PODCAST | How Sailing Totem Made “Someday” Happen

Behan and Jamie Gifford of Sailing Totem have been cruising full-time with their family since 2008, turning a dream into daily life at sea. Courtesy Behan Gifford

In the very first episode of Ahoy!, the Cruising World podcast, longtime voyagers Behan and Jamie Gifford of Sailing Totem share how they went from dreamers with a “someday” plan to full-time cruisers raising three kids afloat. Their story is one of patience, planning, and a shared love for the sailing life—and it offers inspiration for anyone wondering what it really takes to go all in.

The journey started well before Totem, their Stevens 47, carried them out of Puget Sound in 2008. It began with a shared sense of wanderlust, a love of the water, and a pivotal moment of clarity following the birth of their second child and the loss of a parent. “We realized we didn’t want to wait for some vague retirement window,” Behan says. “We needed to set a date.”

So they did. With three young children in tow—aged 4, 6, and 9 at the time—they stepped away from traditional careers, sold their house, and committed fully to a life afloat.

In this episode, host Andrew Parkinson talks with the Giffords about the realities of cruising as a family, the intentional lifestyle choices they made along the way, and the emotional and logistical preparations that made it possible. From the early influences that planted the seed to the decisions that shaped their route and rhythms aboard, the conversation offers both practical insight and heartfelt storytelling.

Now, nearly two decades and tens of thousands of sea miles later, the Giffords continue to inspire through SailingTotem.com, their mentorship work, and their honest reflections on what it means to live a life under sail.

Listen now on Spotify or wherever you get your podcasts.

Explore more from their journey at cruisingworld.com/sailing-totem and sailingtotem.com.

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