“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

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Last Week

One week….

Very strange and mixed feelings.  It’s Monday morning of our last week of full time employment.  We’ve both had jobs of some sort since our teens. Since graduating college I have basically had the same morning routine: wake up, take a shower, walk the dog(s), get in the car, get a coffee, sit in traffic (anywhere from 30 minutes to 2 hours).  It will be really strange to not have this morning routine dominate my life.  But there is still a lot of work to get done in this last week.

Our last two weekends have been filled with get togethers with friends and family.  Many of whom we won’t likely see for several years.  Seeing relatives and friends, eating some great food, sharing old stories.  It’s bitter sweat to see everyone and know we won’t see many of them again for some time.


Project wise it has been a bit of an epic fail.  My Bride somehow managed to climb into the back of the boat to change out the fuel tank sender unit.  But this didn’t fix the problem and another hour of trouble shooting still hasn’t identified the source of the malfunctioning fuel gauge.  We tried to fix the holding tank level sensor but no luck.  Still have piles of stuff we need to find space for on the boat.  This week will be a busy one between work and dealing with the last of our stuff.

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One Month!

It’s August 4th and within 31 days we will be unemployed, full-time cruisers.  We started this blog more than two and half years ago with the dream of quitting our jobs and heading off cruising.  We are now one month from fulfilling that goal and moving on to the first real big adventure of our lives.

We only have one more “must complete” project left, the long overdue maintenance to the steering system.  After that we have a couple of “it would be nice” projects that we would like to get done while it’s more convenient but they could be finished along the way as well.


Some of the last sunsets we will see from our slip in Hingham.


Officially Captains

I wrote back in May that Smitty Now Has Two Captains. That is when we had passed our tests and received the certificates from New England Maritime.  Shortly after that we submitted the actual paperwork to the US Coast Guard.  After going back and forth a couple of times about the medial forms that the doctor had filled out incorrectly, we have finally been issued our Merchant Mariner Credentials.


Here’s the funny thing. We literally submitted the exact same application. I did the sea time form once and just changed the name on it for my Bride.  All of the information was exactly the same….

We applied for 25 ton Master on inland waters and OUPV on Near Coastal Waters (this is “off shore” based on how the USCG handles these things).  I received a credential for a Master of up to a 50 ton vessel.

j lic

However, my Bride received a credential for a Master of up to 100 ton vessel.

S Lic

I guess this makes her the true captain of s/v Smitty!


Departure Dates, Corporate Life and To-Do Lists

One of our biggest motivations for wanting to cruise is the rejection of the corporate life.  Neither of us are happy getting up every morning to commute to a box to sit at a desk and stare at a computer screen.  I know, we should just suck it up.  That’s part of being an adult. How else are you supposed to live?  Blah, blah, blah!  We’ve already established that we reject those assertions.


But we have been letting our corporate lives control one aspect of our cruising plans: the departure date.  Our October 17th date for cutting the lines was based on a work thing.  It was based on my Bride’s bonus which is typically paid out on at the end of September.  Her company has made it clear that if they know you are leaving the company for any reasons….no bonus for you!

So our plan was get the bonus in the account, give two weeks notice and then cut the lines. This meant we were leaving a little later than we would like and we would end up rushing south until we were ahead of the cold.  So we wouldn’t be relaxing and enjoying our time until we got to around the Carolinas most likely. Based on some recent events we have figured out that the bonus is not likely to be as large as past years and our expectations.  This brought up discussions of not waiting for the bonus. After much deliberation we have decided to forgo the bonus and leave earlier than expected.

Our new departure date will be September 8th!

That means we have just a mear 64 days before we go.  Only 44 work days at our jobs! Holy sh@t that seems close.

A little explanation of the new date. For the past 4 years or so on the Labor Day Weekend we have done a trip to Gloucester with a large group of boats.  Last year there were 18 boats that made the trip.  We had already booked the trip for this year and over 20 boats are expected to go. So we decided that a Labor Day Weekend trip with friends would be a great way to celebrate our escape from the corporate world.

Now the downside of this is that it compresses our to-do list time frame.  Originally, I was going to stop working about a month before my Bride and that would give me time to get some stuff done. Now we have just 8 weekends and what ever time we can fit around working to get things done.  We understand that no boat will ever be “done” and that there are plenty of things that can be done along the way. So we aren’t overly stressed.  But there are some things that will have to be (or we really want to be) done before we go.  So here is our short list of things we need to work on:

  1. Check Dates on Flares
  2. Install Port Visors (2)
  3. Add Anchor Chain or system to prevent keel wrap
  4. Install the Sonarphone from Navionics
  5. Install Stern Anchor and Line Holder
  6. Check Steering Cables
  7. Install Inverter
  8. Install 12 volt outlet at Helm
  9. Rebuild Winches
  10. Cockpit Table Upgrade
  11. Tune Up Outboard
  12. Install Tank Sensors on Holding Tank & Water Tank (about half done)
  13. Change Head Intake Plumbing & Fix Leak on Head
  14. Security Doors for the Companionway & Bars for Large Hatch
  15. Organize & Store All of Our Parts & Supplies Stored at my Office, Sell the Rest
  16. Summer Vet Checkup & Get Full Copy of Vet Record
  17. Apply for Bahamas Import Permit for Summer
  18. Close PO Box
  19. Donate or store work clothes
  20. Sell Car


Smitty Now Has Two Captains!

Sorry again that our blog has had little activity but I can tell you it has been for a reason.  For the past couple of months all of our non-working hours have been consumed with taking classes to get our captain’s licenses.  This past Saturday we passed our final exams and we are both certified as Masters of up to 100 Ton Vessels. We need to submit our applications to become licensed but they are done and it’s just a matter of sending an email to the US Coast Guard with all of the info.

JK Master 100 T STK Master 100TWe are so glad this is done. It took way more time and effort to get this done than we thought it would.  The classes were every Monday, Wednesday and Friday from 6-9:30.  We also had to do homework almost every off night and on weekends.  Near the end we just wanted the whole thing to be done and over because it felt like it was consuming our whole life!

We initially decided to get our 6-pack captain’s licenses due to a conversation with our insurance company.  They said we would either have to hire a professional crew for our crossings or pay twice the rate.  When we looked at the cost of getting our license vs. the increased cost of insurance it seemed like a no brainer.  The 6-pack allows you to take up to 6 passengers on an uninspected vessel and is actually call the Operator of Uninspected Passenger Vessels (OUPV). They are further classified as Near Coastal or Inland based on your boating experience or sea time.  You need 360 days of sea time to qualify for the Inland and 90 of those days must be beyond the “Boundary Line” if you want the Near Coastal.  Luckily the “B” Buoy is the local edge of the Boundary Line and we often sail out beyond this area.  When I added up all of our time on Smitty and Splash we have 464 total days with 153 being beyond the Boundary Line.

Image from here.

Image from here.

Once we started the course it seemed like getting the 6-pack was kind of foolish.  The difference between the 6-pack and the Masters is only 2 and half weeks of class and you have 10 additional questions on one part of the exams.  Also, after talking to a couple of the instructors it looks like it will be relatively easy to pick up some work along the way with the Masters license that will help keep the cruising kitty going.  So we paid the extra $150 to upgrade to the Masters.  Based on our sea time on Smitty (a 7 Gross Ton vessel by USCG standards) we should qualify for a 50 Ton Master’s Inland and OUPV Near Coastal.  This would mean we could deliver private yachts going offshore up and down the coast and work on larger boats like ferries, working boats, launch tenders, etc. inside the Boundary Line.

We both also got the sailing endorsement, which allows us to operate sailboats.  For that we needed 180 days of experience on a sailboat.  That was no problem since all of our days were on a sailboat.

I also decided to get my tow endorsement.  This would allow me to work for an assistance tow company like Tow Boat US or Seatow.

Here is a little outline of the process.

  • 10 weeks of courses Monday, Wednesday and Friday from 6-9:30 and you must attend 90% of the classes to sit for the test (school rule)
  • an additional 4 hours of course time for the sailing endorsement
  • an additional 4 hours of course time for the towing endorsement
  • Pass all the exams
    • Rules of the Road – 30 questions, no resources, 90% correct required to pass (hardest test for most)
    • Navigation General – 20 questions, you can use the Pubs and CFRs, 70% correct required to pass
    • Plotting – 10 questions, you can use the Pubs and CFRs, 70% correct required to pass (actual paper chart plotting including taking wind and current drift into account)
    • Deck General – 70 questions, you can use the Pubs and CFRs, 70% correct required to pass (this is only a 60 question test for the OUPV)
    • Sailing Endorsement – 20 questions, no resources, 70% correct required to pass
    • Towing Endorsement – 20 questions, no resources, 70% correct required to pass
  • USCG Physical & Drug Test – This includes some different stuff than your typical physical like a test for being color blind, a functional hearing test and it has to be on their specific forms
  • Get a Transportation Workers Identification Card
  • Get 3 Letters of Reference from non-family members

We could have studied on our own and just went into the USCG office in Boston and took the exams.  Given the info that was on the exams we felt the best option was to take a review course.  We went with New England Maritime; they are out of Hyannis but have a satellite location in Quincy.  I am really glad we went with the course.  We learned a lot of good info that isn’t covered in the exams but we should know.  The main instructor, Charlie, was great and really prepared us well for the exams.

Another step to leaving the cubicle life behind us!


Intimidating Conversations

Yesterday was interesting.

I work for a medium sized environmental consulting firm.  They have multiple offices up and down the east coast and about 150 employees.  My little corner of their world is only 16 employees of which I am one of the 4 senior staff members. I have told the people that work in the office that I am leaving but none of the corporate folks were aware.  We have been working on a transition plan for when I leave and it was time we told corporate.

For me this couldn’t have been at a better time.  I have really been hitting a good stride work wise lately.  While I don’t like my job and I don’t want to do it anymore, I like to think I am really good at it.  In the last year, one of my biggest clients from my previous company, the largest school district in the state, brought their work to me over my previous company.  I have also been getting new work all over the place from local colleges, architect and contractors.   This is great because the company has been considered more of a petroleum consulting firm that caters to big oil companies and this work I have been getting greatly diversifies the work.  On top of that, I have been able to get this work at better profit margins than many of our other clients.  I also run the construction and emergency response side for one of our major petroleum companies.  This is a fast moving and stressful part of our portfolio but I have had this side of the work running great. Recently the company put out a report on the state of the company and our office had some of the best numbers in the company and we are setup to have one of the best years in the company’s 22 year history.  I like to think I am a big part of why our office is doing so well.

So we requested the owner and CFO of the company come up from the Long Island headquarters so we could discussion senior staffing.  We told them I was leaving and what our thoughts were on how to replace me.  Overall the conversations went well.  But it was very intimidating to sit down with them and say that I am going to leave the company in several months.  There is always the possibility they tell me to go right there and then.  That could be a big blow to the cruising kitty.

It’s also a little like being present at your own funeral.  You sit there and listen to people breakdown your good and not-so-good attributes as they determine how to replace the work you do.  They ask you questions trying to get into your head and understand how I can balance the work I do.

Of course there was that moment where the owner of the company said he wished he could do this.  Biting my tongue and not yelling at him that he has millions of dollars and could do it if he chose to was the toughest part of the whole day.  We hear these types of response often and I find them very frustrating.

We are not independently wealthy.  We don’t have trust funds or large savings accounts or any other type of cushion.

We have an affordable boat that we love.  We have thoughtfully outfitted her.  But, to steal a recent line from another cruiser/blogger, we have made the choice to live A Life Less Ordinary.  This doesn’t happen by magic or accident.  It has taken enormous thought and dedication to get to this point.  It will take even more to get to the point of cutting the lines.

Interestingly as we near the endpoint in this part of our journey, only 163 days until we cut the lines,  there has been a flood of reaffirming articles making their way around the interwebs.  There was the piece from the Tiny House blog from Jody of Where the Coconuts Grow (linked above).  “Out on the ocean everything is simple. Elizabeth noticed how obvious it became to her that we can always do with less.”  A number of people on Facebook have been sharing the Elle article Why I Gave Up a $95,000 Job to Move To an Island and Scoop Ice Cream. Yup, doing that times two.  Then my Dad shared an article from Fast Company entitled The Science of Why You Should Spend Your Money On Experiences, Not Things.  “Our experiences are a bigger part of ourselves than our material goods. You can really like your material stuff. You can even think that part of your identity is connected to those things, but nonetheless they remain separate from you. In contrast, your experiences really are part of you. We are the sum total of our experiences.”