There are group swims daily at Clearwater Beach. As noted check the Swim Clearwater Facebook group. Also check OWS Leo Brecino on FB. He's tied closely to Swim Clearwater but has his own events. On Sat Aug 15, there will be the next iteration of the Rainbow River Swim at KP Hole Park in Dunnelon. This is #3 for this summer and WILL happen. Anticipate anywhere from 50 to over 100 swimmers. It's 3.6 miles down river - crystal clear and 72 degree water - but with the current you will end up taking about the same time as your 2.4 mile IM swim. Cost is $5 to KP Hole and $20 to Leo. They will shuttle you back to your car. Check his site for deets. This is a must do Florida swim for anyone. The 4th event of the series is Sun 6 Sep and will be a race.
Lots of groups riding out of San Antonio, FL on Sat/Sun mornings starting between 7-8am. I'm not sure if they are organized though.
See this link for other group rides:
https://www.chainwheeldrive.com/...ts-calendar-pg35.htm Also check "Aeropro Endurance & Event Prep Rides" on Facebook. They ride in San Antonio and in Town. They also hold criterium races in Woodland Industrial Park off Waters Ave just south of Carollwood.
Good luck.