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Jacksonville has hands down the worst, followed by Tampa. Those are truly two of the least vibrant downtowns in the country. St. Pete downtown actually has some good bones and a few pretty good restaurants, bars, etc..
Orlando gets my vote as the downtown core has improved considerably. Lake Eola is great, especially on the weekends with the farmers markets and food stands. Church street seems to be making a reemergence and finally is not strictly a club district, but combining a growing local restaurant scene (Not the disgusting chain restaurants that have long dominated Orlando), cocktail bars and condo's. You can finally live, work and play in Downtown Orlando. Also it doesn't hurt that Little Saigon is growing by the month off Colonial and is a great place to eat and shop for groceries. Not saying its a top tier DT by any stretch, but it has potential and the best of the bunch on this list.
When it comes to being visually attractive, Saint Petersburg is more appealing at the core than all three. OTOH, Tampa's very few core blocks and a few of Jacksonville's core neighborhoods have more visual appeal than Orlando's core neighborhoods. But Orlando's downtown looks better than Tampa's and Jacksonville's downtown.
Depends what is the "urban core." If we're speaking strictly of downtown then I think Orlando and St Pete are best, each in a different way. If you are talking about all the urban core neighborhoods then Jax has a fighting chance. Actually perhaps it's the best, but I'm not too familiar with their counterparts in Orlando and Tampa. But that's really stretching the urban core out to a 3-mile radius around downtown.
St.Pete has alot of character in it's core, and in adjacent neighborhoods. It's amazing the number of Historic neighborhoods and Historic homes St.Pete has preserved. Same could be said of Tampa. Old West Tampa still has that old Cuban neighborhood feel. There are still old cigar factories and old breweries in business.
Orlando... then St Pete ( which I hear is about to boom), then Tampa, then easily the worst is Jacksonville which apparently had amazing bones but now looks like the Southeast US version of Detroit.
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