When to purchase flights to Italy for September Tour?

When we booked our tickets to Italy this March, Sunday was the best day of the week to purchase tickets. Tickets were $400 cheaper than what we had seen all week (with better itineraries as well) just one month out. September is high season, though, and gas prices seems to be climbing again...

Our friends who are going to southern Italy in August bought last week on a Sunday and seemed happy.

We bought our ticket to Sicily in December for May. My observation is that we had already missed the best prices. I kept waiting for them to come back down. For our routing the best prices were about six weeks earlier. My daughter and her husband bought tickets on Turkish Air in March (two months out) that were priced the same then as they were in December. Delta, however, was much cheaper in early December which was six months out.
We ended up buying tickets to Rome and staying there two nights because routing was $400 cheaper than going directly to Sicily.
In other words, if you find something you can live with, I would buy it. I doubt it will get better but it may not get any worse.

I bought my flights for September last November. Prices have almost doubled since……. Look for a price you can live with and buy.

I bought mine for September two months ago — I used Delta’s fare calendar and found one pair of dates that was much cheaper than all the other outbound/return combos so I jumped on it. Checking the same routing and dates now, I see that the fare has since doubled. So I agree with the advice to buy if you find a price you can live with and don’t expect that prices will go back down. Good luck!

Thanks everyone who replied. We watching the fares every day now so we’ll grab them once we see one that looks good.

You can set up Google Flights price alerts, in addition to researching previous price fluctuations .
Good luck!

I've been watching the flights and the prices only seem to be climbing.

Have no reason to expect a change in direction

The International Civil Aviation Organization has projected that global air passenger demand will return to pre-pandemic levels by the end of March, and exceed 2019 figures by 3% by the end of the year.

We've been looking for similar flights and using Google Flights to track prices. Unfortunately, I'm sure we've missed the window for better prices, and occasionally we catch price drops but for Premium Economy or better for our segments (Chicago > Milan) are going to be $4k and up, regardless of airline.

Been monitoring credit card points/airline mile options to help offset the eventual costs.

My 2cents… book asap

I realize we do not have main cabin tickets, but here are some numbers based on our situation:
Last year we booked two tickets in Delta One, open jaw (May into Milan, June out of London) which cost only $330 (total for two tickets) more than this years two tickets in Premium Select, round trip to Rome (late September/Early October).
This years tickets were purchased in mid February and the the same tickets, in the same class are now $2000 (total for two tickets) more.
If you are traveling to Europe this year (especially before October) there is no reason to think the price is going to drop.

I heard on Peter Greenberg's podcast (3/22/23) that due to the banking issues, demand and prices are going to be down - he suggests watch for lower fares in the next couple of weeks. He also recommends watching/buying from 330 days out if possible.

Thanks again everyone for the input. I know fares are like the stock market, but hearing everyone's experience makes it more tolerable.

I always buy 330 days out. Generally flying Tuesday thru Thursday is cheapest as the business people use up the Monday and Friday slots and the weekends are heavy travel days for working people off only on the weekend. Our business class tickets from Orlando to Milan nearly doubled in price from when we bought them to 6 months out. Same is true if using your FF miles, best deals are early and they are few in number anymore. This is the first time I am paying for airline versus using FF miles. More than half the cost of our 2 week trip is going to the airlines, painful. I will have to convince my wife to stay longer or use coach in the future.

I was just reading this today, about booking your trips earlier, from Scott Keyes (of Scott's Cheap Flights fame). Gifted article so shouldn't be behind a paywall.

You should have purchased your flights about six months ago. Suggest buying now.

To close the loop on this post. We purchased our tickets today round trip to Rome (AA ORD > FCO) and one way to Palermo (ITA FCO > PMO). We tried several different carriers, routes and applied discounts when possible and came up with the lowest price that we were comfortable with for this trip. I think getting a deal is really difficult in this environment, and it comes down to what you can stomach. We have one more leg to buy but it is regional and should be easy to book within the next few weeks.

Thank again everyone for feedback!

. We tried several different carriers, routes and applied discounts when possible

What carriers and what "discounts"?

We checked United, American, Delta, ITA Airlines, and Ryanair. My business account has discounts with United.

Last week I purchased open jaw, in to Venice out from Milan for Aug 30-September after monitoring airfare for last two months. I used google flight tracker for a while but not that helpful, then checked American Express Travel which offered some "deals". It was not encouraging. Ended up converting a stunning number of AmEx points to Delta and booking directly with Delta. Comfort plus called for 65K+ skymiles more--during a special 15% discount promotion!--than I used last year to fly to France. I was not comfortable mixing up airlines for different legs and the savings offered that way were pretty minimal. I want the airline that brought me to be obligated to get me home. (Last year's flight home cancelled and learned from that experience.) On reflecting about the increase in airfare and because I did save if I fly back mid-week (Wednesday), I decided to add 3 days in Florence and 1 extra in Venice to maximize my Italian adventure. I hope there are going to be bargains out there for others this fall, but if your dates aren't that flexible, as others have said, I would jump on what is tolerable. and I just got notice that one of the flights I was seriously considering just got cancelled!