A beautiful view of Sicily's Castellammare Del Golfo, showing rocks in an ocean and residential buildings.
Scopello, Sicily.
Credit: Samuel Ferrara

Planning a Sicily holiday?

Sicily holidays are on the rise – and for good reason. With vibrant sunshine, beaches and islands, 7 UNESCO World Heritage sites, excellent food and wine, what’s not to love?

Sicily is the destination I get asked MOST about. Perhaps it’s due to my connection to the island – most of my family is Sicilian, and I myself was born in Catania. I visit around once a year, and used to go for whole summers between school years. I am enormously proud of my heritage.

Which is why it really bums me out when I read of people going and not having an amazing time. Lately I’ve been seeing this a lot.

I really believe this is at least in part to the expectations held about Sicily. The truth is that Sicily is not like other places in Italy. It has so much to offer, but it pays to be prepared. So, on Medium Day (August 12th), my mom, my dad and I are jumping online for a 30-minute live talk on how to prepare for a trip to Sicily.

A panoramic view from a boat on calm blue waters, showcasing distant rocky islands and a clear sky. The scenery highlights the natural beauty of the coastline, ideal for a Sicily holiday talk.
Tre Piscine Mongerbino, Sicily
Credit: Stubborn Travel

What You Need to Know Before Visiting Sicily: August 12th, 4-4:30pm (UK)

We’ll be hosting a talk outlining the basics of planning a Sicily holiday: potential itineraries, geography, the good and the bad, tips and advice. The plan is not to only focus on the positives. It’s to paint a full picture so you have a realistic expectation and a strong plan.

If Sicily’s on your list – this one’s for you! You can register by signing up for Medium Day and adding the talk to your calendar – the time zone will update automatically. It’s free to attend, and there are lots of really cool speakers throughout the day as well.

  • If you’ve been to Sicily, I’d love to know: what do you wish you’d known? What did you love and hate?
  • If you haven’t been to Sicily, what would you like to know?

I think the talk will go quickly, so if we have any questions in advance we can try to work them in.

By the way, I’m actually giving five talks on Medium Day! Three are on marketing, and two are on travel: this one on Sicily, and another one on remote working abroad.

In case you’re interested marketing, I’m also giving the following talks:

  • 5 Questions You Should Ask Before Launching Your Website (3-3:30pm UK)
  • Writing Copy That Sticks: Copywriter vs. ChatGPT (7-7:30pm UK)
  • Copywriting 101: Ask Me Anything (8-8:30pm UK)

That’s it for now… have a fab weekend in the meantime, and maybe see you there!

Ornate gold mosaics fill the walls of the Capella Palatina, inside the Palazzo dei Normanni in Sicily.
Capella Palatina, Palazzo dei Normanni, Sicily
Credit: Stubborn Travel
A vibrant sunrise over the sea in Santa Flavia, a Sicily holiday destination.
A Santa Flavia sunrise. Credit: Stubborn Travel

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