Playtime Watersports

A white sail propels a 50-foot sailing catamaran out into Biscayne Bay. The wind-powered watercraft belongs to Playtime Watersports, whose captains narrate ocean sailing tours or host private and corporate events as sunsets paint the sky. Elsewhere on the bay, wave runners and pontoon boats—two of Playtime Watersports' other rental watercraft options—churn up water as they drag race with thrill-seeking dolphins.

Despite its name, Playtime Watersports doesn't limit itself to on-water revelry. The staff hosts corporate outings such as Beach Olympics, with events including beach volleyball, sand sculpting, and scavenger hunts.