if you are going Caribbean St Thomas is the place!! Puerto Rico, to me, is great for a port call on a cruise. I was not impressed. Meanwhile St Thomas is the only island/city that I was actually excited to go shopping in my entire life. Beautiful island, great shopping, wonderful beaches. To me, Virgin Islands is the place to go..
I have lived in SW Fl. FT Myers/Naples and Sfla FTL/ Miami. Beach and water (to me) is much better on the ocean side. Naples has nice beach and people are much nicer (since they are mostly from the midwest) but not as much nightlife and food variety. My suggestion is Siesta Key near Sarasota if you are doing FL..