Taormina & Castelmola: Private Day Trip with Sicilian Wine

Summary

Messina to hilltop Castelmola then Taormina’s ancient streets

You’ll taste almond wine in quirky Castelmola, stroll Taormina’s lively streets with a local guide, sample fresh cannoli, and catch panoramic views of Isola Bella before returning comfortably to Messina — all while feeling like you’re part of someone’s Sicilian story.

What’s the experience like?

“You have to try this — but don’t ask what it means,” our guide Marco grinned, sliding over a tiny glass of almond wine in Bar Turrisi. I’d just squeezed past a group of laughing locals, the smell of roasted coffee mixing with something sweet and nutty. Castelmola is perched so high above Messina that my ears popped on the drive up. The view out over the sea was all blue haze and terracotta roofs, and honestly, I didn’t expect to feel so far from everything — in a good way. Marco explained (with a wink) the story behind all those cheeky decorations in the bar. It’s not what you think, he said — it’s about ancient Greek symbols for life and luck. I probably blushed more than I should’ve.

We wandered through narrow lanes where cats darted between sun patches, then tried cannoli that left powdered sugar on my shirt (worth it). The day trip from Messina to Taormina & Castelmola felt like slipping into someone else’s family for an afternoon. On the way down to Taormina, the air changed — warmer, almost salty. Entering through Porta Catania was like stepping onto an old movie set: stone arches, little shops selling lemon soap, voices echoing off cobbles. Our local guide pointed out details I would’ve missed — like how Mount Etna always seems to watch over everything here.

I spent too long staring at the Greco-Roman amphitheatre (didn’t even mind paying extra for the ticket), just trying to imagine all those centuries layered under my feet. The public gardens were quieter than I thought they’d be; birdsong and some old guy reading under a palm tree. By late afternoon we drove out to this lookout for Isola Bella — not sure any photo does that tiny island justice. There was a breeze and you could smell jasmine somewhere nearby. We ended up back in Messina with sticky fingers from one last cannoli and just enough time for Marco to point out that wild clock tower before dropping us off.

Step-by-step itinerary

Day 1 — Explore Messina, Castelmola, and Taormina

• Meet in Messina at tour start
• Admire Madonna della Lettera statue
• Visit medieval village of Castelmola
• Enjoy almond wine and Sicilian cannoli
• Descend to Taormina via Porta Catania
• Explore Greco-Roman amphitheatre
• Visit Lady Florence Trevelyan Public Garden
• Stroll along Corso Umberto street
• View and photograph Isola Bella
• Return to Messina city center
• See Duomo bell tower and astronomical clock
• End tour and return to starting point

Top questions

How long is the day trip from Messina to Taormina & Castelmola?

The tour lasts most of the day, including travel time between Messina, Castelmola, and Taormina before returning.

Is pickup included for this Taormina & Castelmola tour?

Yes, private transportation with pickup and drop-off in Messina is included.

Do you visit Bar Turrisi in Castelmola?

Yes, there’s a stop at Bar Turrisi in Castelmola for almond wine tasting.

Are entrance tickets for Taormina’s Greek Theatre included?

No, tickets for the Greco-Roman amphitheatre are not included in the tour price.

Is lunch provided during the tour?

Tastings such as cannoli and almond wine are included; full lunch is not specified.

Can infants or small children join this tour?

Yes, infants can ride in prams or strollers; specialized infant seats are available.

Are there vegetarian or non-alcoholic options?

Bottled water and fruit juice are provided; specific dietary requests aren’t detailed but can be asked about when booking.

Does this tour include WiFi on board?

Yes, WiFi is available on board during transportation.

What’s included

Your day includes private transportation with pickup and return in Messina, air-conditioned vehicle comfort (with WiFi), bottled water and fruit juice along the way, plus stops for almond wine tasting at Bar Turrisi and fresh Sicilian cannoli before heading back home again.