I've never lived in SW FL, just spent a lot of time there. I don't see a reason to drive all the way up to Tampa Bay - not sure what TPA has to offer that Naples/Fort Myers doesn't, and when you add in Sarasota, then it's game over. Boutiques on 5th (blocks upon blocks of boutiques, antiques, restaurants, etc), Waterside Shoppes (upscale shoppes anchored by Saks and Nordstrom), Coconut Point (basically exactly like SJTC and anchored by Dillards), all the outlets (Miromar, Tanger, Naples), and the mall in Fort Myers (Dillards, Macy's, JCP, etc). The only thing so far as I can tell that Tampa has that SW FL doesn't is a Neiman Marcus, and there is a Last Call at Miromar Outlets. My point of reference is that one of my best friend's parents moved down to Bonita Bay, so we would visit frequently. Get off at Corkscrew and pass Miromar and Coconut Point on the way. My mother's childhood friends all live down there now; one is one of the developers of Pelican Bay in Naples and other major sites.

The ladies in my family love shopping down there!
edit: forgot to mention the obvious - if it ain't in SW FL, South Florida is a shorter, less congested drive away than Tampa!!

SoFla has the best shopping in the country outside of NYC, LA and SF, hands down.