State of the Union / When Osher Met Ashley

An Israeli skipper and an American Olympic sailor fall in love on a tropical island.

Danna Harman
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Danna Harman

Once Upon a Time

For all those who thought sailing around the world and finding your true love anchored right next to you in Fiji is the kind of thing that only happens in fairytales: Welcome to world of Osher and Ashley.

The story begins in a far away land. Or rather, in two lands far away from each other.

In 31-year-old Osher Perry’s case, it starts in Elei Sinai, what was once small Israeli settlement in the north of the Gaza strip. His Tunisian dad was in the police, his Yemenite mom headed a prison service’s drug rehab center. Osher spent every day– bar Yom Kippur – with his two younger brothers at the beach. He loved that land, he says. It’s where he grew up.

For 28-year-old Ashley Holtum, the story begins in Glenwood, Colorado where her dad, a ski bum and contractor, met her mom, a high school English teacher. It’s where Ashley and her older brother grew up. When Ashley’s parents divorced her dad moved to Washington State and her mom remarried and set off for New Zealand. Ashley headed to the University of Denver, where she studied criminology and Italian, got decent grades and played soccer. Then, junior year, visiting her mom and stepdad in New Zealand, a random cocktail-party chat led Ashley off in an entirely unexpected direction.

“I was talking to this woman, Sharon Ferris, who, turns out was a two-time New Zealand Olympic sailor, and who had, long story, come to the party, which was a housewarming for my parents, by mistake,” says Ashley.

Being polite and curious, Ashley asked a lot of questions, including at some point, half jokingly, “Will you teach me how to sail?”

To which Ferris responded, “How about next Sunday?”

Ashley, who had never sailed before, ended up being a natural, with terrific balance. And before anyone could quite understand how it all happened, she was taking a leave from college, training and competing around the world with Team Inspiration, a three-woman New Zealand yachting team whose members all eventually netted places on the national Olympic Yachting team. 

“Yeah, it was unexpected,” says Ashley, in what might be classified as an understatement. “We did really well.”

Journeying toward each other

It was the summer of 2005, and back in Israel, Elei Sinai was being demolished as part of the Gaza disengagement. Osher and his family, evicted together with the other members of the community, set up tents and caravans just beyond the disengagement line.

What was meant to be a short-term protest solution, turned into a yearlong saga: The government failed to find a place for the settlers to move as a community and the settlers, in turn, refused to budge.

“What happened there was nothing less than a crime,” says Osher, who had already left home to serve in the navy, but came back whenever he could and represented the younger generation on the settlement board that was negotiating with the Israeli government.

The crowded communal living, rain, mud, insecurity and anger all took their toll. Many families left. Osher’s parents divorced. He too was disillusioned. Two years later, needing a break – from the country and the navy, where he had by now served seven years and was a lieutenant commander – Osher took a year’s leave of absence and set out to circumvent the world by ship.

“I had always known what I was doing,” he says. “But then, for the first time in my life, I decided I had to let go – to trust that would lead to good, and new, places.”

On the Caribbean island of Saint Martin he joined an American yacht as a skipper and sailed off, around the British Virgin Islands, towards Panama, Ecuador, the Galapagos and across the Pacific. In Bora Bora, he met an Australian family and looking for a new gig, joined their yacht and headed to Fiji.

Ashley meanwhile, was winding down her professional sailing career.

“I decided to leave. I was 22 and I wanted to go back to Denver and finish my degree,” she says, admitting the intense and competitive lifestyle was a little lonely. Before heading back, she joined her mom and step dad for a two-month sailing trip.

“And that,” she says, “is when I met this good looking guy in Fiji.”

First sighting

“It was a Friday, and I was having a beer, hanging out with a group of about eight other ‘yachties’ on the dock,” recalls Osher. “We were standing in a semicircle and she was on the opposite end. Someone said ‘Hey, did you know she is Jewish too?’”

In fact, Ashley’s mom is Jewish and her dad is not. As a child, her family went to the Chabad House in Aspen once or twice, she recalls. They lit candles on some Friday nights and knew how to make challah, but that was about it. Osher, on the other hand, grew up Modern Orthodox but took off his kippa at 15.

In any case, no, he had not known. But what he did know, he says, was that she was the prettiest girl he had ever seen. He walked over to say hello. Ashley gave him some fresh challah she had baked.

That night, at a party on the beach, they danced together. Later, he invited her back to his ship, where he read her parts of his travel journals. He told her about how he had swum with a humpback whale and her calf.

“We were just floating together for three hours,” he says.

“I could tell that he was something special,” she says.

They spent two days together – and then sailed off in different directions.

“I wanted to cyberstalk him but I didn’t actually know his name. I thought it was Ocean,” says Ashley, who by then had returned to Denver to finish college. “I wrote a note to someone on Facebook who replied, ‘I think you are looking for someone else.’


Osher had set sail for Vanuatu and Australia, and then across the Great Barrier Reef, but he too was thinking about Ashley. “I definitely wanted to see her again,” he says.

Several months later, when an old navy friend suggested he take a break from the seas and join on a six month road trip across New Zealand and Australia, Osher tracked down Ashley’s parents, and made plans to stop by their house before he set out. As it happened, Ashley was home in New Zealand for a visit.

Then, since every good fairytale needs a wicked stepmother, wild beast or, say, psychometric flop to move the action forward, Osher’s friend got word that he had done terribly on his pre-college exams and cut out to go home and retake them. And the rest, as they say, is history. Ashley embarked on a six-month road trip with a guy she had very recently learned was not named Ocean.

“I told everyone I know, ‘If I come back in two weeks, don’t say anything,” says Ashley.

“I was freaking out.”

“We were going to be off-roading through the desert for tens of thousands of miles together. And we did not really know each other,” says Osher. 

Because of a problem with their Land Cruiser’s muffler, the drive was so loud they could barely hear each other talking. It was the best trip ever, they agree.

“I was more than smitten,” she says. “It was love.”

They hiked and went diving, slept in the car or tent and ate a lot of shakshuka. “Shakshukas with the red sand of central Australia,” he says.

He taught her the alefbet. She did a lot of the driving. They don’t remember ever fighting. 

Coming home

After the six months, they parted ways again.

“I needed to continue my own trip,” says Osher, who joined another ship in Japan and sailed to Korea, Singapore, across the Indian ocean and all the way back to Eilat. “I had been out of Israel for two years. And when I got home, I was done traveling.”

This time, they emailed, they called, they made plans and soon, with Osher home, Ashley was making her maiden voyage to Israel. “I said, ‘Come and see for a few months.’ I tried to reduce the pressure,” says Osher.

They lived in Ashkelon, near his mother. “It’s like being in tribe. Each of his parents has like ten siblings, and everyone has four to five kids,” she says. “You can imagine how hard it is to remember all their names, in Hebrew.”

Osher started a business degree and, as part of a course on social responsibility, got involved in Palestinian economic development and other co-existence projects. After graduating, he began working at the Portland Trust, a British non-profit foundation that promotes economic development as a way of engendering peace and stability between Palestinians and Israelis.

Meanwhile, Ashley, after rising up the ranks in ulpan Hebrew-language classes, is doing some private tutoring, and plans to start a degree in psychology. “It’s not like going for the gold in the Olympics,” she admits. “But, it’s good anyway.

Happily Ever After

Last October, the couple went back to New Zealand to visit Ashley’s family. It was Osher’s birthday, and they went for a picnic in Flagstaff to celebrate. They had never much talked about marriage before.

“We know the facts. Both of our own parents are divorced,” says Ashley.

“We never felt any pressure,” says Osher.

“Except when your dad told me my womb was drying up,” notes Ashley with a grin.

But there, at the picnic, overlooking the water, Osher gave her a little box. Inside was a gold ring he had designed.

“Oh my God, really?” Ashley said.

Her mother, whom they went to meet afterwards, cried.

The two are getting married in May. Meanwhile, they have made their first big joint purchase: a small yacht called “Moose.”

And then they lived, as it always goes, happily ever after.

For two people comfortable on the water, oceans weren't going to get in the way of a good thing.Credit: Moti Milrod
'We were just floating together for three hours,' Osher says of the couple's first date.Credit: Moti Milrod