“Twenty years from now you will be more disappointed by the things that you didn't do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” – Mark Twain

The Hardest Part


In countless blogs and books we had read that getting off the dock is the hardest part. That now makes so much sense. Between the stress of saying good bye to friends and family, the stress of getting the boat ready ( well, as it will be) and the stress of the unknown it can all add up to conspire against actually leaving.

We worked to set us up to minimize this as much as possible.  This last summer was not the most fun boating season we have had.  Many days we watched our friends head out for a fun day on the water while we stayed tied to the dock working on projects.  Even the times we left, projects followed.  We rafted up with friends out at World’s End and we would alternate between working on projects and having some fun. We knew we were being ambitious with our Epic To-Do List.  An no, we didn’t finish everything on it.  But we pushed to get the safety items done first, followed by some comfort items.  We made this push early because we new the last month would be much harder to get things done.

We also knew that the boat would never be done.  If we waited for the boat to be perfect we would never leave.  Smitty is more than serviceable and we could probably take her all the way to the Vigin Islands without doing much more.  But we will do more.  There will be rainy days or bad sea days or days we just don’t feel like traveling where we can work to get other things done.  We have a list going of things that need to be fixed or projects to do.  I have a box of parts for various projects.  Eventually we will get through most but new things come up while you are cruising and new priorities are set.  Like Captain Ron says…

The last month was filled with friends and family.  We had cookouts, dinners out, lunches and drinks with colleagues and even a good bye boat trip to Gloucester with our friends from L Dock.  That even continued into the trip.  I am finishing up this post about 2 weeks after leaving and we are sitting in Milford, Connecticut to see my Bride’s family.  We will do a separate post on saying good bye, but as a preview our friends from L Dock gave us the board below.

Yup, that’s the eight from our Slip 8 post.  Our friends conspired to steal the “8” from the dock after we left for our annual trip to Gloucester.  While in Gloucester they gave us the board that they had all signed and put the “8” on.  It was a very touching gift and it had my Bride in tears (I might have been a little teary eyed too).

What we read was soooo true.  Cutting the lines and heading out for that first day was the hardest part.  There were lots of things pulling you back.  Trying to get you to delay the departure.  At times it was a struggle to keep the motivation going to work towards the departure.

The whole thing felt surreal.  A mix of feeling like you were just getting ready for vacation and “is this really my life now?”

On September 4th at 03:20 we departed Hingham Shipyard.  There was very little moonlight as we powered into the darkness.  The lack of moonlight was probably a good thing.  It kept us focused on spotting for lobster pots and other obstacles instead of thinking about what we had just done.  At around 05:30 we started getting the predawn sky with enough light to see any obstacles coming.

With that beautiful sky came time to think.  Time to reflect on what we just did.  We were 40 years old (my Bride was not technically 40 for another week and a few days). We had quit well paying jobs that we were unhappy doing.  We had packed up all of our shit onto our little 31 foot boat.  And we sailed away from our friends and family into an adventure of unknown duration or true destination.  And all of this financed by a relatively small cruising kitty.

It’s an unknown feeling. Extremely hard to describe. I’m still unsure about how I feel. For the first week or so it felt like being on vacation. Now its starting to change but I don’t know what it feels like. But that is part of the adventure: new feelings; new experiences; new adventures!

6 thoughts on “The Hardest Part

  1. Congratulations to the two of you. We are wishing you many fine adventures and hope the cruising life is everything you have ever dreamed.

  2. That is such a cool gift! So happy for you guys that you’re on the way down south. Hopefully, we’ll see you somewhere in the Caribbean this coming season!

  3. Congratulations! I understand it just gets better from here on out.
    You two are smart and I’m sure that you’ll figure out how to keep growing the kitty while sailing.
    All the best!

  4. It may have been the hardest part, but you guys are one of the very few who managed to do it AHEAD of your schedule. Breath, pat yourself on the back and settle into your new lifestyle 🙂

  5. Congrats on leaving the dock! We’re about 6 months behind you, and we’re definitely feeling the emotional pain of making the dream a reality. It’s difficult to go against everything we were taught nd quit working at ave 49 .. more difficult for Ken than me. It’s both scary and liberating. Life’s an adventure right?!

    We look forward to reading more of your thoughts about your new life. I imagine it’s very surreal.

    How is the dinghy sling working out?

  6. Pingback: 2015 in Review |

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