Learning Italian in Sicily: What Happens When You Go Slow and Stay Long

I’m standing in Catania airport, that familiar anxiety rising as I intently watch the baggage claim belt, waiting for my bag to arrive. And I wait. And wait some more. It’s Italy, they’re more relaxed, maybe it just takes more time. And then I realize I’ve waited past the point of waiting – while simultaneously messaging my driver in WhatsApp about the delay, so he doesn’t leave me stranded without clothes or a ride. Isn’t this a fine start to learning Italian in Sicily?

Wait, back up. Did I just say 3 weeks in Sicily? Yep, I sure did. Back in 2018, I took extended time off to travel, reassess what I really wanted in my career and in life, and I had this urge to spend a summer in Italy. I didn’t want nonstop tourist mode. I was looking for slow, real-life immersion, so I could understand if it’s somewhere I would want to end up permanently one day. Is it as magical to live there as it is to visit? I just had to find out. I also wanted to explore off the beaten path places, and Sicily had been on my radar for some time. 

For my full guide to solo travel for women over 35, strt here →

The Plan – Learning Italian in Sicily

So I enrolled in a language school in Sicily for 3 weeks, figuring that would be my first introduction to living the Italian life, and I’d decide on the next stop once I was well into this one. That’s how I ended up at Catania airport, waiting for the bag that never came. So I did what I could. I filed my report, caught my ride to Taormina, and figured the bag would sort itself out. (Spoiler alert: it did.) 

Read on to get my take on what 3 weeks in Sicily was like. If you’ve found this looking for a day-by-day itinerary, I’ve got that covered in my 2 weeks in Italy article. What you’ll find here is the slower, messier, more personal version of Sicily, including practical notes about language school, neighborhoods, and why Sicily rewards you most when you stop rushing.

Before Syracuse: A Few Days in Taormina (and a Birthday Sunrise)

I arrived in Taormina the day before my 42nd birthday. I was still in shock that I was actually doing this. The missing bag put a slight damper on my arrival, but they knew the bag was inadvertently left back in the US, and promised to deliver it to my hotel when it arrived. That, coupled with the fact that I also had a carry-on with clothes and essentials, gave me peace of mind that I would be covered in the interim. 

A couple of friends had told me all about the town, encouraging me to visit, and its charm was on full display as I arrived. I strolled around, amazed at how we were perched on the hillside. My hotel was a sanctuary, with artwork throughout and stunning views at every turn – my room included. The memory of waking up on my birthday to the sun rising over the Ionian Sea is still vivid in my mind. I was 42. I had a missing bag, a life I was rebuilding, and a balcony with a view. In that moment, that felt like enough. 

I arrived slightly before high season, so it was as if I had parts of the town to myself. The pace was slow, the views caught my breath at every turn, and the weather, well, she was as unpredictable as my luggage arrival was. But that didn’t stop me from getting out and exploring (I lived in Seattle at the time, so a little rain was not going to hold me back). I saw sun to rain to hail to clouds and back to sun all in one day, and Taormina was just as lovely in each of her weather moods.

What to See, Eat, and Do in Taormina

My hotel was right in the center of town, so walking everywhere was a breeze. The Greek theater was a sight to behold, with views straight out to the sea. Not far from there were lovely gardens that felt like stepping back in time. I could picture the citizens from eras gone by strolling these same gardens, walking these same streets, and had a deep think about how much history this place must have seen through the years.

After a wonderful breakfast at my hotel each day, I sampled different restaurants around town for lunches, aperitivos, and dinners. I like to stay active, so I hiked to the top of the hill above the town, where I could see for miles. There were some ruins from a fort or castle of some sort, with beautiful flowers growing in it. A perfect representation of the old and new, nature reclaiming what humans once built over. I then hiked down down down to the beaches below, visiting Isola Bella and relaxing on the shore. It was the perfect place to exhale before my deep dive into Syracuse and student life.

Visiting Mount Etna was the main dish fulfilling my hiking craving. It was a day trip from Taormina, and I went with a guided group. The terrain is so different, but the experience was fantastic. Hiking on an active volcano, visiting the small villages nearby, and dining in a remote lodge before heading back gave me the chance to see a whole other side to the area before moving on to my ‘real Italian life’ and my remaining 3 weeks in Italy. And luckily, my luggage arrived in Taormina before that next chapter began.

If you want the full breakdown of what to do in Taormina, I’ve got you covered over in my 2 weeks in Italy itinerary. 

Why I Spent 3 Weeks Learning Italian in Sicily (And Why You Might Want To) 

During my prior Italy travels through Northern Italy and the Cinque Terre, I befriended our local guides. We stayed in touch, and they were some of the first people I reached out to when considering coming back for an extended stay. One of them, now running her own guide company, encouraged me to look at Sicily, and Siracusa in particular. 

She raved about the fact that Siracusa was one of Sicily’s more beautiful cities that had a great blend of history, art, and culture, and was not huge but was still big enough to have some vibrant energy. Combine that with the great reputation of the language school there, and she convinced me that I had to give it a look.

And that I did. I also looked at schools in Puglia and Calabria, as I had in my head that I’d start at the bottom of the ‘boot’ and work my way to the top. At the time, Sicily was a bit more used to seeing solo women travelers (think that’s expanded to these other regions now), and with the firsthand recommendation of my friend, my decision was made. 

But why a language school at all? Well for me, I wanted to have true immersion in the culture. That is much easier to do when you can actually speak the language. It also provided a built-in community with structured days and a sense of purpose. It’s wonderful for solo travelers, as you organically meet people at school, which naturally leads to socializing outside of class – dinners, day trips, and seeing the sights around town were often done with my newfound friends.

Learning Italian in Sicily? Really??

OK, but why Sicily? Everyone else in Italy told me Sicilian dialect was awful, and not where you’d want to learn. But that just shows they didn’t know about this little gem I had found. The Italian Academy is a small, intimate school, right next to the Parco Archeologico della Neapolis. It has legit Greek ruins as a neighbor that we saw day in and day out, vs a tourist attraction you visit once. The grounds were lovely, with bougainvillea, large gardens and trees throughout. You felt at peace there, a little respite in the middle of the city. And yes, they taught Italian without leaning into the Sicilian dialect. My pronunciation, while not perfect, was respectable as I traveled through Italy after my 3 weeks in Sicily.

And the people? They were grand, too. The staff and teachers were so kind, as were the other students. The school attracted a wide array of folks. College students studying abroad, people in their 20s in their gap years, couples in their 60s who had all the time in the world for this kind of trip; people studying for business; and people like me, mid-life and wanting to hit the reset button. We all connected, blended, and bonded, creating this beautiful community. They forgave my basic Italian (thanks, Duolingo), and laughed with me every time I accidentally answered in Spanish. We studied, dined, and explored together, and it was lovely. I even reconnected with two of them in Naples when we both were there at the same time. There’s something about a unique shared experience that really brings people together.

What to Know Before You Go 

Classes are typically in the morning and the siesta breaks are real. They will catch you off guard if you’re American expecting a market stop after school. 

Where you stay can make a difference. If you’re right by the school, you’re farther from Ortigia Island, a UNESCO heritage site that is also an adorable walkable island with shops and restaurants. If you stay in Ortigia, you’re farther from the school. Ideal spot is about midway in between the two, making it about a 15-20 minute walk to either.

It may seem daunting to undertake 3 weeks in Sicily solo, but rest assured that if you enroll in a language school, it becomes your solo travel gateway. You may arrive alone, but you don’t stay that way for long. This has been my experience not only in Sicily, but every international school I’ve attended.

What Living in Sicily for 3 Weeks Actually Looks Like 

Do you ever wonder what it would feel like to not just visit a place but actually live there for a while? To shop at the same market twice? To know which café makes your coffee the way you like it? Well that’s exactly what 3 weeks in Sicily gave me. 

I had my local baker who knew what bread I wanted each morning. My local market that stopped being a quaint peek into Italian culture, and instead was my local go-to. I mastered the silver moka pot for coffee every morning, and whipped up fresh lunches during siesta every afternoon. And yes, I dealt with real issues like WiFi being down, water leaks, and trying to converse with repair people in my remedial Italian. And all of it – the fun, the frustrating, the in-between moments – are what made it feel like real life, and why I loved it so.

The Apartment Life 

The school found me an apartment which was about midway between the school and Ortigia Island, which made getting around quite easy – I walked everywhere. If they are booking for you, request a similar location.

I typically made coffee before school, never tiring in seeing the little silver moka pot percolate. It was a small ritual that reinforced Italian life. I’d head home late afternoon after doing some homework in the school gardens, and make a fresh lunch with ingredients from the market.  

Evenings varied from staying in to heading to over to Ortigia for a meal and drinks out on the town. Weekends were made for day trips – from Noto for Infiorata, the flower festival, to Catania for the fish market, and so many more. We realized what a great base Syracuse actually was. Another reason this was a great choice for 3 weeks in Sicily.

Learning the Siesta (the Hard Way) 

My first Sunday in Syracuse, I learned exactly how Sicilian time works, and I learned it the hard way. I arrived ready to get settled – groceries, SIM card (this was before the eSim days), a walk around the neighborhood. And yet, every single thing was closed. Not just a little closed. Completely, unambiguously, deeply closed.

So I walked, figuring I’d get a sense for the (closed) neighborhood. Yet I forgot to bring my address, or even take a picture of my building. Which made finding home that much more of an adventure.

It really highlighted the difference between American productivity mode to Sicilian time. Sicily prioritizes the things that really matter in life, while we Americans tend to treat those things as optional, or worse, inefficient. Time with family, time to eat fresh food, time to rest. It’s truly a different pace and a different way of living. Every time I live it I tell myself I’ll come home and keep it up, but the American culture makes that quite difficult. Even more of a reason to cherish it when you get to experience it. Rather than get frustrated (ehm, yes I may have been a tad frustrated on day one), embrace the benefits of it and settle in. 

The Rhythm of a Week 

Weekdays entailed school in the mornings, homework, wandering or siesta in the afternoons, and dinner and wine in the evenings – some of the best being by the water, overlooking the sunset on Ortigia Island. Saturdays and occasional days off were for excursions. This is such a different approach to a week for a student vs a tourist in the same city, but I wouldn’t have had it any other way.  

Ortigia Island and the Syracuse You Actually Get to Know 

Ortigia Island is the ancient island heart of Syracuse and a UNESCO site. It’s quaint, gorgeous and walkable. When you live there, you see the bustle of the tourists during the day, then the calm of the city in the evenings. You see the locals come out to play, remembering that life keeps living in a popular tourist town (you’d think I’d have this top of mind as I live in a tourist town, but alas, we sometimes forget these things.)

We lived in walkable distance to the Ear of Dionysius and the ancient Greek Theater. My roommate and I got tickets to an actual play performed there, compared to tourists who may just see the ruins as a piece of time gone by vs a living venue. We popped next door to The Parco Archeologico della Neapolis on a school break, realizing this was on people’s must-see list as a tourist. 

Having time to relax and not feel like we had to rush through everything in a few days set a completely different tone. Watching the Sicilian light in the evenings on the water, seeing it change each time as the weather and sunset were slightly different. Soaking in the baroque architecture, noticing a new detail every time we walked by. 

Understanding the difference between the island and the mainland part of the city. Both were working, but they worked in tandem, in harmony, feeding each other in a way. Syracuse felt more like a ‘normal’ city for locals, vs the curated, polished tourist cities you often visit. Don’t get me wrong, I love those. But seeing this other side gave a real sense for what real life would be like there. And part of what made it feel real was the people I started to actually know.

Is Syracuse Worth It Without the Language School? 

Short answer: absolutely yes. If all you have is that normal vacation time and want to visit Sicily, I highly recommend adding Syracuse and Ortigia to your itinerary. I’ve even crafted an itinerary for 2 weeks in Italy with them included. With Greek history, the art, the baroque architecture, and Ortigia Island, a UNESCO heritage site, there is a ton to see that will make your time worthwhile. It also becomes a great base for trips to smaller towns in the area, so you aren’t packing up and moving each night. Add it to your trip, you won’t be disappointed.

The People You Meet When You Stay Long Enough 

My first friend I met was my roommate. She was much younger than I was, only 18 or 19 years old, from Germany. We got to know each other and how we lived, what we cooked, and what we liked to do for fun. We shared our cultures, commemorated in our learning process, and went on several jaunts around town and Sicily together. She was a gem, and I’m lucky we were paired together.

I also befriended other students in school. The couples from Australia, the gentlemen from England and Germany, and even the instructors. Through homework practice, class lessons, dinners around town, and nights out, we had a ball. That reconnection later in Naples? That kind of thing doesn’t happen when you’re just passing through.

That’s the contrast with tourist travel. When you’re just passing through, you meet people briefly. When you stay, you form actual bonds. That was an unexpected benefit of my 3 weeks in Sicily.

Is Learning Italian in Sicily Right for You?

Are you inspired and now wondering “could I actually do this?” 

The good news is, it’s more accessible than you think. It doesn’t have to be three weeks – shorter sessions exist, and many folks took part in these. Bonus is you do not need to speak any Italian going in (take it from me!). The Intro level class is real intro level, and there’s no shame in that game.

You might think this kind of trip costs a fortune. It really doesn’t. Enrolling in language school and renting an apartment is often comparable to (or less than) hotels for the same period. I was amazed at the affordability. My three weeks, including the apartment was honestly comparable to what I’d spend on hotels.

If you’re a solo traveler who wants built-in community, an Italy lover who wants to go deeper, or anyone who’s fantasized about living somewhere instead of visiting, this is for you. You’ll have a schedule, a community, and a home base, which makes the whole thing less intimidating than it sounds. 

How to Plan a Language School Stay in Sicily 

Planning to do a language school stay in Sicily? These tips are for you:

• Book housing through the school when possible (they coordinate apartments and roommate situations) 
• Arrive a few days early to land in another part of Sicily before your program starts (Taormina is perfect for this) 
• Bring good walking shoes. You’ll cover more ground than you expect 
• Download an eSIM before you land. Airalo is my lifeline overseas. You even get a discount with my code ANDREA68732 
• Budget for wine, dinners out and day trips – affordable and well worth it

What to Pack

Apartment life doesn’t require a different approach to packing than a regular trip. My 431 packing system works just as well here. 

What I Learned About Myself by Staying in One Place 

You stop performing ‘tourist’ and start just living. There’s something that happens when you slow down and stay put. When you let a place actually know you a little. It also gives you time to think, to process. Your mind isn’t occupied with planning the next thing or discovering the next tourist site. You can just be, and rediscover who you are and what you truly love.

I know that I’m a person that likes to have a purpose. I like having a bit of structure and routine. 3 weeks in Sicily gave me that, but also gave me room to relax. I had a routine, but it was one of exploration and discovery. I had a purpose, but for no one but myself. It was comfortable yet strange.

And I forced myself not to plan out every detail, so I could get more comfortable with spontaneity, without knowing what’s next. Case in point: I didn’t have a plan for where I was going when these 3 weeks in Sicily were up. I knew Italy, but not specifically where.

That used to be something my planning brain wouldn’t let me do. Here, I made it happen – or not happen, as it were. Eventually I knew what felt right. I booked a last-minute hiking trip in Amalfi, got a plane ticket, and headed off lighter than I would have been if I had been laden with details. I was able to focus on the here and now, vs planning for next. And that little shift? It grounded me in the experience in a way that I didn’t know what possible – something I need to remind myself of even today.

Could Sicily Be My Forever Home?

3 weeks in Sicily gave me a good sense for what it might be like to actually live there. That seed had been planted on prior tourist trips to Italy, but this trip made those seeds sprout. By the time I left, I was conversing more comfortably. Understanding more vocabulary. And realizing that yes, I could stay and make a life of this. It’s funny. The Spanish-Italian brain blending is a good metaphor: sometimes you reach for the familiar and get the wrong thing, but you get there eventually.

Conclusion 

3 weeks in Sicily changed the way I think about travel, and how I think about life. It’s not about what I saw, but what I actually experienced. Taormina gave me a birthday sunrise and a volcano hike. 

Syracuse gave me a routine, a community, and a taste of what it would mean to really be somewhere else. It reminded me that I can learn new things, I can get comfortable with the uncomfortable, and I can push my comfort zone and grow. It reiterated that fact that human connections are everything, and kind people exist everywhere. Those were things I needed reminding of at this time in my life. I enjoyed it so much I ended up doing another language school later that summer in Montepulciano (more to come on that one another time). 

For anyone who’s ever wondered what it would be like to live somewhere instead of just visit, Sicily is a very good place to find out. If you want to plan a trip like this, I am happy to help. 

Wherever you go, however you do it, I want you to have a trip to remember. 

Happy travels, kindreds! 

RELATED POSTS

Ready to head to Sicily? 

• Take a look at my ideal Sicily itinerary, a perfect next step for anyone who wants to explore the region
• I visited the Amalfi Coast after my time in Sicily – check out my full itinerary and hear about my Sicilian friend reunion.
• Here’s more reflection on what I learned during my 3 months in Italy – different lens, same trip 
• Northern Italy is great too. My mom, her cousin and I had a wonderful trip there.  Read about our travels and see our ideal itinerary here: Northern Italy Family Girls Trip
• This was part of my Eat-Pray-Love Trip, but there’s different solo trips out there. Here’s 6 Kinds of Solo Trips to Take
• If you’re nervous about going it alone, take a look at How to Start Traveling Solo
• It’s true there are The Hard Parts of Solo Travel, but they’re well worth it
• Ready to plan? Take a look at How to Plan a Multi-Week International Trip
• My 431 packing system will help make sure you bring only what you need – get your free guide here

HELPFUL LINKS

Ready to book? Here are my go-to resources for flights, packing, planning, and staying connected:

• Work With Me
  • Need help planning your 2026 travel? Contact me here for personalized itinerary assistance!
  • Want more information on the benefits of using a travel advisor? Learn more here
• Planning Resources
  • The Italian Academy Syracuse for language school details and booking 
  • Viator / GetYourGuide for Mount Etna guided hike options 
  • Parco Archeologico della Neapolis, the official site for tickets and hours 
  • Visit Sicily (official tourism board) for general destination planning
• On-the-Ground Tools:
  • Airalo: eSIM for international data – a godsend! Use ANDREA68732 for $3 off
  • TripIt: Forward all of your confirmations and have your entire trip at a glance
  • Google Maps: download city maps, save your hotel, restaurants and key sights for easy navigation
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