“Start where you are, use what you have, do what you can.” – Arthur Ashe

A sailboat is not the most comfortable of abodes, but the size constraints and comforts we forego compared to living in a house are a small price to pay for the adventure and freedom of the cruising lifestyle. Life is all about balance.

In less than a month our family will be going out the San Francisco Gate on our catamaran Erin Skye, to start our cruising adventure down the California coast, then into Mexico. From there we aren’t sure where we’ll go, but we know that we will explore parts of the world we’ve never seen before. As we prepare to depart from our land home base and reflect on the past few months of preparation leading to this point, I’m most grateful for the fact that we started the journey at all and accepted it as a goal versus an unattainable dream.

Living at the Dock of the Bay

Erin Skye at the dock

We chose to move onto our boat about two years before starting to cruise full-time, in order to learn about the boat’s systems, practice sailing, and reduce our cost of living before leaving our income behind. For the most part that was what we accomplished, but in retrospect we allocated too much time to this phase of the journey. After 6 months we ended up looking for a way to change our departure date to a year earlier.

With all that time, it was too easy to take my eyes off the goal of preparing, and sink into the routine of living at a marina. I volunteered to be room parent for Ethan’s school, Vice-Commodore for the yacht club, and Boy Scout troop reservation lead.

We also fell down the rabbit hole of projects, leading to a dearth of free time for James (aka MacGyver) and stress on my part due to living in a construction zone along with a compulsive need for everything to be in its place.

Cockpit table mid-project

What we didn’t think of was how the lack of usable space (though temporary) would impact the quality of life of the crew. Six months of living this way led me to decide that we needed to get to the more rewarding part of the adventure quicker, minimize the project work, and move off the boat when we undertake large projects in the future.

Trial Run

The decision to move aboard and live in a marina before jumping into the cruising lifestyle allowed us to make mistakes in a setting that was less risky, from a safety and financial perspective. With many projects going at once we found ourselves needing to visit our local marine supply store several times per week, and having multiple shipments on their way to us at all times. The luxury of our home base allowed this convenience which our new lifestyle will not afford us again.


Exploring in San Francisco

After we decided that we would leave earlier than previously planned, we had less than 6 months to complete the projects that were necessary to do coastal cruising, so we needed to prioritize our remaining work.

A trick we use in the project management profession when the circumstances allow is to reduce the scope of what is needed in order to be able to succeed at an on-time delivery. This approach has worked perfectly in our case. We identified which of the remaining projects were actually essential right away, and which could wait for a later time after our planned departure date of late June. Then, we simply focused our limited time on the highest priority tasks and projects, and put the others on the calendar for a later time.


I realize now that we didn’t spend enough time with our family and friends, just having fun. This is what we expect our lives to be about as soon as we leave, visiting new places, making new friends and connecting with old ones. We didn’t take a dip into that part of the cruising lifestyle as much as I now feel we should have.


I knew it would take work and some discomfort to prepare for and take on this lifestyle but occasionally I found myself thinking something like, “I just need to wait until this part is over, then I can experience the good stuff.” Sometimes it took a while, but I always would come around to realizing that it’s all good stuff or that I could make it good, through action or reframing.

Looking at the fish finder

This would happen when I donned my teal-colored glasses, those that I acquired when we decided that we’d make this dream a reality and could picture ourselves in the warm blue-green sea. They let me see how fortunate we are to have the opportunity to choose this lifestyle and feel gratitude for each other and everyone else who has supported us along this journey. They help me recognize that the present is fleeting and that allows me to put any woes into the broader perspective. Then I recognize that life is good. Always.

The Final Stretch

Getting comfortable

At this point, mere days before we embrace the cruising lifestyle in earnest, I feel at ease. I realize that I’m feeling calm because we’re ready – not perfect, but ready to take on this next challenge of becoming cruisers.

We’ve worked hard to get to where we are now. We still have outstanding projects, but this will always be the case, and they will be pursued over time and as needed.

As Erin Skye’s deck slowly sways along with the movement of the sea, so now do our expectations. The transition from land lubber to cruiser is not yet complete, but we are well on our way. We can take pride in the fact that we have a clear view of the ocean’s promise, and have pursued our dreams.



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Written by Deanna