The Carnet is a little more expensive but usually pays for itself in the long run, especially if you are going to be in North America for a while going in and out of Canada and the US.
The best thing about a Carnet: You can land in one country, and ship back from another.
Example: Land in Montreal or Halifax, and it could leave via a US port.
Example: come to Canada for training and regattas in July and August, and later sail in Florida midwinters, shipping out from there.
Plan to load a trailer into the container if you are going to make this kind of trip.
The EU is much easier to cross borders. Canada and the US are very distinct entities in this way. It's not all just "North America".
Don't forget paperwork for your coach boat if you are also bringing one of those.
Have your Broker do the Carnet and/or temporary import bond.
This will save enormous time and energy. Avoid doing this paperwork if at all possible. It can be annoyingly technical. If you like a challenge then do this part yourself.
If you get a Carnet. Don't lose it. It is like a passport for your boat. You can't get it home without it. Bringing your boat home without a Carnet is like claiming refugee status - very difficult.
If your container is travelling by ship, and landing in a Canadian port, there are three options.
You could ship to a US port. Boston, 690 km away, for example.
Decide where to unload your container. You can do this at the port, at a more local depot, or at the Yacht Club or sailing venue.
If you have a trailer anyway, it may make sense to unload immediately at the port where the container arrives in Canada. Sometimes a 200 km truck delivery is the same price as unloading it yourself because of Union rules.
Container loading and unloading can also be easy by doing it at a depot. They have the cranes there, and all loading and unloading happens while the Container is at ground level.
If the container comes to Kingston
You can have your container delivered to Portsmouth Olympic Harbour. That's often ideal, teams do it all the time, and it's great if you have lots of gear. Downsides: container handling is costlier. You need to hire a crane to take your Container off the truck.
Another place to send and/or unload containers in Kingston:
DC Marine Ltd.
785 Sir John A. MacDonald
Kingston, Ontario
Tel. 613-544-5626
They have a ramp where a truck can back up, and the container can be be unloaded without taking the container off the truck.
This is especially useful for Coach boats which are too heavy to lift in and out of a container.
Most dinghies can be loaded and unloaded with muscle power.
The EU is much easier to cross borders. Canada and the US are very distinct entities. "North America" is not like "Europe". Have your act pulled-together, and in order, if you cross borders here.