The Dream

It's not that I'm only happy when sailing... but I'm always happy when I'm sailing. There's just something so visceral of using the power of the wind to propel our vessel through the water. Without a doubt my favourite moment is when I turn the engine off and hear the just the sound of the water rushing past the hull. So pure.

Every summer I would sail with my cousin on lake Champlain in upstate New York / Vermont. It just was not summer until we sailed. I have defining memories of being very small on a Sunfish dinghy with my cousin and my father. I of course had little idea of what I was doing and had no concept of “lift” or tacking vs. gybing but it I just knew it was great! Fast forward to turning 30 and reflecting on where I was and what I wanted in this life; “I'd love to retire on sailboat in the Caribbean! Life's too short why wait to retirement to start." The learning curve is actually quite long and retirement age would just not do! Research commenced and the more I learned the more I was inspired. Turns out many people are doing just this (including many Canadians) and sharing their stories on the internet! I was particularly inspired by Theresa Carey's Sailing Simplicity and the Pursuit of Happiness.

While I do absolutely love my home city Montreal, a city with a “joie de vivre” unique to North America and the “city of festivals” in the summer, I am not a fan of the long cold winters we endure.
The plan ultimately is that every September as the temperatures dip we will head down the eastern seaboard visiting various friends & family along the way and interesting ports of call (NYC, Atlantic City, Myrtle Beach, Savannah, Miami, etc.). Once in Florida, likely around December we wait for a weather window and head across to the Caribbean. Enjoy the coldest winter months December, January, February island hopping and hosting friends & family who fly down for a cheap vacation. When the weather starts to heat up again (the Caribbean can be brutally hot in the summer months) we turn our bow north and start heading back up the eastern seaboard arriving back in Montreal around June just in time for summer and to see friends and family we've missed.
Transiting up and down the eastern seaboard we could alternate between ocean coastal sailing and the intra-coastal waterway (ICW).
Also one alternate plan is to cruise the winter months in Mexico instead of the Caribbean. Cassandra speaks Spanish and has previously lived in Mexico on a student exchange program. She speaks very highly of it. This would also limit the customs headaches (and costs) of Caribbean island hopping. There are some interesting blogs of cruisers in Mexico who expound the great food and the low costs of everything.

We'd love to hear your thoughts, comments and advice about our ambitions so please feel free to add a comment below or send us an e-mail.


  1. Fantastic plan! Just what I'm planning too; sooner rather than later as well. Keep up the great blog!

  2. Congratulations on setting off on your journey. Your dream tab will need to be renamed "reality"!

  3. Wishing you smooth seas and steady winds - Steve and Sue Stamm

  4. This comment has been removed by the author.

  5. This comment has been removed by the author.

  6. It was cool to meet you two in George Town . Good luck with your voyage and I wish you the best!

    -Chris and Peter from LIfesong