To Sail Or Not To Sail – What We Did On Our Summer Vacation

Imagine this

We have been imagining this a lot.  One night Lori and I were discussing the inevitable.  You know, the day when cash flow changes and you are retired.  We are at the point of serious consideration now and we are exploring possibilities that both give us what we want and do it within financial reason.  Lori brought up sailing.  Not just any sailing, but live-aboard sailing.  The kind where you are truly free of encumbrance, the kind where you go where you want, when you want and bring your home with you.  What brought this on was a progression.  We originally thought RV.  The killer there is fuel and the ability to get around once you got where you were going.  Big bucks.  Then we thought, wind is free.  You move a lot slower, but we would be retired, so who cares.   An interesting concept and one which we have used as a template for our summer travels this year.  We have been to several spots and have a lot to do and learn before we make a decision on whether this can be done, or even doable from a skill set position.  We have sailed in the past, but nothing close to this vision.  Will we be able to sail a 40 footer, will we be able to pass the necessary courses to be able to skipper a boat, where do we practise, what do we buy.  A million things to do and think about.  Over the next few years, we need to have an answer to these and any new questions that may pop up.  And I will be documenting every bit of it for us to remember, and by virtue of vicariousness of blogging, so will you the reader.

This first post is an introduction to my thinking on this topic and an opportunity for you to tell us we are crazy, or crazy like a fox.  Personally, I see this as a major challenge, one that I truly want to succeed at.  We love to travel, and we want to see everything.

Sailing in the sunset

Sailing in the sunset (Photo credit: jimtsap)

About John

I enjoy travel, sports, music (a dedicated site at and anything else that jumps up at me for the moment, which is why I blog. There will be lots of travel posts, pictures and our videos as well as a smattering of sports and humour. I enjoy promoting Canada and am unabashedly a proud Albertan

Posted on September 17, 2012, in Sailing, travel. Bookmark the permalink. 20 Comments.

  1. Sailing always sounds so exciting! I will live vicariously through your blog and process, considering my stomach will never attempt it!

  2. I like this idea! I think it would be such a huge undertaking, though. It seems right for the two of you who love to travel. It’s not like you’d be sailing around the world in a race. You could just be very leisurely. I bet if you start asking other yachts man, they’ll give you the pros and cons. I like your sensible approach, John. I’ll be curious to see what you finally decide. (Perhaps I can interest you in a lovely home in Barrington, Illinois? haha!)

  3. The video is so peaceful… ahhh… (until you start imagining all the creatures in the ocean!)

    • Simple. Catch em and eat em lol. There are lots of videos in YouTube. Some with dolphins and whales pacing the boat, some that will scare the crap out of you. All in all though an adventure is an adventure.

  4. Beautiful. The video was very calming. I can’t wait until my next vacation.

  5. That sound is one of my favorites… so relaxing… Challenges are good, and this seems like one worth doing. Can’t wait to follow along!

  6. I will be reading with both joy and envy.
    I have several books about living on boats if you have any interest.
    Also, before you sell the house and buy about, please rent and do a few multi-day sails so you can see if you really do like it. I’ve heard stories of lifelong couples falling apart after being isolated on a fiberglass plank in the middle of the ocean for a few days.

    Something to consider, as it really is a different life…

  7. Sounds like a wonderful retirement, of course, I love sailing. I think if you practice and do the charter thing a couple of times, you’ll know if it’s right for you. I’m looking forward to following your adventure.

  1. Pingback: To Sail Or Not To Sail – Now What « Is It Possible To See It All

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