Tampa downtown has some museums & channel side eateries, Also YBOR city, which is adjacent to channel side in the south Tampa area ( where the big buildings are). There is a tram that will take you there for a small fee right by the convention center & the large channel side Marriott. It can be fun at night ( wild Clubs, Food, cigars, bars) & also has the original Columbia restaurant there.
Heading south stop at St Petersburg. Head to the downtown area on the south eastern tip. It has the Dali museum (5th ave South right on the waters edge) which has one of the greatest collections outside of Barcelona Spain, if your into that. Walk North along Bayshore drive towards the pier, plenty of food & scenery. the Moon under water restaurant is one of my favorite places they serve English style food (Beef Flakey was great) within the menu. St Pete used to have a Cold war exhibit that was really cool within walking distance. Head over to the west side & visit St Pete beach. Its a great beach area & stop at the Undertow bar, have a few & look onto the Gulf, really nice view especially from the top deck.
Heading south stop in Sarasota. It has the Wringling museum & estate , worth a visit than go over the short bridge to St Armands circle in Lido key for some really nice food. Siesta key is nice to visit on the way down south & check out the town of Venice, beautiful spots in that area. Port Charlotte has a nice area for sidewalk dining & touring shops.
Ft. Myers has the Edison & Henry Ford estates, really worth the trip. Than head over to Sanibel island which is popular for shell collectors.
Than south to Naples/ Marco island for some of the best beaches that Fl has. If you like fishing than you will be in paradise. If you want to explore further south I think there is a Ferry that will take you from Naples over to Key West. I know Ft Myers has one but that is further north, just a thought.
Enjoy the trip.
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