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My wife and I will be in Clearwater goofing off for 3 days and Orlando for business after that. We've never been to Florida before. Without sounding to lame, I always like to see the locals, or know where the hang. I'm a Hobie Power Skiff nut. Just bought my second one...picture here in Mexico...:)
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If you're going to be in Clearwater but want to get some local flavor head a bit north to Dunedin, Safety Harbor, or Tarpon Springs. All three areas have nice little communities, restaurants or bars, weekly festivals, etc. The vibe is WAY more local than Clearwater.

Grab a meal at Bar Fly in Safety Harbor...live music, bloody mary bar, walking distance from the bay...
http://www.barflysafetyharbor.com/

Best fresh fish I've had in my life was the lionfish at Black Pearl in Dunedin...
http://www.theblackpearldunedin.com/

Visit the sponge docks (admittedly kinda touristy) and eat Greek food in Tarpon Springs...
https://spongedocks.net/
 

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Dunedin is fantastic with a nice walkable downtown area. If you like Greek food, Tarpon Springs is the closet to a Greek community one can get without visiting it directly.
 

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Thanks for all that guys. My wife is plugging in the locations. It's 24º and freezing rain today here. We are really looking forward to visiting Florida!
 

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If you want to take a drive and see what Florida used to look like, head north to the Crystal River area and even all the way up to Apalachicola. Like the others said, Dunedin is a cool little town (with some great craft beer if you are into that--check out 7thSun. Honeymoon Island and Caladesi are beautiful white sand beaches--some of the best in the U.S.
 
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If you want to take a drive and see what Florida used to look like, head north to the Crystal River area and even all the way up to Apalachicola. Like the others said, Dunedin is a cool little town (with some great craft beer if you are into that--check out 7thSun. Honeymoon Island and Caladesi are beautiful white sand beaches--some of the best in the U.S.
Haven’t been to Crystal River in about 30-40 years huh? Nothin here looks like it used to!
 
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