In 2016, Michael McGregor was in his early 30s, living in Mexico City and hanging out with a group of local architects and musicians, when he began to paint.

Inspired by the city’s vibrancy, the budding artist — an expat from Brooklyn, where he’d spent a decade making a living as a writer and D.J. — began to depict birds, flowers and other everyday objects in colorful still lifes that helped him hone his artistic style.

At the same time, he started making sojourns to far-flung locales, using Mexico City as his base. “I had set an Airfarewatchdog tracker for flights to Tokyo for under 500 bucks round trip,” Mr. McGregor, 40, recalled last month during an interview at his studio in the Highland Park neighborhood of Los Angeles. “I went to Japan for a month. I went to Korea for a month. I was traveling all over Mexico, to L.A., to New York.”

In the midst of all this, Mr. McGregor’s sister stayed at a Ritz-Carlton (“Maybe somewhere in the Caribbean?” he said) and gave him some of the hotel’s stationery, printed with its lion’s head and crown logo. “I made a bunch of drawings and posted them on Instagram,” he said. “People were super into them.”

Those initial pastel sketches spawned a series of colored pencil drawings on stationery from some of the most celebrated hotels around the world, including Chateau Marmont in Los Angeles, Le Meurice in Paris, the Connaught in London and the Taj Mahal Palace in Mumbai. Drawn in hotel rooms, cafes, bars and airports, and aboard planes, buses and ferries, the playful scenes capture moments and objects from life on the road.