The Florida resort tourist town of "Citrus Cove" featured in the film is fictitious and does not really exist in real life. The sign for this fictitious town which is actually located right before the "Johns Pass Bridge" on Madeira Beach.
The make and model of the Chester family car which trailered a U-Haul, according to the IMCDb, was a creme-top brown-body 1979 Oldsmobile Ninety-Eight Luxury sedan.
When the Barnacle is gaining on the other sailboats, you can clearly see a water jet from the starboard (right) side of the boat, which indicates the engine is running, even though the boat is supposedly under sail.
When the regatta race begins, the shots on the Barnacle change to Laurie asking Sandy: "Mommy can I play in the basement with Yorku"? The voice however is not of Laurie, but instead is Jennifer making a young child voice.
During the race, Jack says the sailboat in front of them has 'stolen their wind'. Technically, that is a racing term for someone BEHIND you who has gotten between the wind and your sail, effectively blocking your wind. It's also a racing strategy. But it is impossible for someone to steal your wind from in front of you.