Kayak Tours by Wheel Fun Rentals, Tarpon Springs

When Brian McInerney reflects on the humble beginnings of Wheel Fun Rentals, he points to his childhood passion for bikes. "As far back as I can remember, I had a real love affair with bicycles," he recalls. During a trip to Italy in 1987, Brian's affinity for cycling blossomed into a full-fledged obsession when he spotted locals' transporter of choice, the surrey. Inspired, he began importing the Italian four-wheelers to a rental business in the U.S. that eventually expanded into Wheel Fun Rentals, now a nationwide web of shops that also loans out bikes, electric cars and mopeds, and man-powered watercraft. Atop bicycles and surreys built for solo riders or entire families, patrons embark on self-guided tours of major U.S. cities. Led by maps and lists of nearby sites of historical or cultural significance, riders zoom down bike paths and safe, lightly trafficked streets. Adventuresome athletes can also compete in activities such as surrey scavenger hunts and blindfold obstacle courses navigated via shouted instructions from a seeing teammate or exceptionally long rounds of trial and error.