-starred restaurant on the beach at Spisone, just north of Taormina. Chef Pietro D'Agostino serves inventive Sicilian seafood — think red prawn crudo, pasta with sea urchin butter, and deconstructed cassata. The terrace overlooks the water, and at sunset the whole scene glows. This is the dinner you'll remember from this trip.
📍 Via Nazionale 177, Spisone · €80–120/person with wine · Reservations essential — book weeks ahead · Closed Tuesdays
Alternative: Andreas Restaurant on Corso Umberto for excellent seafood in a less formal (but still romantic) setting. Their grilled swordfish and pasta con le sarde are outstanding. €40–60/person.
One Last Granita, Then Arrivederci
A gentle final morning. No agenda, no rushing. One more granita, one more stroll, and carry Sicily home with you.
🌅 Morning — Last Breakfast
Breakfast
Granita Encore — Bam Bar or Your Hotel Terrace
One more granita con brioche. This time try a different flavor — pistacchio if you had almond, or gelsi (mulberry) if they have it. Eat it slowly on the terrace. Look at Etna one more time. This breakfast is the taste of Sicily you'll crave on the flight home.
📍 Bam Bar or café of choice · €5–7
🚶 Late Morning — Final Stroll
Corso Umberto — Morning Light
Walk the corso one more time in the quiet morning light, before the day-trippers arrive. Pop into a ceramics shop for hand-painted Sicilian pottery — the testa di moro (Moorish head planters) are the iconic souvenir. Pick up a bottle of Etna Rosso and some local pistachios from Bronte to bring home.
For authentic ceramics, look for shops that say "fatto a mano" (handmade). The mass-produced stuff is obvious — real Sicilian ceramics have small imperfections and richer colors. A hand-painted plate runs €15–40 and makes a beautiful, lasting souvenir.
✈️ Afternoon — Departure
Taormina → Catania Airport
Allow 60–90 minutes for the drive to Catania airport, plus time for any traffic. If your flight is late, consider a quick stop in Catania itself — the fish market (La Pescheria) is wild and wonderful, and you can grab one last arancino from a street vendor near Piazza del Duomo.
If you bought wine at Etna wineries, pack it in checked luggage with clothes wrapped around it. Most shops will bubble-wrap bottles if you ask. Alternatively, many wineries can ship to the US/EU.
💰 Budget Breakdown
Estimated costs for two people, 3 nights. Taormina is mid-range by Italian standards — not cheap, but incredible value for what you get.
| Category |
Estimated Cost (for 2) |
Notes |
| Accommodation (3 nights) |
€400–900 |
Boutique hotel with view (€130–300/night) |
| Food & Drink (4 days) |
€350–550 |
Mix of trattorias, beach lunch, one splurge dinner |
| Mount Etna (cable car + wine) |
€120–200 |
Cable car €60/2 + wine tasting €50–80 + transport |
| Transport (airport + local) |
€120–180 |
Airport transfers, Funivia, Castelmola taxi |
| Attractions |
€30–50 |
Teatro Antico, Isola Bella nature reserve, gardens |
| Beach & Misc |
€40–60 |
Sunbed rental, souvenirs, gelato, tips |
| Total for 2 |
€1,060–1,940 |
~€530–970 per person |
This does NOT include flights. Budget can flex significantly based on accommodation — a simple B&B with a view can be €100/night, while a luxury hotel with pool runs €300+. The food and experiences are the same magic either way.