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The short answer: YES, but you need a captain (two people) ideally with a valid US work permit to do so.
For the moment, American customs still authorize this kind of trip every Wednesday in September (2021).
Except that the CRUISING PERMIT is still impossible for a Canadian boater to obtain since the (land) border is closed for non-essentials. But air travel is (difficult to understand this logic).
So, yes, the boat can cross the border, but with restrictions. For example, you can have your boat transported by water to Florida, but with a commercial crew since you cannot obtain a Cruising Permit.
You can still get to your boat by plane, but applying for a Cruising Permit remains problematic for an owner-owned Canadian boater.
This is the information we have, but it is very variable and subject to change without notice ...
Hopefully for September 21, 2021, things will evolve favorably for boaters.
By land transport on a trailer, yes if you call on a transporter specialized in this domain.
Click here for a partial list.
To be followed closely.