Zach starts off his show in Los Angeles where he counts down the top five things he's always wanted to do, from trying out to be a contestant on "The Price is Right," to learning to dance like a pop star, to surfing the Southern California waves.

Zach is rollin' into Chicago where he'll take a spin on classic waterfront rides at Navy Pier, join in some summer festival fun at the Taste of Greece, and strap on his first pair of water skis ever on beautiful Lake Michigan.

On this trip to the Big Apple, Zach is in New York City where he'll take a tour of Manhattan 2000 feet above the ground, try his luck at speed dating and fulfill a lifelong dream of doing stand-up at world-famous Caroline's comedy club.

Zach is getting an insider's look at San Francisco, where he'll catch his very own crab on Fisherman's Wharf, feed his sweet tooth with a tour of the Jelly Belly factory, and fulfill his father's lifelong dream of sailing under the Golden Gate Bridge.

All bets are off when Zach hits Las Vegas! Zach tries his luck at gambling for the first time, samples a famous Vegas buffet, and catches a glimpse of some showgirls. Find out if what happens when Zach tries his luck as he takes flight Vegas style.

From biking to brewing, food carts to coffee tasting, Zach is exploring Portland, Oregon where the city motto is "Keep Portland Weird!" It is here that he will conquer his biggest challenge yet - rock climbing in Mount Hood National Forest.