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3 minute read

Tour Director Profile: Osciri "Osh" Chageg | Italy & More

October 28, 2025

It's hard to pin down only one thing,” Osciri Chageg says when asked to name his favorite aspect of being a tour director. “The world is filled with beautiful places, both architectural and geographical. I love showing our guests beautiful places; what could be better than being the person who shows beauty to people?”

 

“Osh is the BEST tour director we have ever had.”
Ellen & James Black
Atlantic Highlands, NJ

 

Born and raised in Rome, Osh earned a degree in Management Studies from Royal Holloway University in London before spending some time traveling and living in various places. Eventually, though, his road led him back home to Rome, where he’s been leading tours for the last 17 years. “I love looking at the surprise in people’s eyes when they see a beautiful new place which they fall in love with,” says Osh.

In addition to leading all five Italy small group tours (Portrait of Italy, Northern Italy, Italy's Classic Cities, Southern Italy & Sicily, and Sicily in Depth), Osh also lends his expertise by leading departures on Paradores & Pousadas, Scotland: Highlands and Islands, and Insider's Japan. Talk about well-traveled!

When he isn’t leading tours, Osh is likely focused on his other passion: photography. “This year I have been the official photographer for ... the Pompeii Cast Project,” Osh explains, “an archaeological project where the bones and teeth inside the famous plaster casts of the victims of the 79 CE eruption are studied for the first time.”

From photographing ancient relics to guiding tours in all corners of the globe, Osh reminds us how lucky we are to work with such a diverse and talented array of tour directors. To join Osh or one of our other expert guides on tour, navigate to the tour links above!

Monday-Friday 9 a.m. to 7 p.m. ET

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