Unfortunately they don't have a good listing of upcoming fittings. Probably a good reason for it. I know the fitter I used has a full time job and has to arrange when he can do it. If you sign up for updates you will usually get notified as they come close. Another option is to visit some of the courses and ask about Titleist fitters. You can sometimes get their name and contact info, and they can give you an idea on what's coming up.

Correct, there is nothing scheduled within 50 miles of Orlando now.
Keep checking the Club Fittings tab on the website. Living in the Upper Midwest, it sure is warm enough for me there. Not sure why Orlando doesn’t have events, yet. Something should start to appear by the end of the PGA Florida swing.

Make the drive to see John Dal Santo in Naples... he's one of the best fitters in the country. He has a tour-level fitting bay, but you can test outdoors as well. He can be booked via Titleist website, he does fittings at Mediterra CC a few times a month during season.