Selling everything to sail around the world sounds romantic until you hear what it actually costs. It isn’t just the money. It’s your identity, your routines, and the comfort of having a backup for everything. In this episode, Rita and I talk with Alison Gieschen and her husband Dan, who traded a successful equestrian life on a New Jersey farm for full-time liveaboard sailing on their 43-foot sailboat, Equus. What they found is that long-term travel is less about perfect plans and more about commitment. If you’re chasing a travel lifestyle of any size, whether that’s a full circumnavigation, part-time cruising, or just traveling longer with fewer anchors and fewer “someday” excuses, their story is a pretty practical blueprint.
What I liked most is that they make the dream feel human by showing where it started. For Alison it was a childhood built around horses, then an unexpected vision of sailing, then learning wind, trim, and confidence on small boats. Dan’s background at the United States Merchant Marine Academy added some real competence to the operation (a good thing to have when your home floats). Alison’s path shows how fast curiosity turns into skill when you just keep showing up. They met in a sailboat race, which is funny on its own, but the lesson is a good one: shared adventure is a pretty effective filter for compatibility. If you’re building a travel partnership, pay attention to how the two of you solve problems together before you bet everything on one big departure.
The hardest part isn’t the postcard moments in Tahiti or the Society Islands near Bora Bora and Raiatea. It’s the fear. Their first attempt at an ocean crossing turned into a brutal Gulf Stream storm, with 18 to 20-foot seas, serious damage to the boat, and the kind of gut-level panic that leaves lasting PTSD. The details are the kind that would make anyone researching ocean crossings pay attention: gear fails, water gets inside, a dinghy can turn into a dangerous battering ram, and sometimes the good decision is to turn back. Just as important was the recovery. A mentor helped them reframe the experience so they didn’t quit, and that one conversation became the hinge point in an eight-year journey. I suspect a lot of us have had one of those conversations, though hopefully with lower stakes and fewer waves.
Life aboard also turned into a laboratory for minimalist living and creative work. With limited space and fewer distractions, Allison writes across genres, using travel, scuba diving, and cross-cultural experiences to shape children’s books, memoir, and adult fiction. They made a good case that having fewer possessions can be liberating. You stop working to feed your stuff and start building your days around meaning, movement, and people. (I looked around my own garage when they said that, and I’m not going to tell you what I found.) They stay close to their kids and grandkids through visits, FaceTime, and simple rituals like maps and pins, which proves that full-time travel doesn’t have to mean disappearing. And the closing tip from Rita and me is a simple one: book early for peak-season cities like Reykjavik and the big cruise gateways, because availability and prices can shift dramatically months in advance.
Click below to listen!
Leave a Reply