Introducing: The 5-Year Plan to Liveaboard

By: Kit Case

We spent the past (almost) five years living aboard our Valiant 42 sailboat, StarGazer. In this post, and a series of articles to follow, I plan to share our stories and give you tips for how to make the liveaboard life work for you, as it did for us. I encourage you to experience the sense of freedom and peace that life aboard a boat can bring.

Our Backstory

Before my husband, Roy, and I were even a thing, we were sailing buddies. We met 15 years ago, both into sailboat racing (on other people’s boats). We both belonged to the same sailing club. We had similar dreams, including the dream of sailing full-time. What started out as friendly conversation led to pointed discussions and then to full-on planning. We spent the first few years clearing debt, consolidating homes, and seeing my daughter through college, getting married somewhere in the middle. All the while, we obsessed over Yachtworld and dreaming of a time when we could quit our jobs and Just. Go. Sailing. Just sailing. Really. Just sailing. Dreamy, right?

How do dreams come true? A willingness to try something crazy, combined with a lot of planning and then having the gumption to jump when it’s time to jump. Just do it, as Nike reminds us. Or, do the version that works for you.

Some people move aboard a boat as a forever decision, a complete lifestyle change. We, however, chose to give ourselves a 5-year window. Part of that decision was based on money - the financial planners thought that me working longer was wise for our long-term goals. Even as Roy was reaching retirement age, I was a few years out and essentially planned to play hookie for a while. Seemed like a fair exchange. The other reason, also based on money, was that we hoped to be able to sell the boat before too much depreciation had occurred. We knew that, like many people, we were not likely to keep the boat for the 20-year mortgage term. We never expected to make money on the deal, we just didn’t want to lose too much, either. Many calculations led us to The 5-Year Plan. The unexpected offer from my employer to work part-time, remotely, and make enough to pay for our health insurance, sealed the deal. 

Finding the Right Boat

Once we got our ducks in a row and convinced ourselves that this could work (with great support from our family and friends, I’ll add), we started looking at boats in earnest. Ray Neglay of Seacraft Yacht Sales turned into our biggest supporter. To him, the idea wasn’t crazy, not at all. Tons of folks sail off on boats. It’s just what you do. So, we got to it.

We looked at boats locally. We took a trip out to Annapolis in January, when the boats were 99% on the hard for the winter, all lined up and under wraps. We looked at a ton of boats. We began to narrow our focus. There were spreadsheets.

We made an offer on a Valiant in Annapolis that didn’t come to fruition. Then, I went to San Diego to look at one more Valiant, by myself, while Roy was away on work. She seemed like the one. I called Roy from a park bench in Balboa Park, t-shirt weather in February, to tell him all about her.

Without Roy seeing the boat first, to everyone’s surprise, we made an offer. We soon all met in San Diego for a test sail. We knew a Valiant would perform in heavy weather - they’re known as excellent global sailing vessels built with a combo of performance and sea-kindliness  - but, we were sold when, in only 6 knots of wind on San Diego Bay, she picked up and moved. Roy and I looked at eachother and thought “Yep.”

Sunset over Mission Bay, our first destination that involved leaving San Diego Bay.

Sunset over Mission Bay, our first destination that involved leaving San Diego Bay.

The 5-Year Plan Begins

Loose ends were wrapped up. Parties were held. We sold or gave away almost all of our possessions. We packed what was left into our Honda Element, aka “the measuring cup.” Roy said, rightly, that if it didn’t fit in the car it wouldn’t fit on the boat - and we drove down the coast at a sightseer’s pace. After all our years of dreaming and planning and looking, the time from finding our boat to moving to California was remarkably short. We moved aboard about seven weeks after finding the right boat. 

Eucalyptus trees on Catalina Island.

Eucalyptus trees on Catalina Island.

We found StarGazer sitting at the dock, in her 3rd year up for sale. She was due for some loving. We spent several months fixing her up, getting repairs and maintenance done and adding a few upgrades to bring her up to what we wanted in a liveaboard. We enjoyed a few months of sailing the coast of southern California, with an amazing chunk of time at Catalina Island. That first September, we had to face the decision of whether to turn left and head to Mexico and beyond or to bring StarGazer back with us to the Pacific Northwest. We weren’t inclined to head to Hawaii. Staying in San Diego, although we loved living there, was not an option we relished. Every destination seemed so far away from San Diego, and we were not sure we were ready yet.

People we spoke with in San Diego didn’t believe us when we described what sailing is like up here in the Pacific Northwest. Washington’s endless anchorages and hundreds of marine parks with mooring balls, spread out over a hundred+ miles of protected waters, followed by hundreds more miles of near-coastal sailing up through the Salish Sea and on into the Discovery Islands and beyond seemed unbelievable, to them. They all assumed we were exaggerating. It is unbelievable here. It is some of the best sailing in the world, in my humble opinion. So, we brought StarGazer home. We had four more years in The 5-Year Plan.

The Rest of the Story

In future posts, I will expand on the steps we took to comfortably live aboard a sailboat full-time, while working part-time and exploring the Salish Sea - on our schedule, at our pace - for the past four+ years. As I go along with my storytelling, I hope you’ll reach out to ask me questions and share your plans and dreams. Let’s start a discussion. I would love to talk with you as your plans take shape. Shoot me a note at: kit@seacraft.com.