my guess is that it will not, but I really don't know. At the very least you should run a comprehensive background check on yourself to see what comes up. I promise you - it is very likely that they will ask if you've ever been arrested. The last time I was there (in September) not only did they ask if I've ever been arrested and/or convicted (no, I haven't), they also asked if I've ever even been accused of anything. Both the Canadians and the Americans searched me and my car at the border; if I had significantly more money entering America than I did entering Canada, it would have raised LOTS of red flags at the American border. The Americans and Canadians share a computer database, and they can see everything that is recorded at each border crossing. And yes, the previous poster is correct - it's not illegal to carry more than $10,000 cash if you declare it, but I promise you - if they suspect that the money was obtained illegally, you will be detained and questioned for HOURS, at the very least, and you better have a pretty good explanation as to where the money came from if you expect to be let go. It is a very scary experience, and just because you technically *should be able to* carry the money, doesn't mean you *should* carry the money. Hell, technically, as an American citizen, you don't *have* to answer the American border guards questions (5th Amendment applies), but if you ever hope to travel outside the country again (ie, if you hope not to be flagged in the computer system), it's a good idea to play nice with them.
When you cross the border, you need to be prepared to tell the border guards why you're going, where you'll be staying and how long you'll be staying. They want to have a reasonable amount of evidence that you'll leave when you say you will (do you have a job, home and/or family in the US? or do you have a round trip airline ticket, for example), and you need evidence that you have enough money to support yourself while you're there (and obviously you will NOT be able to claim that you will make money as you go). A very general rule of thumb is that they like to see is $300 per day of visitation, unless you have evidence that someone else (family, friend or business) is going to provide room and board for you; in that case, you still have to prove you have access to funds, but you don't need as much. In the past, I have had to show them my cash on hand, and if you don't have cash, they sometimes ask for proof of bank balances and/or credit limits. I also carry a notarized "letter of invitation" from a Canadian citizen which states that my room and board is covered while I'm there.
The guards have an enormous amount of discretion in deciding who to allow in, and they can deny you based on nothing more than their "gut feeling" that something is not on the up and up. You will have a hard time getting in if you just go and say you want to travel around the country with no real itinerary and no proof that you're able to support yourself during that time.
And in response to one of the other answers to your question: just because you have a passport does not mean you're eligible to enter. Your passport is issued by the US government; the Canadians decide their own rules for themselves.
Do google searches on other American's issues entering Canada, and you will be amazed at what you find. People with pot busts from the 1970s have been turned away at the border in the 2000s. Until 2001 Americans were able to enter Canada with little more than a wave to the border guards, and we got used to it. 9-11 changed everything. Technically the Canadian rules haven't changed - even before 9-11, Americans with criminal convictions were not SUPPOSED to be able to enter, but they never bothered to actually check and enforce the rules. But now the technology makes it incredibly easy to check you out, and they do.
Again it is *possible* that you will have none of these problems, depending on the border guard you get. And I'm sure there are people reading this who will tell you that I'm raising unnecessary concerns just because they didn't have any issues; however, if it's been more than 3 years since they traveled there, their experience is irrelevant due to upgrades in the computer system used by both countries - it is much easier for the border guards to check you out now than it used to be. And in recent years, they have significantly stepped up their enforcement of the rules, and you definitely need to be prepared.
but I have to confess, your experiences mirror.
The only suggestion I might add about carrying cash and having an explanation for it is to use casino gambling as an excuse. Even then they may grill you for what seems like forever, but it is a valid reason for carrying cash and almost impossible to disprove.
I have no idea why the Canadian border is such a bitch to cross, but it is the toughest country to enter or leave in our hemisphere bar none, I have had an easier time leaving Bogota Colombia still dead drunk from the night before than I do a routing business trip to Canada.
One other word of advice about Canada, NEVER admit traveling there on business if there is anyway to explain your presence there for any other reason. My first post 9-11 visit to Toronto on business was marred by spending well over an hour explaining to a clueless woman why one oil company would want to have a meeting with another company in the same business. Since then, I always claim to either be fishing, or gambling. Of course this only works for short trips, it would be hard to explain a 90 day trip that way. lol
and yes, I only WISH that you were raising unnecessary concerns, traveling to Canada can be a bitch. They take their jobs very, very seriously.
