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The grass is always greener on the other side of the fence. I hypothesize that it’s this widely-held belief – that someone else’s circumstances are better than yours, or that which exists somewhere else, or doing something different will be an improvement – which leads most people to the cruising lifestyle. Conversely though, I also think that much of a cruiser’s stress can be summed up in that phrase, specifically the inability to get to those mythical greener pastures.

For example, at this very moment, we know several cruisers who are waiting for a weather window to sail someplace new. Mother Nature, being herself, typically doesn’t concern herself with cruisers’ travel plans. She does what she wants, which at this time of year, in this area, means that she makes the wind blow and the seas bumpy. In other words, not ideal for sailing. Similarly, we know a few other cruisers who are working through boat issues (hello!), problems that are preventing them from traveling where they’d like to go. This can also be stressful. Even sailors who are underway, when faced with inclement weather, may long to be someplace else. Sometimes this can be seriously stressful!

Related post: To remain happy go easy on the comparisons

Unfortunately, as the proverb implies, the grass is not always greener on the other side. Some people find that after changing, they prefer what they had initially. In this case, some who set off cruising find that the lifestyle is not for them. Just recently I encountered such an individual, a reader of this blog as a matter of fact, and it made me sad to see how much he had invested, only to be disappointed by the outcome. Perhaps it’s the fear that this will occur that keeps many folks in the planning stages?

I can offer no real solutions for any of this. Of course, a potential cruiser could test the waters by taking a liveaboard sailing course like we did, or chartering a boat for a couple of weeks. Both may help, but I fear will never be 100% foolproof. As for the stress that comes with not being able to move when you wish, adopting a Buddha-like attitude may be the only solution. Then again, maybe we don’t want a solution? Maybe it’s that drive for greener pastures that keeps us all moving forward?

Time for another cup of coffee. Enjoy your day. 🙂


  1. Well, being able to read your blog and others certainly provides insight into some of the realities ‘on the other side of the fence’. Thanks for that.

    • You’re welcome, Brian. I do my best to paint, what I feel is, an accurate picture, a balance between the fun stuff, and the sucky stuff.

  2. Interesting timing. We left out 10 days ago and have been traveling the Gulf coast ICW (GIWW). We have been asking ourselves a lot of these same questions. We have decided not to make any major decisions right now as we know traveling the ICW is not what we really signed up for and the stretch between Galveston and New Orleans is the roughest part of the GIWW. And we are getting more comfortable with our skills and boatsmanship. But the questions do linger: Is this too hard for us? Is this what we really want to do? We though that we had answered these questions, but we are now asking them again.

    Mike & Vicki
    S/V Krakato

    • I don’t know you Michael but I can virtually guarantee, it is not too hard for you! Whether or not it’s what you want to do though, that is a question only you can answer.

      To give you some more insight into my thinking on this post, we have a couple of friends who have been cruising for 10 years. They now are looking to sell their boat, and plan to purchase an RV to continue their adventures on land. I have to imagine that, because they have already moved on in their minds, being held back from being able to sample that “greener grass” is somewhat stressful for them. I know that it would be for me.

      Where are you hoping to travel to?

      • Heading to the Eastern Caribbean at some point. Right now just trying to get to Florida and across to the Bahamas. Then it will be down the Thorny Path to the EC.

        I’m pretty sure I’d feel better there than here dodging all the barge traffic in the ditch, having to motor everywhere and dealing with bridges and locks. Of course if this all doesn’t work out for us, the RV thing is the backup plan.

        • Give it a chance, Michael. I promise, the crystal clear waters of the Bahamas will make you forget all about the ditch (which we didn’t mind, by the way). 🙂

          • That is what we keep telling ourselves at the moment. At least we are in a marina for the next few nights to catch up on boat chores, laundry, … So hopefully a few good nights sleep (no anchor watch!) will help a lot as well. 🙂

            • Hopefully this makes you feel better, but unless it’s blowing over 40, we sleep very soundly. We may not have initially, but we do now.

  3. Very good point.

    But, 😉 , that feeling that the grass is always better over the mountain or across that sea has led to a lot of exploration and adventure.

    Just saying.

    • I agree, Arty. That was pretty much the sentiment I was trying to convey at the end of the final paragraph:

      “Then again, maybe we don’t want a solution? Maybe it’s that drive for greener pastures that keeps us all moving forward?”

  4. The grass usually is greener on the other side … because of all the manure!

    If you can live with the manure, then the other side may be for you ;-p

  5. There is always manure on both sides I recon. The manure on your side is part of what makes the grass “appear” greener because our rose tinted glasses filter out the manure on the other side if we are even aware of it.

    The trick is to count your blessings and not your curses, making the best of where you are in your life now. Dream of tomorrow, but be present in the moment today.

    “Comparison is the thief of all joy” ~ Theodore Roosevelt

  6. Have you tried living for the journey and not the destination?

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