Since our homeport is St. Pete, I think I can offer you some thoughts that might prove useful...
First, the Bay is a great place to start your sailing adventures. Great weather almost always. When you want to begin stretching yourselves, good nearby cruising on the Bay, and then S along the protect ICW (for starters
, right up the Manatee River, just past the Skyway). Multiple ''cuts'' that will allow you to sample sailing on the Gulf. And even an overnight anchorage in Vinoy Basin by the St. Pete Pier is great fun - might even get a free concert as a bonus!
For reasons such as these, I recommend locating the eventual boat on the Bay side vs. along the Boca Ciega Bay/ICW strip from St. Pete Beach to Clearwater...but I realize others might see it differently, as those waters also have their attractions. Your own location will also discount some places.
As for a starting place, turn off the computer, put down the magazines and - both of you - get engaged! Nothing beats actual ''doing'' and you''ve got lots of options: look for local boat clubs where you can perhaps get a lesson or rent a boat; enroll in the low-cost USCG and/or Power Squadron courses (both available all over Tampa Bay), which not only will give you some basic training but also intro you to other sailors, a big plus; walk the docks & talk to folks - ask around for perhaps a short-handed boat that would like to trade a scrubbed deck for an afternoon sail; call the local Comm Colleges to see what facilities exist for students, since you can enroll just like the young kids (SPJC has a wonderful sailing facility right across from the Harborage & it''s ''big boats'').
There are lots of good ways to get started; the key is to get your hands dirty & feet wet. You''ll soon find out whether this sailing bug is for you, and better for you & your pocketbook you learn sooner than later.
FWIW our first experience, out of shear curiosity like yours, was to ''charter'' (fancy word for ''rent'') a boat along with some friends - and her captain - for a sail & anchoring overnight at a nearby island. What a great way to begin seeing/feeling what this was all about. Our next step was to take vacation time & and enroll in another owner-operated Cal 34 for a week''s cruising/sailing instruction. What wonderful dumb luck! The USCG retired owner offered structured training, right from the basics, while we sailed each day to a different anchorage & spent the night. We left that week''s experience with real if also carefully supervised cruising under our belts. Great stuff. To those who might question the cost, it was outstanding ''value'' and helped us over the hurdle of ''Is buying a boat really sensible, financially?'' We knew enough to know we liked what we''d seen & done.
Involvement might seem awkward & difficult from the remote sidelines...but that doesn''t last long. Start getting involved, and you''ll soon know if this really is for you. And good luck!