Levy visits some of the world's most beautiful and intriguing destinations in Costa Rica, Finland, Italy, Japan, Maldives, Portugal, South Africa and the United States, exploring remarkable hotels and the places and cultures surrounding them.

Levy ventures even further off the beaten path, inspired to experience local practices and global escapades with friends both new and old, including preparing for Midsummer in Swedish tradition with a moose-tracking adventure, visiting his mother's childhood homeland of Scotland for the first time, dining with a luminary and taking a bite out of French cuisine in Saint-Tropez, embracing wellness with a hay bath under German thatched roofs on the island of Sylt, voyaging on a Greek fishing expedition around Milos, learning medieval customs and harvesting grapes in Italy, and playing soccer with an iconic Spanish star in Seville, Spain.

After confronting his fears and stepping outside his comfort zone in the first two seasons, Levy is inching closer to becoming an avid traveler. But before he can claim that title, he's discovering what the “ultimate travel bucket list” is all about, and he gets a little help from a very special guest, the Prince of Wales. This season, Levy is also joined by a few famously familiar faces — including multiplatinum superstar and five-time Grammy Award winner Michael Bublé; Levy's daughter, “Schitt's Creek” and “SurrealEstate” star Sarah Levy; NOWZ, one of the newest K-pop boy bands; and Rahul Dravid, former Indian cricketer known as one of the greatest batsmen in the history of cricket.