Sailing adventure to 7 continents

Harry Anderson of Bainbridge Island will be the first to admit he did it backwards flying and sailing solo to the seven continents.

Not literally of course. He didn’t go backwards. But he did fly first, and he said he should have sailed first because it’s much harder physically, and he’s almost 73 years old.

He can’t be positive, but he thinks he might be “the only person to have done both.”

Anderson recently returned to BI for six weeks as his 42-foot sailboat Phywave was being worked on after traveling to Antarctica, the fourth continent on this trip. He hadn’t even planned for this until COVID hit in 2020. “I had to come up with a new idea to sink my teeth into,” he said by phone from Puerto Williams in Tierra del Fuego in South America.

Anderson set off in June from Annapolis, MD, after it took about a year to have his custom boat built. He sailed to Portugal in Europe then to Tangiers in Africa before heading to Brazil and then Antarctica. He called his last trip the “Mount Everest” of his journey. “I’m glad to have that one behind me.”

He has traveled all over the world, but “the voyage back north across the Drake Passage was brutal,” he wrote on his blog. The worst moment was when the furling line on the headsail snapped in 30-plus knot winds, “causing the entire sail to roll out and send the boat ripping along at high speed, essentially out of control.”

Eventually, he was “able to climb out on the violently bouncing bow, frigid seawater splashing over me, and attach a new line to the furler and get the sail rolled back in. I think I earned my sailing stripes with that one.”

Along with hairy situations like that, there is a lot more paperwork involved with sailing. It takes a lot more time so he doesn’t get to do as many tourist outings as he did when he flew his plane on a similar journey. When he starts back up, he plans to head to the South Pacific to Australia, then to an undetermined site in Asia before heading back to North America to conclude his trek in 2024.

Anderson said he doesn’t plan to take on another trip like this one. “The physical aspects are tougher for me. This is the last big, demanding adventure that I’ll do. After this one I’ll dial it back,” he said, adding he should have reversed the order and done the plane trip first.

Early years

Anderson was born in Wisconsin and later moved to the West Coast, where he went to the University of California at Santa Barbara. He went to the Midwest and then to Oregon, where he started a software wireless network company, which he sold in 2002.

He said he wasn’t really an adventurer as a youth, but he did like backpacking and mountaineering. He got into sailing as a teen with his dad in Southern California. After Oregon, he bought a 37-foot sailboat when he moved to BI, and he used it to sail Puget Sound, the San Juans and the Inside Passage for 12 years until he sold it in 2019.

He definitely is a world traveler, having been to 100 countries over four decades. He was just the fifth person to fly a single-engine prop plane solo to all seven continents in 2014. He has also hitchhiked across Africa, worked on four continents and published books on flights and software. He’s climbed Mount Whitney and Mount Kilimanjaro and traveled all over Europe. He learned to fly a plane in 1998 and has flown all over the country.

Plane adventures

Anderson, who is unmarried and has no children, moved to Bainbridge in 2002. His plane has a 310-horsepower engine and four seats, but for longer flights, he removes the backseat and replaces it with an additional fuel tank. He first flew around the world going east in 2011, and in 2019 flew back around the world going west. He used autopilot much of the time, but he still had to do the takeoffs and landings.

Anderson told the Review in 2019 that the best part of the flight was being able to see the world from a great perspective. “Obviously, it’s just a different view, from 10,000 feet up,” he said. “Flying commercially is OK, but it’s too high to see the farmer working in his fields or the beauty of the land.”

He’s had some “unnerving” moments in the plane, too. In his first round-the-world trip he faced headwinds going from Hawaii to California. He was afraid he might run out of fuel and thought about turning back. But suddenly the winds died down, and he was able to make it. “It was right on the edge,” he said. “If the winds had been ten knots stronger…”

Book writing

Anderson wrote a book in 2015 about flying to the seven continents. He’s planning to write one on his sailing excursion, too. “There are more compelling stories,” he said. What takes hours in a plane takes weeks on a boat, he said. “You’re out there much longer. You’re much more exposed to the weather.”

In the air, he can fly around bad weather or land and wait it out. But in a boat, “Once you’re out there, you’re out there. You can’t outrun it.” Anderson said he’s a little more trusting of the electronics on his boat. Even with autopilot, he wasn’t about to sleep in the plane, but he does on the sailboat. He said radar alerts him to nearby ships.

Anderson said he’s made lifelong friends in his travels. But while sailing he mainly gets to know the people in the marinas. He just doesn’t have the time to take off like he did when he was flying. In his travels, he does have some favorite spots. He’d like to go back to the Canary Islands, and he really likes Australia and Alaska. But if he does go back he will “let somebody else do the work.”

In all of his travels, he has felt safe most of the time. He felt welcome in Russia, but would be very cautious about going to Muslim countries like Iran and Afghanistan. Going to international airports has never been a problem, but a few times at domestic airports like in Argentina he ran into communication issues. He asked for permission to take off, and on the radio he heard, “This is a Spanish-speaking airport.” Anderson said he was able to “cobble together enough Spanish from high school to get airborne.”

He said he also had some issues in China, “because there are no small planes like mine” there. “They were at a loss,” he said. “They kept giving me instructions that I wasn’t able to do.” But “people are friendly and welcoming universally — that’s been true,” he said.

Note: Check out the blog and maps in the sailing section of his website at

Two penguins ride a block of ice in Antarctica.
Two penguins ride a block of ice in Antarctica.

Two penguins ride a block of ice in Antarctica. Two penguins ride a block of ice in Antarctica.

The sailing route Harry Anderson has taken so far.

The sailing route Harry Anderson has taken so far.



The sailboat Harry Anderson is using on this seven continent adventure.

The sailboat Harry Anderson is using on this seven continent adventure.

Harry Anderson and the plane he used twice to fly around the world solo.

Harry Anderson and the plane he used twice to fly around the world solo.