Reef and huge waves in the Gulf....not gonna happen. It would be worth the drive from Sarasota to get to Ft. Desoto or Skyway as mentioned above for flat water. Seabreezes may be the call for the remainder of the week, so wait for them in the afternoon to ride Gulf side.
Check out
www.tampabaykiteboarding.com for great links to launch/riding areas and weather links for local wind info.
Have a great trip.
Steve-O
ps. I don't think the trolley's exist in Sarasota, only in Pinellas.