This is actually an extremely specific request, which I’m not sure holds a definite answer.

Regarding your first assumption, “raid” seemingly did not begin as a French concept at all, instead coming from Scottish attacks on the English. The ATILF states:

1.1864 « incursion rapide en territoire ennemi » ici, aux États-Unis (L’Illustration, 13 août, 102a ds HÖFLER Anglic.);

2. 1886 sports (La Revue vélocipédique, 1er oct., 149b ds HÖFLER Anglic.). Empr. à l’angl. raid « expédition militaire à cheval » (1425 ds NED) d’où « incursion, charge » (surtout des Écossais en Angleterre), empr. à la forme écossaise du vieil angl. rád d’où est issu l’angl. road « chevauchée, voyage à cheval » puis « route ».

Now, for a boat-centric perspective, you’d need the help of a French leisure/sport-boat historian, if there is such a thing. But in any case it is safe to assume that it is a derivation from the “sports raid” that you mentioned, which is already quite old itself, and usually conveys the meaning of “endurance” (of both men and hardware). If the boat raid often has this meaning, then it’s very likely that it’s just taken from the sports raids of old.

The “small boat raid” notion is not very publicized in France (unless you’re talking about kayaks), and even famous bigger-boat raids are not necessarily known as “raids” but rather “courses”, “transats” or “routes” (eg. Route du Rhum, Transat Jacques-Vabre, Vendée-Globe, etc). Nowadays, to a Frenchman, a “raid” can either marginally mean a car race like the Paris-Dakar or the 4L Trophy, or more commonly refer to non-motorized sport activities (hikes, the aforementioned canoes-kayaks, running trails, swimming, etc.)

I’m not sure I’ve been very helpful but hopefully you got some clues out of this 🙂