Insuring the Trump Princess or any other luxury vessel requires customized insurance coverage, global position monitoring -- and even a dash of swashbuckling.

"There's a lot that goes along with yacht coverage," says Clement. "You have to make sure they have the proper flags flying at the right time depending upon what waters they're traveling in. Once political risk or Somali pirates come into play, they'll red-flag those areas and tell you to stay out or you won't be covered."

In addition to the craft itself, there's a crew that also may receive housing (with those attendant policies) in addition to salary, workers' compensation and disability.

"These things are floating luxury dwellings almost, with smaller craft and even helicopters attached," says Courtemanche. "There are a whole group of exposures around that."

Still, wealthy skippers who are willing to steer clear of claims can save a boatload on their yacht insurance.

"Certainly a client who would take their boat out of harm's way in hurricane season and not leave it moored in Florida would have different pricing than someone who doesn't," says Courtemanche.