One piece of hard-won wisdom before you start: your first boat probably will not be your last, there is no such thing as the perfect boat, and every used boat is a compromise. A broker — for serious or first-time buyers, a broker weeds out bad options and arranges surveys, sea trials, and paperwork. Boat Buying FAQDo I really need a survey if I’m paying cash? What does a boat survey actually check? Why is boat insurance so expensive in the Caribbean?