There's quite a bit of variety here within an hour's drive, and I tend to choose based on the wind direction, or lack thereof. Pedaling and light sailing up and down the lower Hillsborough river, with lunch stops if you like. Upper Hillsborough river is great for wildlife and alligators, but mostly pedaling. Sailing around downtown Tampa, from waterfront mansions to tall buildings to cruise ships and industrial traffic. With a north or south wind, the East-West rivers are great, like Alafia and Manatee, where you can choose city and/or nature, and head into the bay too if you're in the mood. With an East wind I enjoy Clearwater and sailing along the gulf beaches down to St. Pete. A West wind means the ICW is a good bet.
Here's an easy site to check wind and weather forecasts (click on "back to maps" to pick a different location:
https://www.windfinder.com/forecast/clearwater_beachI enjoy a good breeze, but the TI likes flat water, so my choices above get me both.
Let me know if you head this way...
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