SHORT ANSWER: To import a motorcycle to Canada from USA from time of purchase to time you can ride in Canada will require a little paperwork, due dilligence on your part to make sure paperwork is being processed correctly and on time, a trip to get your bike and then registering your bike in Canada. The time from purchase to final registration can be as fast as 1 week, or as long as 2 or 3 weeks worst case scenario. You will have to agree to buy the bike up front from a seller over the phone or by email, make sure there are no liens and that all safety recalls have been cleared on the bike, buy it via wire transfer or bank draft, then have the appropriate paperwork faxed to a border crossing, have a 72 hour wait, you call the border to make sure your paperwork is cleared, you can arrange for insurance on your motorcycle before you go, then you make a trip to the USA to get the motorcycle and take it back, the dealer can give you some temporary registration for riding in the USA optionally, there's some paperwork that you present and fill out at the border, you pay the sales tax of your province of residence (HST, PST or GST depending on where you live) and a $200 fee for inspection by Canadian Tire. If you are buying from Washington and you live in BC they may also charge you Washington sales tax if buying from a dealership. Once in Canada you will fax a form to RIV Canada, wait about a week or less, get a form back, arrange to get the motorcycle inspected by Canadian Tire and get that done, then go and register the bike.
STEP-BY-STEP LONG ANSWER: Transport Canada's website directs people to look at the Registrar of Imported Vehicles (RIV) website for the procedure. You should read this too just to double check everything, procedures might have changed since 2011, but below I will give more detail and tips from an experience standpoint.
1. Check that the vehicle you want to import is on the RIV Admissibility list. The PDF list link seems to work best on this website. If it is not on the list, you will probably not be able to import it. Section 8 on the list is for motorcycles. Also check how to convert the speedometer to metric (Kph), you'll want to make sure you can do this before the Canadian Tire RIV inspection. All vehicles on this list should likely have this ability, on bikes it's usually a button combination you push on the handlebars or HUD menus. For example, hold button A while turning ignition key, navigate menus with buttons A and B, select CAN ... etc. Note, that I have found that at the Canadian Tire inspections I've witnessed, the inspector is lazy and never checked the speedometer. So if you don't switch it, I wouldn't worry about it.
2. You will be exempt from duty fees at the border if you buy a motorcycle that is "assembled in the USA" or built in the USA, and maximize your savings. Surprisingly, I am finding that most if not all Japanese and Italian motorcycles are assembled in the USA such as Ducati and Honda, so they are exempt. Also it will be in your best interest to buy from a US state that has no sales taxes and is ideally close to Canada, distance wise. Oregon, Montana, New Hampshire, Alaska and Delaware are the ones, last time I checked. I have had good success with Oregon. Interestingly, I purchased the CBR1000RR from a dealer in Washington, and even though Washington has a sales tax, they did NOT CHARGE ME it. So if you want to buy from a state that has sales tax you may just be able to get away without paying any. You should phone the dealership you are buying from to confirm. If you are lucky and reside in a province that has only GST and no HST or PST, you will pay just the GST. If you live in a province with HST or PST you have to pay those when crossing the border. Details can be found in the FAQ section at the RIV website here. There is one last thing to be careful of. If you are importing from Washington into BC (or perhaps other states as well), the dealership may be required to charge you an extra fee on top of your purchase price, I believe they are required to charge you Washington sales tax. I'm not 100% sure of the details, you should phone the dealer to find out. I do know, that if you import from Washington into Alberta that you do NOT have to pay their sales tax. I advise that you call up the dealership you are buying from and ask them if there are additional taxes or tax exemptions based on which province you reside in. I have heard that residents of Alberta, Saskatchewan and Manitoba are all exempt from paying Washington sales tax. In my case, crossing at Eastport/Kingsgate (BC crossing), and being a resident of Alberta, and purchasing a bike from Washington, I did not have to pay Washington sales tax because I am a resident of Alberta, and I did not have to pay HST even though I used a BC border crossing, I only paid GST and the RIV fee being an Alberta resident.
3. Research and buy. Generally I trust dealerships in the USA rather than buying from a private seller. If the bike is used, ask for the VIN number from the dealership and run history check on the VIN, it costs about $30 through sites like AutoCheck or CARFAX. You want to make sure it has a clean history, or know about any accidents that the bike might have been in. The reason is dealerships you can do a background check really easy and see them on Google Street View, get their address and phone number. So it would be difficult for a dealership to steal your money and not give you a motorcycle. On the other hand, a private sale is more risky because somebody could be posting a motorcycle up as a scam artist. So I advise people buy from dealerships, new or used for this reason. I have had good success finding used motorcycles sold by dealerships through Cycle Trader website, which is very similar to Auto Trader. Make sure the dealer shows you lots of photos of the bike, and tells you everything about it, like damage, mileage etc. Generally I've found that negotiation on price isn't really effective when buying from a dealer in the USA, unless that dealer is going to have a really tough time selling a particular bike. If there is a high demand, even be prepared to pay additional freight and PDI fees. A wire transfer of the money through your bank, or sending the dealer a bank draft or money order are the most common ways to send the money. I have done both, and I recommend that you just send a money order in US funds to the dealer. I had some issues with my wire transfer, and wire transfers are prone to failure, and the number of days for a wire transfer to get through is about the same number of days sending an envelope 2-3 days delivery. Also wire transfers cost MORE to send than a money order! I think a wire transfer fee is about $30, but it only costs about $8 for a money order and perhaps $10 for fast mail service. So I highly recommend you just send a money order to the dealer, you'll save time, money, and complication. Also check and see what your bank is charging for the percentage fee they are taking over and above the US->CAD conversion rate. I found that anything less than 2% is normal, ideally you should see if they will do 1.5% or better but that's probably out of your control. Also might be worth trying to buy the motorcycle with a credit card with cash-back rewards. I have not been able to do this as of yet because I think most dealerships don't allow credit cards for such large purchases due to large fees they would have to pay to MasterCard/Visa etc, but with some credit cards that take 2.5% commission , a 1% cash back rewards card would end up only taking 1.5% which is probably 0.5% better than your local bank's conversion rate when making out the money order. If you use a credit card find out exactly what cut they take on foreign exchange. The best credit cards take 2.5%, the worst I have seen as high as 4% which is unacceptable. CapitalOne MasterCard and most VISA cards tend to have 2.5%.
4. Select which border crossing you will want to cross at. Be sure that this crossing will be open for import/exports at the time and day you expect to cross. You should call them up to make sure. RIV Canada's website gives you the contact numbers here. Also instead of using the internet, you should call up the US side of the border crossing you want to import your vehicle through, and ask them for the fax number that you will fax the "Worksheet" to 72 hours (working days) in advance prior to export. The fax number likely will NOT be the fax number for that border crossing. For example last time I crossed through Sweetgrass, I had to first fax my paperwork to Whitlash crossing 72 hours in advance.
5. Paperwork: 72 hours working days in advance, you will fax a "Worksheet", a bill of sale (BOTH SIDES with signiture of release on the back), or if the motorcycle is brand new you will fax a Certificate of Origin (both sides). I have provided this worksheet hosted on my website because I had difficulty and could not find it on the CBP website today, I advise that you call up the border and ask them to fax you the most current worksheet just in case it has changed, this one is from 2007. You will need these sent to you from the dealership. Do not trust the dealership to properly do your paperwork. I learned this the hard way, if they forget to fax BOTH SIDES of the bill of sale, or title, along with a PROPERLY filled out "worksheet", this is bad news and could cost you up to 3 more days of waiting with a bike on your trailer, in the USA. It happened to me, but I was lucky it was cleared up in just 1 extra day. It is also difficult to call up and find out if your paperwork was complete or not, so get it right the first time. While you're at it, you should get some recall clearance. You can get it in one of 3 ways. 1. Get the dealership to send you a formal letter with company letterhead and signed or stamped, stating that the motorcycle is free from all factory safety recalls and that all recall work has been performed on the bike. OR 2. Instead of the letter, just have the dealer provide you with a printout from the motorcycle manufacturer service computer system that states all recall work has been completed, this is a database screen shot showing the VIN number, make, model, recall clearance, and work done YES or NO and it is one page long. If the dealer does not want to give you this, most authorized motorcycle repair shops will be happy to email you a screen shot from their database for free. You will not need this until AFTER you get back into Canada but it's best to get it as soon as you can.
6. See if you can get insurance on the motorcycle before it gets into Canada, for the Canadian side. You don't actually need any insurance if you are not riding the bike back, they do not check it when you cross the border, the only reasons you might want insurance is if you are riding it for any period of time on the way back or if you are concerned of theft or damage when you are brining it back. I've had great success with State Farm. With a clean record they also have excellent insurance rates, however they require you to have your car insured through them which can be expensive. Also inquire with the dealer if they can set you up with temporary registration for riding the motorcycle while you're in the USA, particularly if you're riding it back. Contact the DMV directly to get the temp registration if the dealer will not help you.
7. After 72 hours on working days, call the border crossing to determine if your paperwork is cleared. This is very important, because if your paperwork was incomplete, you need to know this and to re-submit it and wait up to an additional 72 hours for the completed paperwork to be cleared. Sometimes they are quicker than this though but don't bet on it.
8. Go to the USA and get your bike! At the dealership: Get the ORIGINAL receipt with cost breakdown (add-on parts, freight and PDI). At the border they will want to know the value of the bike, not the freight and PDI or other things. Also at the dealership get the ORIGINAL title and/or bill of sale, and have you and the dealership fill out the transfer of ownership sections on the back of the Title. You may also need to fill out an affidavit form that waives you from paying state tax, that the dealer provides for you. Get the bike. My advice is to bring a good LONG ramp to load your bike up (with short ramps, motorcycles will often bottom-out on the edge of your truck box or trailer), and PULL STRAPS and a Canyon Dancer harness. Use at least 4 pull straps, one on each side of handle bars, and one on each rear foot peg bulling at an angle rearward, or other secure locations. Be sure to partly compress the front forks when you are tightening the front straps so the bike is rigid but don't compress too much or you may damage your fork seals. Periodically check the straps as you are coming home for tightness. It helps to have a wheel chock in the trailer or truck box too. There are videos on youtube how to load and secure a bike.
9. If you spend more than 48 hours in the USA you will get a GST exemption (refund) of 0.05 x $400 = $20 discount when you go to pay the GST later for the bike at the border. If you spend more days, I think the next is a $750 x 0.05 = $37.50 after 7 days time.
10. Border. At the US side of the border, present the bike and your bill of sale / certificate of origin and original receipt with cost breakdown (all original copies) and your ID / passport. They will likely give you a stamp and have you go to the Canadian side of the crossing. At the Canadian side and if you are an Alberta resident, they charge you just the GST minus the exemption fee (0.05x$400 for 48 hours in the USA for example), and charge you a $200 RIV canada fee, which pays for RIV to do a background check on your bike soon, and pays for Canadian Tire to do the import inspection soon. If you reside in a province with HST or PST you pay those. Hopefully they will not try and charge you any duty fees, for example, if the motorcycle was assembled outside of the USA. At the Canadian side they give you "Form 1" that you fill out while you are there. This is a very important paper. They will not fax it anywhere, this is your responsibility...
11. Take your bike home, and fax (or email) your "Form 1" PLUS the factory recall clearance letter PLUS the recall clearance system printout to RIV Canada. I think the letter is optional, but the system printout from the manufacturer is required.
12. Call RIV Canada periodically or check the status of your application using their online system. When your recall has passed, request from them to email you the "Form 2". RIV Canada will likely take about a week complete their investigation before sending you Form 2.
13. Take your bike and "Form 2" to an authorized Canadian Tire to do the inspection. This is required for new or used vehicles. Canadian Tire will not do an inspection without Form 2. Call ahead to make sure the CDN Tire you select does inspections. Be sure you changed your odometer so that it reads in kilometers and not miles prior to going to Canadian Tire. However, note that a lot of Canadian Tires won't even bother to turn on the ignition of your bike, all they will do is just check to make sure you have the original emissions EPA stickers on the frame of the bike, and check that the VIN number on the frame of the bike matches the VIN on Form 2. It takes like 1 minute for the entire inspection.
14. Register. Canadian tire will give you another form saying you passed the inspection. Present your Form 2, bill of sale or certificate of origin, ID, and any other paperwork they ask for at a registry office, and they will register your bike. You can ride now! You're done! Please comment below if I've made any mistakes, or if you have any questions and I'll be sure to add or modify.