How soon to book a flight to Italy

Before Covid, some thought 2-6 months before the flight would yield the best deals. If the airlines ramp up their flights, that might become the rule of thumb again. Meanwhile, you might check Skyscanner.com and GoogleFlights.com for flights from Toronto and Montreal, if you’re on the east coast. For arrival airports this year, at various times, Milan (MXP) Naples (NAP) and Venice ( VCE) were less expensive than Rome’s FCO airport for some flights. You might consider flying into Rome and return home from Milan or Venice, or vice-versa depending on your itinerary. You can sign up for alerts at GoogleFlights and Skyscanner that e-mail you periodically when flights drop in price.
Have a great Trip!

Pre-Covid usually booked tickets (AIrCanada) six to three months in advance of trip, depending on seat sales. Coming from West Coast I had to get to Toronto or Montreal to pick up flight to Europe which could involve a couple of additional flights unless I visited family in UK and flew direct to UK. Flights become available about a year in advance so start looking at the AC website now.

Flights are not cheap and with fuel prices the way they are, I’m not sure that will change.

I’ve recently decided to go to Italy the beginning of September and the prices are crazy. I’m on the East Coast in Canada.

With fuel prices probably going up, if you see a price you can live with you might want to book a flight now but be sure you can change it without a fee. But be prepared for the airline making numerous changes to the schedule between now and next April and having to stay on top of it to be sure it is a scheduling change you like. I booked tickets in February for our August trip to Scotland and the airline has changed it a few times which meant time on the phone (on hold for a long time) or once when it was possible to do so online rerouting that flight. Have an email alert placed on your booking so that you are notified of any changes. Booking airfare is not a one and done deal this far in advance.

I like to use Google Flights to monitor prices. It predicts whether the current prices are a good value or not, and lets you easily compare airports and dates. For example, moving trip dates by just a few days (or maybe even one day) in either direction can save several hundred dollars. You can set up your parameters and get email alerts when your flight cost increases or decreases.

I typically buy 6+ months out, because I don't make any other plans until my flights are booked, and I like to have all my hotels and sight tickets finalized at least 3 months prior to the trip. That's just personal preference and maybe doesn't get me the best flight deal, but I'm ok with that trade off.

After a certain point, the longer you wait the more expensive they will be

I like to use Google Flights to watch flights. I'm on the West coast so use Portland, Seattle, San Fransisco, Los Angeles & Las Vegas as starting points. There are only a few flights to Europe out of PDX (my home airport) I had over 20 watches on Flights. Even at that I look at the date grid to move a few days back & forth. After a month or so you can see trends & recognize a good flight cost. I started looking at Paris flights in March and they started going up. Finally about a week ago a SAS flight came down to the level of March & I jumped on it. By looking over a period of time I can recognize a good fare cost.