Wondering if anyone could suggest the best time to buy flights for Italy this September. Any experienced travellers with any tips on beating fluctuating prices? I heard that "they" say 3 months before is often the best price available. Please feel free to send along your advice.
Unfortunately there is no rule of thumb. Just use Kayak.com and monitor periodically. There is also a feature in Kayak that tries to suggest price trends, although I'm not sure how accurate. I bought my tickets to Florence for July this year about 2 months ago. Now the same ticket (2 months from departure) is about the same I paid (maybe $10 more). Expect to pay around $900 from YYZ to FCO in Sept.
Roberto is right. We've seen posts on this Helpline on people who followed dubious advice (like "wait until 6 weeks before travel to book for best fares") and lost out on better prices. One thing to add to his reply: Prices are notably higher this year than in past years. So you can't use what people paid last year as a guide. Monitor Kayak, and the airlines flying your desired routes, every day or so. Keep your credit card and passport information handy (you have to book the ticket in the exact same name as your passport). Then, when you see a sale, you'll know it's a good deal and be ready to pounce. Then, don't look back.
I've had good luck with Orbitz too, and on my last trip I happened to be looking late one Friday night and found a good fare, then saved a bit more by booking directly with the airline (American). I just set a price in my head that I'm willing to pay ($1,100 from Seattle to FCO in May for instance) and when I see that, I buy it. Otherwise I drive myself crazy wondering if I should wait. Good luck!