We yearn for a more simple life. The idea is that we spend time in a coastal area and leave when we decide we’ve spent enough time, or when the weather dictates it. We explore the lands, meet the people, taste the food, and play in the water, taking photos and videos, and writing about it along the way. Simple. But in order to get to that point, we have to jump through many complicated hoops.

I can categorize each hoop as fitting within one of 5 phases to our cruising adventure. At a high level they are defined as 1) before we owned the boat (done), 2) before we lived aboard (done), 3) before we cut our ties to land (working on it), 4) before James retires (while cruising part-time), and 5) after we are both retired and cruising full-time. The end goal is not a destination but a lifestyle, during which we are not connected to any one location for too long. Cruising on a sailboat is a nomadic approach to living with learning, connection, and adventure at its core.

Each of the journey’s phases involves preparation to get to the next phase, and this preparation has proven to be quite complicated at times. We are currently cutting ties to land life and some of what we are going through and planning has exhibited such complication that we’ve had to enlist the help of legal and cruising professionals, as well as the help of friends.

Before We Owned the Boat

Deanna at the helm docking in Long Beach

James helping with the foresail on Britican, in Grenada

We put a huge amount of effort into determining what type and size of boat we wanted to cruise and live in. James’ first investigation into this resulted in a conclusion that we could purchase an appropriate boat for $30k. It would be fair to conclude now that he wouldn’t be happy with anything less than a boat worth an order of magnitude above that! We needed to engage a broker and a marine lawyer to support our questions and legal arrangements for 3 offers, and we ended up creating a company (LLC) that complicates all marina checkins since the boat isn’t owned by us as individuals but as managers of the LLC. We engaged a surveyor, another set of eyes since we couldn’t travel during the pandemic, and an amazingly knowledgeable and friendly pair of highly experienced cruisers at Sailing Totem to provide answers for all the questions that we had, and those we didn’t even know we had.

More details on the specifics of the boat purchase can be found at our posting We Bought a Sailboat!

We also took sailing classes and got our certifications, attended Cruiser’s University at the US Sailboat Show, named and renamed the boat and dinghy, designed the logo, and spent a week with a cruising family aboard Britican to verify that the cruising life was for us. On the logistical side of things, we talked (and talked and eventually ended up parting) with an accountant about the concept of making a business out of the boat to earn a small amount of income during our travels and potentially write off the boat (conclusion: nope), and secured insurance that would cover us in the areas where we are cruising. It’s not such a common lifestyle that every service provider has a good understanding of it, and we find ourselves explaining and teaching them almost as much as they inform us.

Before We Lived Aboard

Erin Skye on the hard in La Paz

Once we’d purchased the boat, we had to get her transported from Florida to Mexico, deciding between various permutations of our personal involvement, the involvement of a professional captain, and using a cargo ship for carriage. After careful consideration between the options, we chose to have a captain move her to the harbor where she could meet up with the cargo carrier Pietersgracht that would take her through the Panama Canal to La Paz. We would have loved being on that transit, but COVID prevented us from partaking in the adventure beyond taking screen captures of the canal web cams.

In La Paz we had a project manager representing us to the Mexican customs officers with US Coast Guard registration documentation, engine serial numbers, and various other information, some that we had to get notarized while the officials waited.

We took advantage of the skilled labor there and addressed various maintenance items required by the insurance company and for safety and comfort. Erin Skye was taken out of the water (put on the hard) when hurricane Genevieve threatened the southern tip of Baja California, which actually resulted in only a few stronger winds. Finally when we were more comfortable with the COVID situation, James flew to La Paz to bring Erin Skye up to Ensenada with a captain who could sign him off to be the skipper for insurance purposes going forward.

While Erin Skye was getting all that attention, we were moving from our house to an apartment, and shedding most of our material possessions.

Before We Cut Ties to Land

This is the phase we are in now, after we moved aboard and as we prepare to leave Emeryville Marina where we’ve lived for 9 months. We expect to start our next phase within a couple of months and there are so many balls that we are juggling. The most slippery are the boat projects, setting up domicile, arranging for schooling and Boy Scouts, and sailing and travel preparation.

Admiring the new cabinetry

Boat Projects

As I write, James is creating a template for new holes in the helm fiberglass to accommodate the electric winch that allows us to reef (reduce the amount of sail that is out) without leaving the helm, and therefore reducing weather-related risks. We are currently in the middle of 9 other projects: hatch replacement, solar arch installation, solar panel installation, battery replacement, electrical upgrade and outlet installation, galley cabinet replacement, galley oven & stovetop replacement, cabin cabinet building and installation, and mainsail reefing repair. We don’t need to complete them all before we set sail down the California coast, but we’d really like them done soon.

Recently we returned from putting Erin Skye on the hard again (this time in Napa Valley) to address some maintenance issues like repainting the bottom and replacing through-hull seals, as well as an upgrade or two like installing our transducer to capture sonar reflections below the boat.


Researching options and specifics about how to change our official “domicile”, which represents our permanent home base versus “residence” which is the temporary home where we are physically located, has proven to be the most difficult and frustrating of all our preparation. I’ve received conflicting information from various sources, including lawyers and mail services in 3 states, and current cruisers responding to my queries on social media.

The most important factor in creating domicile is the intent to return to our state of domicile when we are finished with our cruising. We’ve known for a long time that our target retirement state is Florida, but the various counties appear to handle the domicile question differently. We will be moving to the chosen county before the end of the year, where we will get our driver’s licenses, meet with lawyers, set up accounts, and become established in the community. Plus, Ethan will be able to get his driving learner’s permit while we are out there!

Schooling and Boy Scouts

Ethan enjoys being the dinghy skipper

The location where we domicile dictates the homeschooling laws and regulations we need to follow regarding Ethan’s education, at least for a while. We’ve investigated several options, learning about umbrella schools, reporting requirements, curriculum and graduation requirements, as well as the driver’s education process. Ethan notes that he doesn’t want to be a “Florida man”, but I helped him understand that behavior is what provides that notoriety versus simply where one’s domiciled.

We will need to convert from part of a Boy Scout troop to the Boy Scout Lone Scout program, since we won’t be located near any troop for very long. This requires us to stop using their online advancement system and report merit badge and other accomplishments to a remote council manually, through email. When I learned of this, I couldn’t help but mention to the Boy Scouts administrator that the remote online system should align well with the remote class of boy scout. Patience is something I’ll need to embrace more with the new lifestyle, I’m thinking.

Sailing and Travel Prep

Even now I’m making plans for the next phase, between June and December of this year. I’ve been researching the ports along the way down the California coast, and looking into how and where to visit the Channel Islands. I’ve identified many ports to check out if the timing and weather are right, and we’ll be making decisions along the way regarding which to skip, if any. Plus, we have family and friends to visit along the coastlines if the timing can work out.

One might think that with a career in project management, I’d be whipping out some scheduling tools to apply to all these tasks and projects, and one wouldn’t be wrong in that thinking – it’s in my blood. I recognize that it’s essential to balance the rigor and ceremony of project management so that tentative plans can be made, with the required flexibility and fluid lifestyle of cruising on a sailboat. So, in my planning documents I have included data with titles like “tentative departure date” and “approximate cruising time.” Perfectly nimble.

Walking along our home dock

We have a risk log with over 100 entries, one or two of which we select to review daily to identify how to prepare for and mitigate risk to an acceptable level. For instance, we recently reviewed the risk of getting a fishhook in the eye (a risk identified and kindly brought to our attention by the Emeryville Yacht Club Commodore, Britta), and though Ethan and I were cringing and begging James to stop sharing details of a similar account, we are now well-versed in how NOT to react and what to do if this risk is realized. More importantly, we have all agreed to wear glasses whenever there is fishing gear out!

As for our car, I’ve been working out the timing and coordination of when to buy it out of the lease, when to take it to San Diego, how to store it while we’re cruising down the coast before we end up in San Diego, and when and where to sell it. I’ve already looked into Mexican insurance so we can drive between Ensenada and San Diego if we decide to do that. Erin Skye is set with documentation from the US Coast Guard for the next 5 years and annually we’ll register our dinghy (dubbed “Sunset” by Ethan). Last month we all received our updated passports and soon we’ll apply for a Mexican temporary residency permit.

Before James Retires

For a few months we will be cruising while James is still employed full time, so Ethan and I will enjoy each port during the days and James will join us in the evenings and on weekends. We’ll only sail and move between anchorages and/or marinas during the weekends or when James takes a vacation day, but we have months to make it down the California coast so a slow pace sounds perfect. My focus will be threefold: 1) passage planning and weather routing, 2) boat-schooling, or preparing for boat-schooling, and 3) destination activity planning. This last one is what I’ve always loved about vacations, determining what we’d do after arriving and making sure that we are informed and prepared to make the most of those activities. Integrating schooling with our location will be so interesting and make it more engaging as well.

We will need to solve the medical care issue before losing our insurance, determine if anything besides catastrophic insurance is needed while we are out of the country, and if not, how to be covered when we travel back to visit in the US.

A view we hope to have from a Mexican beach, near the end of this year

After We Both Retire

Our preparation doesn’t extend this far, with the exception of knowing that we will cruise down to Ensenada, then down the Mexican coast to at least Puerto Vallarta and decide where to go from there. As James puts it, “we’ll decide whether to turn left or right.”

In our travels we may find a location that we deem perfect for retirement outside the US or we may just end up cruising back to the US, into the Gulf of Mexico and finding a nice simple place to reside, on land near the water. I expect we will be able to appreciate our cruising experience and use the flexibility and other skills we hone along the way to ease into a truly simplified land-based lifestyle when this adventure is over. And I expect that the transition will be much less complex than the one we’re going through now. It will take a while to determine if that’s the case, but I’ll let you know!



Top/featured image is by Tyler Lastovich on Unsplash

Final image is by Arusfly 🌿 on Unsplash



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Written by Deanna