“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 Plan

We are in year two of a five year plan to become live aboards and cruisers.  We have always loved the Caribbean since our first visit in 1996. We were married on St. Thomas and have gone back as much as we could afford. That is our planned destination. But we want to spend some time getting there and explore the East Coast along the way. The plan in its basic form:

  1. Get a bigger boat (December 2010) – Check
  2. Learn how to maintain all the systems in the boat (2011-2012 sailing season and ongoing forever) – Check and ongoing
  3. Live aboard for a summer to see if we like it (summer 2012) – Check, Loved It!
  4. Declutter the house and get rid of the stuff we don’t want to take on the boat (winter 2012-2013) – Check but took a little longer
  5. Sell the house (spring 2013 as long as we are not underwater) – Check, Closed on our house in May of 2014
  6. Make upgrades to our boat for living aboard in the northeast (2012-2013) – Not Done Yet.  I better hurry up! The boat is as ready as she will be.
  7. Become full-time live aboards on our Catalina 310 (spring 2013) – Check
  8. Build the cruising kitty (2013-2015) – Need to work harder!  I like to spend money too much. We reached our savings goal! 🙂
  9. Leave to head south on June 26, 2015 (my 40th birthday) – Slight planned delay until October of 2015 to wait for my Bride’s bonus that is paid out at the end of September We are departing about a month and a half earlier than this plan.
  10. Go south until the kitty runs out (2015-?)

The plan has been executed and we are out cruising. We are loving every minute of it and it has been worth every ounce of hard work and sacrifice.

8 thoughts on “The Plan

  1. We love the plan. We hope to see you “out there” one day soon. Our plan was a little more lengthy. We started with our concept of sailing to distant far away places about 30 years ago and have stayed the course to make it come true.

    We are of the same mind set about careers defining a person. Mark posted this on his About Mark page “You’ll notice I skipped over the whole career part. For me, working was nothing more than a way to provide a lifestyle. That’s all. It was not an identity. It could have been at one point. I once drank the company Kool-Aid. I was gently grounded by Cindy”

    We’ll save a bottle of wine for when we meet you anchored in a cove one day.

    Mark and Cindy – s/v Cream Puff

  2. Thanks for reading.

    It’s funny, you do tend to run into a lot of people with the same mind set in the cruising community. I guess that is part of the draw of the cruising lifestyle, moving away from the “standard” existence to live a life less ordinary.

    Wow! Cream Puff is a nice sailing vessel! She looks fast and sturdy.

    Definitely hope we meet up and have that bottle!

    Fair winds,


  3. Just found your blog through The Red Thread—sounds like a great plan! We love the Caribbean, too—didn’t spend enough time there on our old boat, have to go back at some point! Good luck with everything and looking forward to following your posts!
    Ellen and Seth
    s/v Celeste

  4. Pingback: 989 Days |

  5. Great to see people decide to go cruising before age catches up to them. Too many people wait for the right time and end up never doing it. I quit my job in 1987 and sailed for 2 years on my 1970 Columbia 26 to Bahamas, Caicos and Dominican Republic. Went back to work in 1990 and in 2012 bought Hull#57 Catalina 310 Sweet Pea with my new wife. We retired in 2013 and live on the boat in Florida. Will be going to Bimini Bahamas next week. Maybe we will see you in the Abacos 2016 will be spending several months there. Great to hear of people doing there dreams, have received several answers to my post from you on the forum, thanks.

    Mark & Joy

  6. Hi guys, this is mike cafferty, I’m good friends of Chris and liz. So happy for you guys . Was working with Chris today and told him to tell you guys if you didn’t make it to milford today my mooring in stony creek was available for you to tie onto . well, I’m leaving late October and heading to marathon key for a bit, before ? well… who knows …maybe we will share a cocktail somewhere warm… fair winds and following seas

    • Hey Mike,

      Chris and Liz told us about your plan. Make sure you check out where we are on the “Where is Smitty” link and let us know if you are in the same area. We would love to get together.

      Fair winds and good luck with your departure.


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