You sure could. I'd mostly buy nice preowned/used boats, to save room for a few more:
I would absolutely buy/order a new 46 Skater to keep in Florida. Merc 1350's obviously, & totally tricked out otherwise. Poker Runs, regular runs to the Keys, Bahamas, etc, would be it's primary occupation. Est: $8-900k insured.
I would buy one of the preowned 46 Cigarettes on the market, & have everything freshened up to my liking. It would stay in Florida with the Skater, for days we wanted downstairs room and speed. Est: $500k total, after freshening.
I'd buy a clean preowned Intrepid fishing boat. Est: $2-300k insured.
I'd buy a sweet preowned 45-60ft Pershing, Magnum, or similar performance yacht, for island, key, & bar hopping with the fellas & bikinis. Est: around $2-3 million docked & insured.
I'd buy a ridiculously tricked out pontoon boat, for here at the lake on days we don't want to mess with the 368 I would keep. Est: $50k beached & carrying liability.
Roughly $4.7 spent, so the remaining balance would cover a little fuel. My friends can buy the drinks
Those would keep me busy for awhile.