Part-time Cruising….how we do it

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Sailing is in my blood. Well maybe its not the actual sailing – lets say the cruising lifestyle (although I wouldn’t want to do this with engines as my only means of propulsion). Almost any couple who desires this life of untying the lines and heading to somewhere exotic is faced with the same dilemma. Not enough time, not enough money, not enough experience, kids are too young, kids are too old, you are too old or the onset of health problems…yep that’s the big one and the only one that may really stop you in your wake. Now these are all real world problems, yet each year hundreds if not thousands of people get out there and do it. I have interviewed many. They all have the same issues as mentioned here but somehow they take the leap.

I have read and watched hundreds of blogs, books and videos from cruising couples doing what they do. Lennie and I always assumed we would do it when we were “older”. Then when our last kid left for college everything changed. We weren’t homebound to avoid high school parties anymore. That’s when we bought our first boat in the Caribbean and began traveling once a month. Back then we did it from Wednesday to Sunday so it was more of a long weekend. After a few years we decided to buy a bigger boat and take more time off. This presented a challenge. I had to find a way to spend more time out of the office and Lennie (a General Contractor) had to decide how many houses she could build “part time”.

Our answer was transition. A simple but powerful word. We both assumed (since we are self-employed) that their would be no retirement party at the dock with hugs and goodbyes but a slow deliberate plan to spend X amount of days per month on the boat, moving it from port to port and flying back to work in between. We recently bumped it up to one week per month. I don’t think anyone even noticed at work. My managers have been with me for 20 years so they pretty much know what to do. They have a system in place called “R.O.B Protocol” which means “Randy on boat”. Lennie, on the other hand, has been building custom spec houses, which take a lot of physical boots on the ground. She is beginning to change her focus more to buying and selling real estate and smaller projects instead of ground up construction. Some members of our family were a bit nervous at our being gone so much, but now they have accepted it and the many invitations to join us wherever we are. The biggest issue is not how to do it but the decision “to do it” and once that is made you will be amazingly creative.

People we meet have three questions . Yes the same three.

  1. Where are you going
  2. For how long are you going
  3. What do you do for a living/are you retired

The answers:

  1. We don’t know
  2. We don’t know
  3. Work hard/nope

Yeah….we are not very helpful because we don’t want to box ourselves in. I guess if business got bad we would have to spend more time at work. But one thing is for sure. We have spent 60 days on the boat in the last 5 months and we don’t regret one of them

This video shows my team of managers. I can’t give them enough credit.


4 Responses

    • happytogether

      Thanks Susan. And thanks to your husband who helped make it possible!

  1. steven

    Just finishedyour YouTube videos. I have followed many, Delos and Vaga and look forward to new posts (yes I am a PATREON). living vicariously through them, wonderful experiences. However it is you and Lennie that myself and Lisa identify most with. Soon we hope to meet you both and share a wonderful evening on our own boat (yet to commit to one). Steven.

    • happytogether

      Steven, Thanks so much for your email. I appreciate the good feedback for the effort we are putting in. I hope you and Lisa make the leap soon!

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