I’m Josh, and my wife is Haley. We are digital nomads who work and live on our 1986 Nauticat 33. We aren’t the typical digital nomads, though—we didn’t sell everything and quit our jobs to ride off into the sunset. Keeping our corporate jobs as a Senior Recruiter and Graphic Designer, and renting our house in Idaho, has allowed us to travel now while continuing to plan for the future. You can follow us along this journey on Instagram: @Cruisincasa.

Let’s start nearly four years ago, in 2021, when Haley and I took my grandparents’ Eurovan on a two-week trip through Utah and Colorado. We quickly realized that we could live in a van, travel, and work from anywhere we wanted. COVID was the catalyst we needed—our jobs went remote, and we saw the true possibilities of a nomadic lifestyle.

The day after we returned from our two-week trip, we purchased a 1993 Toyota Dolphin that was in dire need of a refit. For the next two years, Haley and I spent every evening and weekend rebuilding the RV from the ground up. Looking back, the skills and knowledge we gained during that time were priceless—we learned to build every system: structural, plumbing, off-grid electrical, and mechanical. The saying that kept us going (these were not easy times) was: “Use the evenings and weekends to build the life you want, not escape the life you have.”

Fast forward two years—the RV was finally ready, and we set off to travel through the U.S. with the goal of visiting all 50 states. We left Boise, Idaho, in September 2023, heading to Astoria, Oregon, and followed the coastline down to San Diego, eventually making our way to Key West. As we traveled from town to town along the coast, our love for the ocean grew. I vividly remember sitting on the white sand of Siesta Key, watching boats head south to the Keys, and realizing we needed to start thinking about sailing—and what steps we’d need to take to make that dream a reality.

I grew up sailing on the west coast in Southern California, learning on Sabots and Lasers in Dana Point Harbor, with yearly trips to Catalina on my grandparents’ 30-foot sailboat. Haley, on the other hand, grew up in a small town in Eastern Oregon—her only boating experiences were yearly trips to the coast or summers on the lake. Knowing this, I realized we needed sailing lessons to learn how to sail together.

Living in the RV allowed us to “shop around” for sailing lessons that fit our budget but, more importantly, offered quality instruction. We found Sara Bay Sailing, which checked both boxes and even let us stay the weekend in their parking lot on Longboat Key. The ASA 101 course was invaluable—Haley learned the ins and outs of sailing while we figured out how to work together on a small boat. A huge shoutout to Charlie at Sara Bay Sailing—he’s the real MVP—giving us the knowledge we needed while allowing us to learn through our own mistakes. With ASA 101 completed, we pushed on toward Key West, knowing we still needed to take ASA 103 and 104 somewhere along Florida’s coast. Again, thanks to the RV, we could be selective, and we found the perfect spot in St. Augustine at St. Augustine Sailing. Nuri, our instructor for both courses, was incredible, and we even got to sail on a nearly brand-new Jeanneau 35. With these basic certifications under our belt and my prior sailing experience, we felt confident that life on the water was for us. (Foreshadowing: we don’t always plan well.)

So, if you want to buy a boat—where do you start? The simple answer: the internet. (Listing sites such as YachtR.com and RightBoat and Sailboatlistings are great resources). We scrolled endlessly through listings of sailboats, unsure whether we wanted a big 40-foot+ boat or something smaller in the 30-35 foot range. Eventually, we decided that jumping straight into a massive boat was both risky and impractical, so we focused on the 35-foot range. That’s when we found a beautifully maintained 2000 Dufour 38 Classic—it felt like the boat of our dreams.

We purchased the boat in March, moved aboard in April, and started heading north to stay out of the hurricane zone by June. But as we traveled, we quickly realized the boat wasn’t going to work for us—or for our two pets, Scout and Stella. By the time we reached Brunswick, Georgia, we decided to list the boat for sale, move back into the RV, and drive all the way back to Idaho for the summer. That’s where Carolyn comes in—she helped us sell our first sailboat.

To our surprise, the Dufour sold within a month—after sitting on the market for nearly a year before we bought it. Did we lose money? Oh, absolutely—but when something doesn’t work out, sometimes you just cut your losses and move on.

While back in the Pacific Northwest for the summer, still living in the RV, we took a trip to Anacortes and the San Juan Islands to figure out what kind of boat we really needed to accomplish our goals. We don’t want to cross oceans, but we do want to complete America’s Great Loop, explore the Bahamas, and sail the Caribbean island chain. With that in mind, we considered trawlers—but anything in our price range wouldn’t handle the islands well. We still loved the idea of a sailboat, but we needed one that our dog could navigate easily—meaning no lifting her up and down the companionway. That’s when a pilothouse became the obvious solution, offering only a couple of steps between the cockpit and saloon.

I stumbled across Nauticat motorsailers—they’re the perfect hybrid between a trawler and a sailboat. They’re ideal for the Great Loop while offering the seaworthiness to expand our cruising grounds to the Caribbean. And here’s the crazy part—Carolyn, the same person who helped us sell the Dufour, happened to have a Nauticat 33 for sale in Florida. I didn’t even realize it was her listing when I reached out, but it felt meant to be.

And that brings us to the present—currently one week into America’s Great Loop. We left Stuart on February 14th and are now in New Smyrna Beach. It’s amazing to reflect on how far we’ve come and the dumb decisions we’ve overcome along the way. Expecting to “cross our wake” in 15 to 18 months is surreal—but with the experience we’ll gain over this 6,500-nautical-mile journey, the islands and beyond will feel within reach.

You can follow us along this journey on Instagram: @Cruisincasa.