LOL, I know about "adventures"! I have a 1970 International CO-4070A Transtar (that's a semi tractor for the curious) that was an eBay win which had sat in a farmer's field for about 25 years. I flew out and drove it back from Kansas after replacing the broken windshields and replacing 10, count 'em, TEN tires and one pair of split rims with some used one-piece wheels. Oh, and I've never driven a semi before let alone anything with a 15-speed unsynchronized transmission. It wasn't a trip, it was a journey!
Southwest does in fact fly into both Orlando and Tampa, with Orlando the nicer of the two and closer to I-95 and Tampa right off I-75. If you decide to take the plunge I'll be sure to give her a good pre-trip!