This Ol’ Boat: Circumnavigators Behan and Jamie Gifford Offer Lessons for the Long Haul

This enterprising couple turned their sailing sabbatical into a business offering instructions and guidance to aspiring cruisers.
Behan and Jamie on their boat, Totem.
Behan and Jamie at work in Totem’s cockpit, coaching a cruiser online while anchored off Baja California Sur, Mexico. Courtesy Siobhán Gifford

When Behan and Jamie Gifford warn cruisers to be realistic about budgets, they know of what they speak.

In 2010 in Tahiti, not even halfway through a planned three- to five-year sailing sabbatical with their three children, they had $100 left in the bank. Their house in Bainbridge, Washington, was underwater financially.

“We figured that we could either pull the plug and go back, or we could figure out how to make a living out of this,” Jamie says.

They proceeded to Australia, got shore jobs for a year and a half, and reinvented their sabbatical into a lifestyle: living aboard while selling stories, instructions, guidance and a fair amount of handholding to a growing clientele who dream of cruising. After circumnavigating and accumulating an encyclopedic body of practical knowledge, they established a cruiser-counseling business that ­manages to be both inspirational and practical. In six years, under their brand Sailing Totem, they have coached more than 400 clients.

You may have read some of their 2,500 pieces, many of them written for Cruising World, or spent hours on their website and social media sites. Maybe you drooled a bit during one of their motivational talks. Their goal, they say, is to make dreams real and realistic. 

The couple met in 1991 while sailing on Long Island Sound, where Jamie had established a reputation as sail designer for racing boats in Old Mystic, Connecticut. Both recall being inspired by the book Dove, which Jamie gave Behan on an early date. After settling in the Pacific Northwest, having three ­children, losing Jamie’s mother, and getting caught up in suburban mayhem, they realized that they needed to shove off. At the time, their kids—Niall, Mairen and Siobhán (names from Behan’s Irish-Celtic roots)—were 9, 6 and 4.

In 2007, they paid $190,000 for a 1982 Stevens 47 that provided room for five, and enough stowage and heft to cruise anywhere. They chose Totem as a name to reflect the spirit of native traditions, to “look out for us, take us where we wanted to go, a vessel of our hopes and dreams,” Behan recalls. 

They then spent more than $60,000 refitting what they had been led to believe was a turnkey boat. That experience underpins their first, best lesson for wannabe cruisers: “The economics of cruising is one people get wrong often,” Jamie says. Simply put, the negotiated cost of the boat is just the beginning. “No boat is ever turnkey.”

The list of bills can seem endless: haulouts, a survey, delivery—and that’s before any upgrades that a survey might reveal. For the past 10 years, the Giffords have spent approximately $3,500 a month to live aboard. That does not include the $30,000 needed to replace their engine.

The Giffords ask clients to fill out a form outlining where they want to go, their budget and their timeline. Almost immediately, problems show through. 

“People often come to cruising with the idea that they need a bluewater boat: ‘I want to be able to sail around Cape Horn in a storm fighting pirates, so it’s got to be tough,’” Jamie says. “And the reality is that boats have a lot more capacity than people give them credit for. Most people want to cruise the Caribbean, the Bahamas, the US East Coast.”

Behan adds: “There is a lot of dogma around good, old boats as kind of the right, proper boat for bluewater cruising. These boats have problems that the newer sailor doesn’t even know how to ask the right questions about, and the owner ends up in a pickle where either the boat has issues that they can’t manage or they get into a money pit trying to fix issues and never get to go. We want people to go. Our whole mission is helping folks get out there safely, comfortably, happily.”

One irony is that social media videos can make ­cruising look like a Disney movie. But if you hire the Giffords (on a retainer of $300 for three months or $1,000 per year), you start to get the real dope. You can sample a half-hour of their advice for $50.

Sailboat in Isla Carmen
Totem, anchored off Isla Carmen, Loreto National Marine Park, Baja California Sur, Mexico. Courtesy The Porter Family aboard Saltair.

“[Cruisers] come into this because it looks awesome on YouTube, and there’s umbrella drinks on the beach and all of that,” Jamie says. “Yes, we have sundowners and fun, because we love this. But the downside is that it’s hard work. The downside is passages that are lumpier than you thought and a toilet’s backed up.” 

Their job, they feel, is not to kill the dream but to recalibrate it. And they are talking about more than mechanical stuff.

“I had a crying-out session with a client this week,” Behan says. “They thought they knew what they were getting into, and then they realized they’re in way over their heads. So, we’re brought in to help them salvage the dream.”

According to Behan, one family with coastal experience took off into the Pacific only to learn, too late, that they didn’t like it. Another couple dismasted in a Pacific gale 1,000 miles west of Baja with three kids on board, including a 5-month-old born prematurely. A freighter rescued the mother and kids, while the husband worked on bringing the boat back.

The Giffords have found that a successful cruise rests on a three-legged stool: being financially sound, physically healthy and, Behan says, “everybody on the boat has to want to be there.”

Jamie has no problem telling people he doesn’t think they’re ready, but often, he’ll advise tiptoeing into cruising. “Go and have fun for a while,” he says. “Don’t run off into the deep end of the pool. We want people to have fun and be safe, and not risk the family’s safety and comfort.”

With their own children now in college and working, Behan, 53, and Jamie, 57, hope to wend their way through the north Pacific to Japan, Taiwan, Micronesia and Southeast Asia. “We’ve visited only 39 islands in Indonesia, and there are 16,000,” she says.

You can access the Giffords’ blog and other resources at