Here are some notes from the 6 weeks we wound up spending in the area. Next year, we're probably going for 9 weeks, as we came back to NY too early and caught 2 snowstorms in one week back.
1- we still love Bern's. Two dinners there with above average steaks, all the other stuff they give you (I like dinner salads, onion soup, loaded baked potatoes, etc) &, most importantly very good inexpensive wines. A couple of whites, a couple of reds… details upon request. We've gone every year for about 5 years now, with friends who are obsessed and have gone every year for over 20 years (& have a copy of the original wine list book that'd fetch good money on e-Bay), and can't help but love it. Getting displaced from our table last year so that Derek Jeter could bring in his entourage was fun, but so was eating in the old room at The Grand Dame's table (no, she wasn't there).
2- E & E Stakeout Grill (yes, it's spelled that way) on Indian Rocks Rd. in Belleair Bluffs is described in one Tampa tourist mag. as "a seafood oriented steakhouse". That alone almost kept us from going, but as it is highly regarded by just about everyone, we went. And went two more times. Its a very reasonably priced place, serving better steaks than most (including a very good prime rib) in very nice rooms with very friendly service. And a limited wine list that includes some very good bottles with low mark up. Like a Jordan Cab. Sauv. for $60 (retail is usually in the $40s). Highly recommended - reservations needed.
3- Eating at the bar at Salt Rock Grill became a habit for us. Nice social place with a wide variety of choices that'll allow you to spend as little or as much as you wish & eat well prepared fresh food. I don't think it deserves a reputation as a "destination" restaurant, as they tend to add too many ingredients to their mains (sauces, spicings, conflicting sides, etc). But, it'd be as crowded in Nassau County, Long Island as it is in Indian Shores & for much the same reason. If you keep it simple you eat well. We must've been there a dozen times over the six plus weeks.
4- Fish places that we liked (because they fried things cleanly, had fresh food & were friendly… not because they were anything more than local fish shacks) included PJ's, Lola's, Crabby Bill's & The Pub. There were many more that we didn't try, but these met our need for both social lunches, informal dinners and even live music (PJ's & C.Bill's). I discovered that I love what they all call "Chicago Oysters": large gulf oysters baked with parm. cheese and butter. Usually under $12/dozen. I learned to love grouper served many ways as well.
5- We'd been to Columbia Restaurant in Ybor City and its better than the one in Sand Key, which we went to this time. The food's close to the same - in my opinion, "good" - but not quite. But the room isn't the warren of decorated rooms in Ybor City (even though its a nice view of the water, with some nice outdoor seating). The salad's great, the apps. decent and the mains fresh, if overwrought. Keeping it simple works here as well.
6- Guppy's in Indian Rocks Beach is owned by the same folks as E&E and is a good choice for a nice medium priced dinner. We went two or three times and had good salads & fish. We preferred sitting at the bar for dinner.
7-Slyce, a pizza place on Gulf in Indian Rocks Beach, has (yes, this Brooklyn guy is going to say this) good pizza. A very friendly bar area to eat at (hey, we're consistent), very good salads, good wines by the glass and bottle and pizza I can live with. And, if needed, they deliver.
If you're in Sarasota, we highly recommend the Ringling Museum, especially the circus memorabilia building. And, although I don't much like Dali, the museum in St. Pete is good & worth a visit. And, if you're a tennis player, I can recommend where to play, since we play pretty much every day and even joined Shipwatch Tennis Club while there.