I took a look now and see that it seems a lot easier to get flights from Vancouver than from Calgary, at least on Flyzoom. Hope you can work out something cheap too!

Boy, this is really getting complicated - all the different city combinations, and then the different airport combinations in London!

Mitmap

Charters, while often cheaper, can get more complicated because they don't necessarily fly every route every day of the week. This includes flyzoom.com, although I gotta admit their prices are attractive.

Simplify things by taking this in two parts: 1) YVR or Calgary to London. This will be the major part of the fare.
2)BA open jaw LGW to VCE (Venice) returning Rome FCO to - I think LHR (?) Consider taking some of the money you save and staying 1 night in a BandB near Gatwick on the outbound leg and another in a cheap hotel in Paddington (near the Heathrow Express) on the homebound journey. See a bit of London, have a chance to recouperate from the flight, and reduce your stress at the same time.

About Ryanair et al: be careful, these discount airlines offer great deals but they don't necessarily use major airports. You can use up time and money just commuting from the minor airport to where you really want to go. The flight times aren't always the greatest, either. Factor these things into your cost before deciding.

Mitmap, I forgot to mention one other thing I am looking at. Travelcuts.ca offers cheaper flights to London from both YVR and YYC with a United routing that goes through SFO to LHR. This fare is not available through the United site. For some dates I am looking at this winter, this option is $100 CAD cheaper for YVR than the cheapest Air Canada option (which is nonstop). There is the major hassle of the extra flight to SFO, but on the other hand, the flight to LHR does arrive early in the morning and you could in theory catch a flight out later that afternoon to your Italian destination.

Thanks everyone for helping out this rookie European traveller, and WillTravel, thanks so much for all your helpful resources. I've looked at all the sites mentioned, and got some good ideas for my planning. But I guess I won't be able to get a concrete idea for May pricing until the Fall.

There will probably be a seat sale for May after the fall (maybe in February or so), so I wouldn't count on the prices you seen then. However, I think these would be reasonable benchmarks:

$700-800 CAD for a charter flight to LGW
$1000-1200 CAD for an Air Canada flight to LHR
$100 CAD for any Ryanair or Easyjet flight, including public transport to the airport
$1400-1600 for a Calgary-Italy one-ticket itinerary

We did YVR to Rome two years ago. There used to be direct flights from Toront to Rome in the summer and you may wish to check and see if this is still an option. It is direct and hassle free and the luggage goes all the way through (hopefully) We did this with an open jaw return from Milan and it worked well. Air Canada was the carrier with a code share flight operated by Al Italia from Toronto. You may wish to check this option if you are not set on spending time in London.

Talexander, direct from Canada to Rome would be my preference because we want to spend our whole holiday in Italy. I'm only looking at these other options to save $. I won't bother with all these transfers if the savings is going to be less than CAD$300, but it looks like I may be able to save about a third. But I'll definitely keep my eye out for those Air Canada seat sales. How much did you pay for your open jaw ticket two years ago?

I can't tell you the cost of our flights because we used our aeroplan points, sorry.

Hi Mitmap, unfortunately Air Canada no longer does the code share to Rome with Alitalia ... the code share was dropped after the summer 2003 season ... so this is no longer an option. As a result, we have now found, for flights from Atlantic Canada, that it prices out quite a bit cheaper to fly to London on AC and then purchase a separate ticket on British Airways or Alitalia to Rome.

We are flying from Halifax to Rome in September. I have been checking flights for months on various websites. After reading this thread I called justfares.com and got the best rate by far. FYI - the website does not accept Canadian postal codes so I had to call and book in person. So- thanks for the tip.

Pius, if you don't mind my asking, how much is your ticket from justfares.com?

We paid $710 U.S. for each ticket, which translates roughly into $960 Can. This represents a saving of about $400 Can. over the cheapest fare I've seen to date. What is attractive for us, as well as the price, is that this Continental Airlines itinerary is an easy one - Halifax-Newark-Rome - with minimal stopovers and a return flight that leaves Rome not too early, 9:45 I think. Mostly it's good to have it settled so we can move ahead with the rest of the planning. This website is a Godsend.