
Recently on Facebook, a novice sailor and wannabe cruiser asked for the cons of the cruising life. When I saw Pamela Webster’s reply, I asked her if she’d expand her answer into a guest post.
If you ask longtime cruisers if you should go cruising, you’ll hear tons of positive stories about the wonderful life. Cruiser missionaries are happy to tell you about beautiful anchorages, interesting people, and the freedom that comes with a nomadic life on board.
But are all the wonderful experiences other cruisers experience proof that you’ll enjoy it too? And how can you know before up-ending your entire life?
Ask Yourself One Question
Here’s one question you can ask yourself to know if the cruising life is for you:
What are you hoping to get from cruising?
If your primary answers only include romantic notions like playing on beautiful beaches, enjoying cocktails in the cockpit, frolicking with dolphins etc. then you might be better off spending your money going on some wonderful cruising charters each year.
But if you also have some grittier goals, like challenging yourself, learning more about your relationship with your partner, gaining confidence in building new skills than you’re probably a good candidate to be a cruiser.
The beaches, cocktails, and dolphins will come. But there’s a tax you have to pay to enjoy them. And the tax is effort and challenge.
The people who love the cruising lifestyle (like myself) embrace the effort as much as they embrace the joys. And people who end up disappointed (like my husband) are the ones who feel it’s just too hard for the payoffs.
Of course, there are many styles of cruising from singlehanded ocean passages to month-long cruises of inland waters. And every one of them is harder than living in a house or apartment in a developed nation.
If you have any doubt that you’ll enjoy the cruising life, start with a less challenging plan, see if you enjoy the challenges you do face, and expand your adventure to suit your growing comfort level.
But if you like things being hard, exult in meeting a challenge, and look forward to growing then the cruising life is probably calling your name.
Answer it.

Pamela Douglas Webster cruises with her husband and dog in the eastern U.S. She blogs about life on board with a large dog at Something Wagging This Way Comes. She’s also my assistant here on The Boat Galley and has made huge improvements to the site since coming aboard last summer!
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Nica says
This is fantastic, Pamela. I love how you ask the question about intention – what do you want to get out of cruising? What a really helpful lens through which to view the lifestyle.
Cheers!
Idette Makar says
The way you answered the question is spot on to me. You explain in a manner that shows the two extremes and how it is fine to be at either extreme.
Thank you!!!