Customs will allow it. You need to check in to Canadian customs when you touch shore there, then clear customs in US when you return- you can do this by videophone at several locations (one in the islands) but it's a nuisance. Otherwise get an I-68 for everyone on board and you can clear US customs by cellphone. On the way from the islands back to Cleveland recommend a stop in Vermilion. Some public docks there and a 5 star French restaurant overlooking the public docks.
1977 C&C 30 Mk 1 hailing from Port Clinton, Ohio