Pensacola to Miami
Checkpoints, East point, Cedar key, Sarasota, Naples, Key West, Key Largo, Miami...

I Dont know how close to 1000 miles that is, if its short by much you could always throw a leg into and out of Tampa Bay somewhere, and it'd be a great race. The tactical options in terms of routing on the west coast of Fla. add a totally different challenge versus the drag race up the east coat. Cut the corner? Stay near the beach, offshore, inshore? etc..Plus the logistics are simpler given how big the community of beach cat sailors in the start and finish areas is, and in Florida generally. It may lack some of the extreme conditions that you tend to get around hatteras, but getting to key west and then to Miami is big water and unpredictable.