Originally Posted by
PWMTrav
It sounds like you might be a little new to using points. Here's how I'd suggest going about this -
First, do some googling for the best programs in terms of value, but from Amex I'd suggest starting with Flying Blue and Aeroplan if you want a good starting point. Don't transfer anything yet. Just go to their sites and start searching for dates and itineraries that work for you. If you find something that does, that's when you transfer your points (both programs should transfer instantly) and immediately book.
FlyingBlue is your best bet from here, if I had to guess. Their award pricing is dynamic, and 55k points is about the lowest you'll find one way in business class from the west coast to Europe - but August is tough, that's peak of peak and you might need to burn some additional points. But since FB is dynamic, something will be available, you'll just have to decide whether it's worth it over cash fares. You'll almost certainly connect in CDG or AMS and can get to most places in Italy with 1 stop. Obviously you'll just have to search for whatever airports you're willing to fly into in Italy.
Aeroplan is going to be dynamic pricing for Air Canada flights and they're basically never a good value. You're shopping for partner flights there - from the west coast, it's going to be Lufthansa, Swiss, or United most of the time, with Lufthansa usually being where I find my availability. But it'll be a lot tighter than Air France in terms of space.
You should search often. It may take some persistence to find the flights/prices you want - and in August, they may simply never materialize, but you should spend some time each day searching if you really want to maximize your odds. 4 seats will be especially challenging.
There are obviously other programs that Amex transfers into. You'll have to do your research there on their airline partners, pricing, and availability. The two programs above are almost always what I book out of, though, and Air France more often than Aeroplan. If you can make the drive, YVR tends to be a bit easier to find availability for me vs SEA. You can also search out of SFO and LAX if you're willing to book a separate paid flight down to one of those (or get lucky and find the connecting segment available).
Appreciate the great response. YVR is a bit closer to me than SEA. My initial search tells me Air France is probably going to be the way to go.