When Chaska native Nabil Amra stepped off his sailboat and onto a dock in Portland, Maine, in May 2017, he worried he’d made a mistake.

Amra had just completed a 2,000-mile solo cruise from Puerto Rico, enduring 23 days of freezing temperatures, storms and isolation during his longest sailing trip to date. The journey was Amra’s qualifier for the 2018 Golden Globe Race around the world, but it also made him doubt his decision to sign up for the competition.

Days later, Amra was ready to be back at sea. “You are a nation of one, and it’s beautiful feeling to be left to your own devices, sink or swim,” he said. “Who doesn’t like a challenge like that?”

This summer, he will undertake his biggest challenge yet when he and 29 other skippers embark on a nonstop, 30,000-mile race around the globe, each sailing alone and without the help of modern technology. The 43-year-old Palestinian-American hopes to raise awareness about the Israeli government’s restrictions on Palestinians’ travel.

Amra, who worked as a foreign exchange trader, was introduced to sailing by a co-worker about 13 years ago. He and his brother, 48-year-old Edina resident Ziad Amra, bought a boat together a few years later and began sailing regularly on Bde Maka Ska (Lake Calhoun).

The original Golden Globe Race in 1968 marked the first round-the-world yacht race. This year, restrictions on equipment — intended in part to honor the first winner Robin Knox-Johnston — mean competitors will sail in yachts designed before 1988 and rely on celestial navigation, old-fashioned weather-tracking and radio communication.

Each boat will have a satellite phone and GPS for emergencies, but competitors who use them will be disqualified, according to the race rules.

These retro rules level the playing field and make the race accessible for people who can’t afford pricey boats or technological equipment, Nabil Amra said.

However, these older boats are also much slower. A modern racing boat can circle the world in about 80 days. Amra is aiming for 270.

“These [boats] are fat sea donkeys,” he said. “Very seaworthy and safe, but they’re not speedy.”

He will be sailing a Biscay 36 Masthead Ketch, built in the early 1990s.

The boats will need to be strong to survive the Golden Globe’s treacherous route. Competitors will set sail from France on July 1 and travel around the southern edges of Africa, Australia and South America, where conditions are rough, gusty and cold, even during summer months.

Ziad Amra said their family is worried for Nabil Amra’s safety, but they’re enthusiastic about his efforts to raise awareness about some of the challenges Palestinians face.

Nabil Amra was born in the U.S. to Palestinian immigrants, and their family moved back to Palestine in the late 1980s, during Palestinian uprisings against Israel.

I have “a can-do attitude and some know-how and diligence that comes from what I learned by living here,” Nabil said. “And then you look at my other side. I got tenacity and endurance from oppression. … If I can put those together, I feel like I have as strong a chance as anyone.”

Rilyn Eischens is a University of Minnesota student on assignment for the Star Tribune.