Hoping to take a trip to France and Italy late next summer. Dates are fairly flexible, but thinking about 14-16 nights, and need to return by September 8. Choking on fares posted on Kayak around those dates, but concerned that if I wait too long, I'll have problems with land arrangements. Advice?

I like to use itasoftware's month long search to track prices. I booked my September ticket in May, but that was before the economy imploded and gas skyrocketed.

You will be traveling when Europe is on vacation, but it would really depend on where you are going in France/Italy. I found the hilltowns in Tuscany quite deserted in mid-September even though it was supposed to be high season.

The only good fares I have seen have been with Air Berlin for summer. I would wait.

I would wait. I often see good deals pop up on Northwest/KLM, AA, and Continental in the 1-1/2 to 3 month out time frame.

If you're worried about "land arrangements" (presumably, you mean hotel bookings among other things), you can always make some cancellable arrangements now and then monitor prices. Make hotel bookings that straddle the dates you expect to be somewhere; usually, you can amend reservations for a shorter period of time without having to pay a higher rate (e.g. if hotel prices jump because demand surges). You don't necessarily need to make all your hotel bookings - just those where you expect rates might skyrocket or availability might dry up. For example, if you think you want to go to Venice for 4 nights during your trip, you could make a couple of bookings at your favoured hotel for different dates, and then cancel most of the bookings once you book your airfare.