The boat sails good in the gulf. If you are renting one it will handle anything they will let you take it out in, most rental operators have a cut off limit. I've sailed it in probably 4 four surf and it does okay. It is kinda short so surfing isn't its best point but as long as you know how to sail in surf it is manageable. We see how many times in a row you can flip and get it back up w/o getting wet, hope that answers your question about how easy it is to get back up. I have not put one on top of a car but it rides nice in the back of a full size truck, even with a truck box! What part of the Gulf are you going to visit?
Authorized Hobie/Vanguard Dealer
Division 15 Chairman
Panama City Beach, FL