Snowbirds in Italy: How Tony, 65, Makes the Most of the Shoulder Season Every Year

While most Canadian Snowbirds head south to chase the sun, Tony P., a loyal soNomad client from Toronto, chooses a different path: Italy. For the past 20 years, he’s been swapping snow for slow travel, planning his getaways during the shoulder season when the weather is mild, prices are lower, and the pace is just right for exploring.

He divides his time between Rome, Florence, the Amalfi Coast, and the small town where his parents once lived. These month-long stays allow him to reconnect with his roots while enjoying the charm of northern and central Italy.

Wondering what spending a month in Italy really looks like? Find out why travelling during the shoulder season might be Italy’s best-kept secret, and how it could become part of your own winter escape.

As a Snowbird, Why Did You Choose Italy for a Long Stay?

“One of the main reasons I picked Italy was convenience. There is usually a direct flight from Toronto to Rome, which makes the trip straightforward. 

Once you're in Rome, it becomes an easy starting point to explore both the north and the south. It felt like the ideal place to begin a longer stay and move around at a relaxed pace.”

How Did You First Discover Italy as a Snowbird Destination?

“My parents are Italian, but I was born here in Canada. They came over about 100 years ago seeking a better life. I’ve always felt a connection to Italy, and if I ever had the chance to spend six months there, I would definitely take it.

Since I don’t have any family left in Italy anymore, my time there was all about touring and exploring the country.”

Before Travelling to Italy, How Did You Do Your Research and Prepare?

“Honestly, I usually just book my hotels and Airbnbs from here and go. I don’t really do much research myself. But the family members who join me take care of the planning and look into places they want to explore.” 

Where Did You Stay in Italy?

“We stayed in a whole house in Formia, which is just north of Naples. It had two bedrooms and two bathrooms, and it was right by the beach. It costs around 200 Canadian dollars a night.

Italy is still busy, especially Rome, which is bustling all the time. In the smaller towns, it’s easier to find a good Airbnb, and things feel a bit more relaxed. Most places stay open, so there’s always something going on.”

What’s the Weather Like in Italy During the Winter? Is It Warm Enough for Swimming?

“We usually go in October or early spring, like April or May. The shoulder seasons are fantastic with temperatures around 18 to 24 degrees Celsius. 

Although the water isn’t quite warm enough for swimming, we enjoy spending time at the beach, just relaxing and taking in the view.”

Did You Feel Safe During Your Stay in Italy?

“Overall, yes. Every time we visit, we meet really pleasant people. We did see a pickpocket once, but that can happen anywhere. It never happened to us, but it’s a good idea to stay alert with your belongings.

People there don’t seem to chase owning a lot of land or things. They’re happy with their apartments and the simple lifestyle.

If you’re not comfortable driving in Italy, it’s better to use public transit or taxis. Just make sure to prearrange your taxi fare or insist on the meter because there are some drivers who might try to overcharge. They’re there to make a dollar, so a little caution helps.

In case you decide to drive, the highways are well marked: the left lane is for passing (and fast drivers in Ferraris), the middle lane is for regular speeds around 100 km/h to 120 km/h, and the right lane is for slower vehicles like mopeds.”

How’s the Food in Italy? Any Local Dishes or Flavours That Stood Out to You?

“Surprisingly, I never put on weight when I’m there. The food feels almost heavenly: no preservatives, everything fresh every day, from the bread to the desserts. It’s impressive how they keep that level of quality.

For me, Italy has the best food in the world. I’ve had great meals in Portugal and Spain, but nothing beats Italy. Take pasta for example, in North America, we have 25 different pasta dishes, but in Italy, they focus on just a few classics, like aglio e olio or cacio e pepe, and they do them perfectly.

One thing that stands out for me is the Florentine steak. It’s so special that it’s actually illegal to send it outside Florence. The steak is huge, almost the size of your plate. Normally, I don’t eat that much, but with this steak, you want to finish the whole thing. The cattle there are raised differently, no chemicals, and you can really taste the difference.”

If You Don’t Speak Italian, Is It Possible to Travel There?

“Well, I speak the language, so it’s pretty easy for me. But even if you don’t, most of the younger generation, probably 80 to 90%, speak English. 

Sure, the 90-year-old nonna probably won’t, but her kids definitely will. So you’ll be just fine getting by.”

What Are Some Things That Shook Up Your Routine or Suprised You During the Trip?

“One thing that really surprised me was in Vatican City: there’s a McDonald’s that feels nothing like back home. They serve beautiful desserts, great coffee, and espresso. You can grab a sandwich there without having to eat a burger. 

Also, dinnertime usually starts around 9 p.m., and most places close between midnight and 2 a.m., so the nightlife rhythm is quite different.

This year wasn’t the best to visit Italy because of the Jubilee, which only happens every 25 years, and the new Pope’s arrival brought tons of tourists. The locals weren’t too happy with all the crowds and celebrations, so I’d say it’s better to pick another year.

I’ve noticed locals get better prices at restaurants. I’ve tried to blend in, but they could tell I wasn’t from around there.

And a funny one: the Autogrill, a gas station on the highway, where you can order a steak or a full plate of pasta. It’s not what you’d expect from a rest stop!”

Is the Cost of Living in Italy More Expensive or Less Than in Canada?

“Overall, I’d say it’s a bit lower than back home.”

Transportation:

“Most people walk or use trains. The service at the train stations can be intense, but prices are reasonable. 

Gas is more expensive than here, but many cars run on diesel, so they get better mileage. Plus, they have way better cars than we do.”

Groceries and Restaurants:

“Groceries are about the same price, maybe a little cheaper depending on where you shop. There’s no Costco in Italy because people shop daily. They get fresh fruits, vegetables, and meat every day — no need to stock up for the week like we do.

Eating out is quite affordable. Outside the tourist spots, you can enjoy a fantastic meal with wine for around 20 euros per person. The quality is phenomenal!”

Accommodation:

“Costs are similar to other European spots. A hotel room might go for 300 Canadian dollars, but you can find places for around $150, especially if you stay outside tourist centres.”

Did You Discover Any Tricks to Save Money During Your Stay in Italy?

“One thing we did was have lunch on our own sometimes. We would grab focaccia and mortadella from the grocery store for about 5 euros, and it was very large, almost the size of your head. We were filled up and it didn't cost much.

Also, many hotels include breakfast. They often served an American-style breakfast, but Italians usually skipped it because it was too heavy for them. So we enjoyed it when it was offered, and that saved us some money.”

What Day Trips or Excursions Do You Recommend?

“I usually book trips for convenience. On the Amalfi Coast, you can take a ferry to Capri, which is definitely worth visiting.

In Vatican City, I recommend booking skip-the-line tours for the churches. They are not cheap, but the convenience of avoiding long waits makes it worthwhile.”

How Did You Stay in Touch With Family and Friends During Your Extended Stay in Italy?

“I put my phone on airplane mode and used Wi-Fi, which is available almost everywhere in Italy. For driving, I got my son-in-law to set up Google Maps offline for me to use.”

Did You Have Travel Insurance for This Long Trip to Italy? Did You Ever Need to Use It?

“Yes, I always have my travel insurance through soNomad. On one of our cruises, there was a death in the family during a transatlantic crossing, and we had to cut the trip short. soNomad covered all the expenses, and the reimbursement process was smooth. I got everything back in less than a month. That’s why I stick with soNomad. 

I’m very happy with my agent Shannon, who helped me a lot, and I’ve recommended her to many people. Someday, I want to take her to Italy with me!”

Finally, What Would You Say to Someone Who’s Thinking About Becoming a Snowbird but Still Hesitating?

“I’d say, just go for it! Language isn’t really a barrier. If you book an Airbnb, you can stay longer and really soak up the lifestyle. 

Everything in Italy is about enjoying life: music, dancing, and a general happiness that’s contagious.”

Experience Winter the Italian Way!

Year after year, Italy keeps delivering for Tony: warm days, unforgettable meals, and the kind of simplicity you can’t quite find back home.

If you’re a Canadian snowbird who thinks the idea of quiet piazzas, off-season prices, and morning markets sounds like a better way to spend winter, maybe it’s your turn to try Italy’s best-kept travel secret.

And before you go, don’t forget to get travel insurance. Get a quick quote with soNomad and you’ll be ready to indulge in La Dolce Vita.