Simeon,
What type of phone do you have and is it unlocked? Also are you on a PAYG account or a monthly pay account?
You might want to phone Freedom Mobile / WIND to get the details on their international roaming accounts. If that option is available to you, it will likely be the easiest and simplest way to go.
I'm with Rogers and have been using their Roam Like Home plan for the last few years and although it's expensive, it really works well. I tend to keep the cellular data "off" as much as possible and use the Wi-Fi in hotels. That's important so that I don't exceed the data limit.