To kick off his trip across the pond, Shep landed at Heathrow Airport to the worst passport-check line he's ever seen in his travels there.
"Gonna take at 3.5 hours at least to get through," he wrote on his Instagram Stories as a caption to a selfie video panning around at hordes of people in line. "Amazingly understaffed."
Luckily, the painful wait gave way to a lot of fun once he was able to escape the airport.
Soon, he was having a "surreal" experience: drinking outside the House of Lords along the banks of the River Thames "with our friend who is an actual Lord."
The next day, he got ready to attend the Ascot horse races — check out his incredible before-and-after looks:
Once he got there, he was ready to go royal!
He joined some friends that included pals from Kentucky who owned some of the horses who were racing.
What's next, Shep — tea with the Queen?
Photos: Shep Rose/Instagram