Lucky Traveler is about Leo McGregor, a twenty-year-old surfer dude living in Kitty Hawk, North Carolina. He and his Irish pal Jimmy Flynn were surfing and made a bet to see who could catch the best wave that day. Leo won the bet, and the payoff was one Powerball Lottery ticket. Leo was the single winner of the $156 million pot. After a couple of months of getting badgered by the locals for money and handouts, Leo decided he needed to get out of town, so she hatched a plan to hitchhike across America to Santa Monica, California, via Route 66. Even though most of the Mother Road was long gone, he planned to veer off the main roads as much as possible to catch some of the famous roadside attractions. Leo left Kitty Hawk and his girlfriend behind and began hitchhiking barefoot with only the clothes on his back and a customized backpack full of items he might need along the way. On his journey, he met numerous interesting people and saw a lot of interesting sights. At each town and with each person who give him a ride, Leo experienced a unique adventure. Some of the things Leo experienced included getting kidnapped by a bungling thief at a 7-Eleven convenience store, accidentally burning down a Mexican restaurant, and being in a van that flipped over the guardrail into a ravine and the driver turned out to be a drug dealer. Leo documented his journey in a journal on his tablet. He hoped to someday write a book about his journey and give the profits to charity. He reached Santa Monica in thirty-nine days and had grown in so many ways. Once he reached the West Coast, Leo had a decision to make. Should he spend a few days at the beach then head back to Kitty Hawk, or continue his soul-searching? His story continues in the sequel.